Ochem Final Review – Flashcards
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Approximately how long is a C?C single bond of an alkane?
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153 pm
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What is the approximate C?C?C bond angle in propane?
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109º
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What is the name of the linear hydrocarbon with the molecular formula C7H16?
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Heptane
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What is the name of the linear hydrocarbon with the molecular formula C11H24?
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Undecane
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How many hydrogen atoms are there in nonane, the linear hydrocarbon with nine carbon atoms?
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20
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How many hydrogen atoms are there in dodecane, the linear hydrocarbon with twelve carbon atoms?
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26
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How many constitutional isomers are there with the molecular formula C4H10?
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2
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How many constitutional isomers are there with the molecular formula C5H12?
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3
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How many constitutional isomers are there with the molecular formula C6H14?
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3
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(Study Review part 1 Questions 10-15,20 for nomenclature)
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c:
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Which of the following compounds has 1°, 2°, 3° and 4° carbon atoms? a. hexane b. 2-methylhexane c. 2,2-dimethylhexane d. 2,2,3-trimethylhexane
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D
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Which of the following compounds has only 1° and 3° carbon atoms? a. hexane b. 2-methylpentane c. 3-methylpentane d. 2,3-dimethylbutane
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D
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Know isobutane and neopentane. (Question 18)
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c:
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Study Newman projections (Question 21,22,23,)
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c:
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Which of the following cycloalkanes has the most ring strain? cyclopropane cyclobutane cyclopentane Cyclohexane
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Cyclopropane
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Which of the following cycloalkanes has the least ring strain? cyclopropane cyclobutane cyclopentane Cyclohexane
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Cyclohexane
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Which of the following alkanes has the highest boiling point? a. propane b. butane c. pentane d. hexane
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D.) Hexane
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Which of the following alkanes has the highest boiling point? a. 2,3-dimethylbutane b. 2-methylpentane c. 3-methylpentane d. hexane
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D.) Hexane
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Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups? a. cis-1,2-dimethylcyclohexane b. cis-1,3-dimethylcyclohexane c. trans-1,3-dimethylcyclohexane d. cis-1,4-dimethylcyclohexane
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B.) cis-1,3-dimethylcyclohexane
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What is the approximate dihedral angle between the two chlorine atoms in cis-1,2-dichlorocyclohexane? a. 0° b. 60° c. 120° d. 180°
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B.) 60º
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What is the approximate dihedral angle between the two chlorine atoms in the diequatorial conformation of trans-1,2-dichlorocyclohexane? a. 0° b. 60° c. 120° d. 180°
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B.) 60º
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Which of the following is NOT true regarding the properties of alkanes? a. alkanes are nonpolar b. alkanes burn in air to give H2O and CO2 c. alkanes are highly miscible with water d. the strongest intermolecular force between alkane molecules is the van der Waals interaction
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C.) Alkanes are highly miscible with water
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Which of the following statements is not true? a. Combustion of an alkane is an exothermic reaction. b. The heat of combustion of propane is three times that of methane. c. The constitutional isomers of C7H16 have different heats of combustion from one another d. The products of combustion of an alkane are H2O and CO2.
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B
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What is the approximate dihedral angle between the two chlorine atoms in the diaxial conformation of trans-1,2-dichlorocyclohexane? a. 0° b. 60° c. 120° d. 180°
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D.) 180º
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Which of the following is the definition of a pair of enantiomers? a. A pair of structures that are superposable mirror images of one another b. A pair of stereoisomers that are non-superposable mirror images of one another c. A pair of stereoisomers that are not mirror images of one another d. A pair of stereoisomers that have equal specific rotations
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B
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Which of the following is the definition of a pair of diastereomers? a. A pair of structures that are superposable mirror images of one another b. A pair of stereoisomers that are non-superposable mirror images of one another c. A pair of stereoisomers that are not mirror images of one another d. A pair of stereoisomers that have equal specific rotations
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C
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Which of the following is the definition of chirality? a. The non-superposability of an object on its mirror image b. The superposability of an object on its mirror image c. A molecule that has a carbon atom with four different substituents d. A molecule with a mirror image
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C
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Which of the following is the definition of a meso compound? a. A molecule with stereocenter centers which is chiral b. A molecule with stereocenter centers which is not chiral c. A diastereomer with no stereocenter centers d. A chiral compound with more than one stereocenter center
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B
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Which of the following statements is not true regarding pairs of enantiomers? a. They have identical melting points b. They have identical boiling points. c. They rotate plane polarized light in opposite directions d. They react at identical rates with chiral reagents
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D.) They react at identical rates with chiral reagents
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Which of the following statements is true? a. All mirror images are enantiomers b. All molecules that have stereocenter centers are chiral c. Isomers that are not superposable on their mirror images are enantiomers d. Superposable structural isomers are enantiomers
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C
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Which of the following compounds is a meso compound? a. (2R,3R)-dibromobutane b. (2R,3S)-dibromobutane c. (2R,3S)-3-bromo-2-butanol d. (2R,3R)-3-bromo-2-butanol
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B
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Which of the following statements regarding optical rotation is not true? a. All (+) enantiomers are dextrorotatory. b. All R enantiomers are dextrorotatory. c. All (?) enantiomers rotate plane-polarized light in a counterclockwise direction. d. All (+) and (?) enantiomers rotate plane-polarized light in opposite directions.
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B.) All R enantiomers are dextrorotatory
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Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations? a. ?COOH b. ?CHO c. ?CH2OH d. ?CH3
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A.) -COOH
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Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations? a. ?NH2 b. ?NHCH3 c. ?CH2NH2 d. ?CH2NHCH3
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B.) -NHCH3
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What is the correct order of the Cahn-Ingold-Prelog ranking of the following substituents as used in assigning R and S configurations of chiral centers? (higher ranking > lower ranking) 1. ?C?CH 2. ?CH2NH2 3. ?NHCH3 4. ?CN a. 3 > 4 > 2 > 1 b. 4 > 3 > 1 > 2 c. 3 > 4 > 2 > 1 d. 4 > 3 > 2 > 1
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c.) 3>4>2>1
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What is the correct order of the Cahn-Ingold-Prelog ranking of the following substituents as used in assigning R and S configurations of chiral centers? (higher ranking > lower ranking) 1. ?CH2OH 2. ?CHO 3. ?OCH3 4. ?OCOCH3 a. 3 > 4 > 1 > 2 b. 4 > 3 > 1 > 2 c. 3 > 4 > 2 > 1 d. 4 > 3 > 2 > 1
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D.) 4>3>2>1
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Which of the following is the correct order of decreasing basicity (stronger base > weaker base)? a. NH3 > MeNH2 > H2O > HF b. MeNH2 > NH3 > MeOH > CH4 c. NH3 > Me3N > H2O > MeOH d. CH3COONa > NaOH > NaOMe > NaNMe2
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B.) MeNH2>NH3>MeOH>CH4
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Which of the following is the strongest acid? a. CH3CH3 b. CH3NH2 c. CH3OH d. CH3F
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C.) CH3OH
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Which of the following is the strongest acid? a. HCl b. HI c. HF d. HBr
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B.) HI
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Which of the following is easiest to deprotonate? a. CH4 b. CH3CH3 c. CH2=CH2 d. HC?CH
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D. HC?CH
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Which of the following is the strongest acid? a. CH3OH b. CH3CHO c. CH3COCH3 d. CH3COOH
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d. CH3COOH
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Which of the following is the strongest acid? a. CH3NH2 b. CH3PH2 c. CH3OH d. CH3SH
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D.) CH3SH
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Which of the following compounds is the strongest acid? a. HF b. H2O c. NH3 d. CH4
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a.) HF
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Which of the following compounds is the strongest acid? a. CH3OCH3 b. CH3CH2OH c. CH3CHO d. CH3CO2H
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D.) CH3CO2H
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Which of the following compounds is the strongest acid? a. CH3COOH b. ClCH2COOH c. CH3CH2OH d. ClCH2CH2OH
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B.) ClCH2COOH
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Which of the following compounds is the strongest acid? a. CH3COOH b. FCH2COOH c. ClCH2COOH d. BrCH2COOH
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B.) FCH2COOH
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Which of the following compounds is the strongest acid? a. CH4 b. CH3CH3 c. H2C=CH2 d. HC?CH
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D.
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Which of the following compounds is the strongest acid? a. CF3OH b. CF3CH2 CH2OH c. CF3CH2 CH2 CH2OH d. CF3CH2 CH2 CH2CH2OH
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A.) CF3OH
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Which of the following compounds is the strongest acid? a. CH3CH2CH2COOH b. CH3CH2CHClCOOH c. CH3CHClCH2COOH d. ClCH2CH2CH2COOH
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B.) CH3CH2CHClCOOH
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Which of the following is the strongest base? a. NaOH b. NaCO3 c. H2O d. CH3OH
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a.) NaOH
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Which of the following is the strongest base? a. iodide anion, I? b. fluoride anion, F? c. bromide anion, Br? d. chloride anion, Cl?
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B.) F-
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Which of the following anions is the strongest base? a. CH3COO? b. HO? c. NH2? d. Cl?
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C.) NH2-
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Which of the following anions is the strongest base? a. NH2? b. NH3 c. CH3CH=N? d. CH3C?N
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A.) NH2-
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Which of the following compounds has the highest pKa? a. NH3 b. H2O c. HCl d. CH4
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D.) CH4
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Which of the following compounds has the lowest pKa? a. H2O b. HBr c. NH3 d. CH4
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B.) HBr
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Which of the following terms describes the reactivity of trimethylamine, (CH3)3N? a. Brønsted-Lowry acid and Lewis acid b. Brønsted-Lowry base and Lewis base c. Lewis acid and not a Brønsted-Lowry acid d. Lewis base and not a Brønsted-Lowry base
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B
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_________ acids donate protons.
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Brønsted-Lowry acid
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__________ accept protons.
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Brønsted-Lowry base
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Which of the following is a Lewis acid but not a Brønsted-Lowry acid? a. CH3COOH b. AlCl3 c. H2O d. CH3OH
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B.) AlCl3
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Which of the following is a feature of a Lewis acid? a. proton donor b. proton acceptor c. electron pair donor d. electron pair acceptor
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D.) Electron pair acceptor
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Which of the following is a feature of a Lewis base? a. proton donor b. proton acceptor c. electron pair donor d. electron pair acceptor
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c.) Electron pair donor
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Which of the following is a feature of a Brønsted-Lowry acid? a. proton donor b. proton acceptor c. electron pair donor d. electron pair acceptor
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a.) Proton donor
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Which of the following is a feature of a Brønsted-Lowry base? a. proton donor b. proton acceptor c. electron pair donor d. electron pair acceptor
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B.) Proton acceptor
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Which of the following has the highest bond dissociation energy? a. HF b. HCl c. HBr d. HI
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A.) HF
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Which of the following concepts can be used to rationalize the observation that acetic acid is a stronger acid than methanol? a. electronegativity b. resonance c. valence shell electron pair repulsion theory d. Pauli exclusion principle
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B.) Resonance
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H2C=CH-CH3 Which atom is preferentially protonated by a strong acid?
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H2C
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What is the approximate pKa value of HCl? a. ?7 b. 5 c. 16 d. 51
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A.) -7
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What is the approximate pKa value of acetic acid? a. ?7 b. 5 c. 16 d. 51
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B.) 5
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Which of the following has a pKa value of approximately 16?
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C.) CH3CH2OH
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Which of the following statements is not true? a. The position of the equilibrium for an exergonic reaction favors products b. The products of an exergonic reaction have a higher Gibbs free energy than the reactants. c. The equilibrium constant of a reaction for which ?G° = 0 is 1. d. ?G° = ?H° ? T?S°
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b. The products of an exergonic reaction have a higher Gibbs free energy than the reactants.
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Which of the following is a definition of the rate-determining step of a reaction mechanism? a. the first step b. the last step c. the step that crosses the highest energy barrier d. the most exothermic step
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C.) The step that crosses the highest energy barrier
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What is the approximate value of the C?C?C bond angle in propene? a. 90° b. 109° c. 120° d. 180°
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c.) 120º
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What is the approximate value of the H?C?H bonds angle in ethene? a. 90° b. 109° c. 120° d. 180°
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c.) 120º
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What is the approximate value of the length of the carbon-carbon bond in ethene? a. 121 pm b. 134 pm c. 142 pm d. 154 pm
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B.) 134 pm
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What is the index of hydrogen deficiency of a compound with a molecular formula of C5H10? a. 0 b. 1 c. 2 d. 3
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B.) 1
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What is the index of hydrogen deficiency of a compound with a molecular formula of c6h8? a. 0 b. 1 c. 2 d. 3
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D.) 3
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What is the index of hydrogen deficiency of a compound with a molecular formula of c5h9br? a. 0 b. 1 c. 2 d. 3
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B.) 1
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What is the index of hydrogen deficiency of a compound with a molecular formula of c6h7Cl? a. 0 b. 1 c. 2 d. 3
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D.) 3
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What is the index of hydrogen deficiency of a compound with a molecular formula of C6H15N? a. 0 b. 1 c. 2 d. 3
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A.) 0
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What is the index of hydrogen deficiency of a compound with a molecular formula of C6H12N2? a. 0 b. 1 c. 2 d. 3
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C.) 2
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Which of the following molecular formulae corresponds to a compound with a hydrogen deficiency of 2? a. c5h8O2 b. c5h10o c. C6H15N d. c5h10br2
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A.) C5H8O2
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Which of the following does not correspond to a molecular formula of a neutral compound? a. C5H5Br b. C5H7Cl2 c. C5H5Br3 d. C5H8Cl4
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B.) C5H7Cl2
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Which of the following does not correspond to a molecular formula of a neutral compound? a. c6h9NO2 b. c5h7n2O2 c. c8h12o3 d. C7H7N
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B.) C5H7N2O2
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Which of the following does not correspond to a molecular formula of a neutral compound? a. C4H8BrNO b. c5h9clN2O c. C7H14BrO3 d. c8h14ClN
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C.) C7H14BrO3
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Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds? a. ?CH(CH3)2 b. ?CH2OCH3 c. ?CH2CH3 d. ?CH2Br
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D.) -CH2Br
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Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning E and Z configurations of carbon-carbon double bonds? a. ?COOH b. ?Cl c. ?CH2OH d. ?CH3
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B.) -Cl
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How many alkenes have the formula C5H10? a. 4 b. 5 c. 6 d. 7
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C.) 6
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How many constitutional isomeric alkenes are there with the formula C6H12? a. 9 b. 11 c. 12 d. 13
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C.) 12
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How many isomers of 1,6-heptadiene exist? a. 1 b. 2 c. 3 d. 4
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A.) 1
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How many isomers of 1,3-heptadiene exist? a. 1 b. 2 c. 3 d. 4
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B.) 2
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How many isomers of 2,4-heptadiene exist? a. 1 b. 2 c. 3 d. 4
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D.) 4
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How many isomers of 1,3,5-heptatriene exist? a. 1 b. 2 c. 4 d. 8
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C.) 4
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What is the smallest trans cycloalkene that is stable at room temperature? a. (E) cyclohexene b. (E) cycloheptene c. (E) cyclooctene d. (E) cyclodecene
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C
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What types of units make up terpenes? a. isoprene b. propene c. vitamin A d. pentadiene
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Isoprene
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Which of the following is not true regarding alkenes? a. alkenes are non polar b. alkenes burn in air to give H2O and CO2 c. alkenes are highly miscible with water d. the strongest intermolecular force between alkene molecules is the van der Waals interaction
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C.) Alkenes are highly miscible with water
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Which of the following compounds is most reactive (least stable)? a. (Z)-cycloheptene b. (E)-cycloheptene c. (Z)-cyclooctene d. (E)-cyclooctene
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B.) (E)-cycloheptene
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Which of the following concepts explains why tertiary carbocations are more stable than primary and secondary carbocations? a. electronegativity b. resonance c. hyperconjugation d. the octet rule
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C.) Hyperconjugation
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What type of orbitals overlap to provide stability to the tert-butyl carbocation by hyperconjugation? a. 3° C 2p atomic orbital + 3° C sp2 atomic orbital b. 3° C 2p atomic orbital + methyl C?H ? molecular orbital c. 3° C sp2 atomic orbital + methyl C?H ? molecular orbital d. 3° C 2p atomic orbital + methyl C 2s atomic orbital
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b. 3° C 2p atomic orbital + methyl C?H ? molecular orbital
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Which of the following concepts explains Markovnikov's rule as applied to the addition of HBr to propene? a. the relative stability of carbocations b. the nucleophilicity of bromide anion c. the acidity of HBr d. the Aufbau principle
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a. the relative stability of carbocations
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What is the correct order of stability of carbocations?
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4º > 3º > 2º > 1º
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T/F? The reagent H2O; H2SO4 follows Markovnikov's rule and also does rearrangement.
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True!
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T/F? The reagent BH3; H2O2 does NOT follow Markovnikov's rule and follows trans-addition.
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True!
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T/F? Addition of HBr reagent follows Markovnikov's rule.
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True!
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T/F? 1. Hg(OAc)2 2. NaBH4 follows Markovnikov's rule.
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True
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T/F? In Br2, H2O, Br is added to the less substituted carbon while OH is added to the more substituted carbon. OH follows trans-addition, while Br follows cis-addition.
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True
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What is the major product obtained upon addition of Br2 to (R)-4-tert-butylcyclohexene? a. (1R,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane b. (1S,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane c. (1S,2S,4R)-1,2-dibromo-4-tert-butylcyclohexane d. (1S,2S,4S)-1,2-dibromo-4-tert-butylcyclohexane
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c.) (1S,2S,4R)-1,2-dibromo-4-tert-butylcyclohexane
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T/F? 1. OsO4 2. NaHSO3 H2O adds 2 OH groups to the reactant. Follows cis-addition.
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True
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T/F? 1. O3 2. (CH3)2S breaks open a cycloalkene.
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True
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T/F? H2/Pt follows cis-addition.
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True
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What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a bromoalkane? a. carbocation b. carbanion c. radical d. cyclic bromonium ion
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A.) carbocation
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What type of reactive intermediate is formed in the reaction of an alkene with Br2 and water to give a bromohydrin? a. carbocation b. carbanion c. radical d. cyclic bromonium ion
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D.) cyclic bromonium ion
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What type of reactive intermediate is formed in the reaction of an alkene with aqueous acid to give an alcohol? a. carbocation b. carbanion c. radical d. carbene
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a.) Carbocation
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What type of reaction mechanism accounts for the reaction of an alkene with aqueous acid to give an alcohol? a. nucleophilic addition b. electrophilic addition c. radical addition d. elimination
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b.) Electrophilic addition
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What type of reaction mechanism accounts for the reaction of an alkene with HBr to give an alkyl bromide? a. nucleophilic addition b. electrophilic addition c. radical addition d. elimination
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B.) Electrophilic addition
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Which of the following reactions of alkenes is not stereospecific? a. bromination (treatment with Br2 in CHCl3) b. hydrogenation (treatment with H2/Pt) c. acid-catalyzed hydration (treatment with aqueous H2SO4) d. bromohydrin formation (treatment with Br2/H2O)
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C.) Acid-catalyzed hydration
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Which of the following reactions of alkenes is stereospecific? a. addition of HCl (treatment with HCl) b. hydrogenation (treatment with H2/Pt) c. addition of HBr (treatment with HBr) d. acid-catalyzed hydration (treatment with aqueous H2SO4)
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B.) Hydrogenation
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Which of the following reactions of alkenes takes place with anti stereospecificity? a. bishydroxylation (treatment with OsO4 followed by NaHSO3) b. hydrogenation (treatment with H2/Pt) c. addition of HBr (treatment with HBr) d. bromohydrin formation (treatment with Br2, H2O)
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D.) bromohydrin formation
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Which of the following reactions of alkenes takes place with syn stereospecificity? a. addition of bromine (treatment with Br2) b. hydrogenation (treatment with H2/Pt) c. addition of HBr (treatment with HBr) d. acid-catalyzed hydration (treatment with aqueous H2SO4)
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B.) Hydrogenation
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Approximately how long is a carbon-carbon triple bond of an alkyne? a. 110 pm b. 121 pm c. 135 pm d. 156 pm
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B.) 121 pm
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What is the approximate C?C?C bond angle in propyne? a. 90° b. 109° c. 120° d. 180°
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D.) 180º
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How many alkynes are there with the molecular formula C6H10? a. 4 b. 5 c. 6 d. 7
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D.) 7
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Which atomic orbitals overlap to form the carbon-carbon triple bond of an alkyne? a. 2s + 2s; sp + sp; 2p + 2p b. sp + sp; sp + sp; 2p + 2p c. sp + sp; 2p + 2p; 2p + 2p d. sp2 + sp2; sp + sp; 2p + 2p
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c
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Which atomic orbitals overlap to form the carbon-carbon single bond of 1-propyne? a. 2s + sp b. sp + sp2 c. sp + sp3 d. sp2 + sp3
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C
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What is the smallest cycloalkyne that is stable at room temperature? a. cyclohexyne b. cyclononyne c. cyclododecyne d. cycloeicosyne
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B.) cyclononyne
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What is the IUPAC name of the following compound? CH3CH2CH2?C?C?CH(CH3)2 a. 1-isopropyl-1-pentyne b. 2-methyl-3-heptyne c. 6-methyl-4-heptyne d. isopropyl propyl ethyne
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B.) 2-methyl-3-heptyne
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What is the IUPAC name of the following compound? (CH3)2CHCH2?C?C?CH(CH3)2 a. 2,6-dimethyl-3-heptyne b. 2,6-dimethyl-4-heptyne c. 1,1,5,5-tetramethyl-2-pentyne d. 4-nonyne
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A.) 2,6-dimethyl-3-heptyne
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Which of the following is the strongest acid? a. propane b. cyclopropane c. propene d. propyne
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D.) propyne
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Which of the following has the lowest pKa? a. butane b. 1-butene c. 1-butyne d. 2-butyne
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c.) 1-butyne
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What is the major organic product obtained from a reaction involving NaNH2; DMSO?
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A alkyne or a aldiene.
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Which sequence of reactions can be used to convert 1-pentene to 1-pentyne a. Treatment with HBr; followed by treatment with NaOH b. Treatment with Br2; followed by treatment with NaNH2 c. Treatment with Br2; followed by treatment with H2SO4 d. Treatment with Br2, H2O; followed by treatment with NaOH
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B.) Treatment with Br2; followed by treatment with NaNH2
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Which sequence of reactions can be used to convert (Z) 2-pentene to 2-pentyne a. Treatment with Br2; followed by treatment with NaNH2 b. Treatment with Br2, H2O; followed by treatment with NaOH c. Treatment with Br2; followed by treatment with H2SO4 d. Treatment with HBr; followed by treatment with NaOH
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A.) Treatment with Br2; followed by treatment with NaNH2
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What is the major organic product obtained from the following reaction with Br2; CH3COOH, LiBr as the reagent? CH3-C(triplebond)C-CH3 a. (E) 1,2-dibromobutene b. (Z) 1,2-dibromobutene c. (E) 2,3-dibromobutene d. (Z) 2,3-dibromobutene
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C.) (E) 2,3-dibromobutene
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What is the major organic product obtained from the following reaction? CH3-C(triple bond)C-CH3 a. 2,3-dibromobutane b. 2,2,3,3-tetrabromobutane c. 2,3-dibromobutene d. 2,2-dibromobutane
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B.) 2,2,3,3-tetrabromobutane
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T/F? Addition of HBr to a alkyne follows Markovnikov's rule.
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True
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What is the major organic product obtained from the following reaction? CH3CH2CH2CH2-C(triple bond)C-H 1. BH3 2. H2O2, NaOH a. 2-hexanone b. hexanal c. 2-hexanol d. cis-2-hexene
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B.) Hexanal -anal for ALL BH3 reactions (including (sia)2BH)
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What is the major organic product obtained from the reagents: 1. H2O 2. HgSO4; H2SO4
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Ketones (double bond O)
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What type of intermediate s formed in the Hg2? catalyzed hydration of an alkyne?? a. an alcohol b. an enol c. a 1,2-diene d. an epoxide
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B.) An enol
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What happens when H2/Pd is added to an alkyne?
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Triple bond is completely broken apart; also breaks other multi-bonds
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What happens when 2Na;NH3(l) is added to 2-butyne?
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Trans-2-butene
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What happens when 1. BH3 2. CH3COOH is added to a reactant?
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Cis addition of some kind
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What happens when H2;Lindlar catalyst is added to a reactant?
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Cis addition of some kind
question
What is the best choice of reagent(s) to perform: 2,2-dibromopropane --> 2-propyne? a. H2O; H2SO4 b. 1. 3 moles of NaNH2; 2. H3O+ c. KMnO4, NaOH, H2O d. Zn
answer
B
question
Which of the following reagents react with 2-butyne to form (Z)-2-butene 1. H2/Lindlar catalyst 2. (sia)2BH followed by CH3COOH 3. Na/NH3 a. only 1 b. only 2 c. only 3 d. only 1 and 2
answer
D.) Only 1 and 2
question
Which of the following reagents react with 2-butyne to form butane a. H2/Lindlar catalyst b. H2/Pd c. (sia)2BH followed by CH3COOH d. Na/NH3
answer
B.) H2/Pd
question
What is the correct assignment of the names of the following compounds? 1. CH3Cl 2. CH2Cl2 3. CHCl3 a. 1 = methyl chloride; 2 = chloroform; 3 = methylene chloride b. 1 = trichlor; 2 = chloroform; 3 = methylene chloride c. 1 = methyl chloride; 2 = methylene chloride; 3 = chloroform d. 1 = chloroform; 2 = methylene chloride; 3 = trichlor
answer
C
question
Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point)? a. chloromethane > chloroethane > 2-chloropropane > 2-chloro-2-methylpropane b. 2-chloro-2-methylpropane > 2-chloropropane > chloroethane > chloromethane c. chloroethane > chloromethane > 2-chloro-2-methylpropane > 2-chloropropane d. chloromethane > 2-chloro-2-methylpropane > 2-chloropropane > chloroethane
answer
B
question
Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point)? a. 2-fluoropropane > 2-chloropropane > 2-bromopropane > 2-iodopropane b. 2-chloropropane > 2-iodopropane > 2-fluoropropane > 2-bromopropane c. 2-iodopropane > 2-chloropropane > 2-fluoropropane > 2-bromopropane d. 2-iodopropane > 2-bromopropane > 2-chloropropane > 2-fluoropropane
answer
d.2-iodopropane > 2-bromopropane > 2-chloropropane > 2-fluoropropane
question
Which of the following has the list of compounds in the correct order of decreasing density (higher density > lower density)? a. CH2Cl2 > CH2Br2 > CH2I2 b. CH2Cl2 > CH2I2 > CH2Br2 c. CH2I2 > CH2Br2 > CH2Cl2 d. CH2I2 > CH2Cl2 > CH2Br2
answer
c. CH2I2 > CH2Br2 > CH2Cl2
question
Which of the following has the list of compounds in the correct order of decreasing polarity (more polar > less polar)? a. CCl4 > CHCl3 > CH2Cl2 b. CH2Cl2 > CHCl3 > CCl4 c. CCl4 > CH2Cl2 > CHCl3 d. CHCl3 > CCl4 > CH2Cl2
answer
b. CH2Cl2 > CHCl3 > CCl4
question
Which of the following has the list of compounds in the correct order of decreasing molecular polar (more polar > less polar)? a. CH3I > CH3Br > CH3Cl > CH3F b. CH3F > CH3Cl > CH3Br > CH3I c. CH3Cl > CH3F > CH3Br > CH3I d. CH3Cl > CH3I > CH3F > CH3Cl
answer
C.) CH3Cl>CH3F>CH3Br>CH3I
question
Which of the following bonds has the lowest bond dissociation enthalpy? a. C?H b. C?F c. C?Br d. C?I
answer
D.) C-I
question
Which of the following statements is not true? a. homolytic cleavage of a bond in a neutral molecule gives two radicals b. radicals have one or more unpaired electrons c. movement of single electrons is depicted using a "fishhook arrow" d. the C?F bond is the weakest bond between carbon atom and a halogen
answer
D.) C-F bond is the weakest bond between carbon and a halogen
question
Which halogen is most useful in the regioselective radical halogenation of alkenes?? a. fluorine b. chlorine c. bromine d. iodine
answer
C.) Bromine
question
What is the correct order of stability of the following radicals (more stable > less stable)? 1.) 1º 2.) 3º 3.) 2º
answer
2 > 3 > 1
question
What is the characteristic of a radical chain initiation step? a. radicals are formed b. substitution products are formed c. a radical reacts with a molecule to give a new radical and a new molecule d. two radicals combine to give a molecule
answer
A.) radicals are formed
question
What is the characteristic of a radical chain propagation step? a. radicals are formed b. byproducts are formed c. a radical reacts with a molecule to give a new radical and a new molecule d. two radicals combine to give a molecule
answer
C.) a radical reacts with a molecule to give a new radical and a new molecule
question
What is the characteristic of a radical chain termination step? a. radicals are formed b. substitution products are formed c. a radical reacts with a molecule to give a new radical and a new molecule d. two radicals combine to give a molecule
answer
D.) two radicals combine to give a molecule
question
What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide to give 3-bromo-1-propene? a. allylic carbocation b. allylic carbanion c. allylic radical d. cyclic bromonium ion
answer
C.) allylic radical
question
What type of reactive intermediate is formed upon irradiation of a solution of toluene (Ph-CH3) and bromine? a. benzylic carbocation b. benzylic carbanion c. benzylic radical d. cyclic bromonium ion
answer
C.) benzylic radical
question
Which of the following alkanes does not undergo monobromination to form a single bromoalkane as the major product? 1.) 1-methylcyclohexane 2.) cyclohexane 3.) 2-methylpropane 4.) pentane a. 1 b. 2 c. 3 d. 4
answer
D.) 4
question
Which of the following alkenes undergoes allylic bromination to form a single monobrominated product? 1.) Cyclohexene 2.) 2-methyl-2-butene 3.) 1-propene 4.) 2-propene
answer
1.) Cyclohexene
question
What is the major product formed upon radical bromination of (S) 3-methylhexane? a. (S) 3-bromo-3-methylhexane b. (R) 3-bromo-3-methylhexane c. a mixture of (R) and (S) 3-bromo-3-methylhexane d. (3R) 1-bromo-3-methylhexane
answer
c. a mixture of (R) and (S) 3-bromo-3-methylhexane
question
What is the geometry of the central carbon atom of a tert-butyl radical? a. tetrahedral b. trigonal planar c. trigonal pyramidal d. square planar
answer
B.) Trigonal planar
question
Which of the following statements is not true about the allyl radical a. the carbon-carbon bond lengths are identical b. the unpaired electron density is shared between carbons 1 and 2. c. it undergoes reaction with bromine to give a single product d. it is formed by abstraction of a hydrogen atom from the methyl group of propene
answer
B.) The unpaired electron density is shared between carbons 1 and 2
question
How many electrons does the allyl radical have in p orbitals a. 1 b. 2 c. 3 d. 4
answer
C.) 3
question
How many ?-bonding, non-bonding, and antibonding orbitals does the allyl radical possess? a. one bonding, one nonbonding, and one antibonding b. two bonding, no nonbonding, and no antibonding c. two bonding, one nonbonding, and no antibonding d. three bonding, no nonbonding, and no antibonding
answer
A.) one bonding, one nonbonding, and one antibonding
question
What type of orbitals overlap to provide stability to the tert-butyl radical by hyperconjugation? a. 3° C 2p atomic orbital + 3° C sp2 atomic orbital b. 3° C 2p atomic orbital + methyl C?H ? molecular orbital c. 3° C sp2 atomic orbital + methyl C?H ? molecular orbital d. 3° C 2p atomic orbital + methyl C 2s atomic orbital
answer
B
question
What type of orbital contains the unpaired electron of the tert-butyl radical? a. s b. p c. sp3 d. ?
answer
B.) p
question
Which of the following is an accurate statement of Hammond's postulate? a. the transition state of an exothermic reaction will resemble the starting materials (reactants) more than the product b. the transition state of an exothermic reaction will resemble the products more than the starting materials (reactants) c. the transition state of an endothermic reaction will resemble the starting materials (reactants) more than the product d. the difference in energy between the starting materials (reactants) and transition state controls the rate of a reaction
answer
A.) The transition state of an EXOTHERMIC reaction will resemble the starting materials (reactants) more than the product
question
Which of the following statements is not true regarding the halogenation of alkanes upon treatment with halogen and light? a. bromination is more selective for 3° positions than chlorination b. the reaction proceeds via a radical intermediate c. the reaction proceeds via a chain reaction d. this is a useful process for the formation of fluorides, chlorides, bromides and iodides
answer
D.) This is a useful process for the formation of fluorides, chlorides, bromides, and iodides
question
What type of reactive intermediate is formed in the reaction of propene with hydrogen bromide in the presence of peroxides to give 1-bromopropane? a. 1° radical b. 1° carbocation c. 1° radical d. 2° radical
answer
D
question
What is the major product obtained from the reaction of 2-methyl-2-butene with hydrogen bromide in the presence of peroxides? a. 2,3-dibromo-2-methylbutane b. 2-bromo-3-methylbutane c. 2-bromo-2-methylbutane d. (E)-1-bromo-2-methyl-2-butene
answer
B.) 2-bromo-3-methylbutane
question
Which of the following statements is not true? a. Bromine radicals add to the least substituted end of a carbon-carbon double bond of an alkene. b. The major anti-Markovnikov product obtained upon addition of HBr to alkenes in the presence of a peroxide is formed in a radical termination step. c. Two radicals combine in radical termination steps. d. Alkoxy radicals remove a hydrogen atom from HBr to give an alcohol and a bromine atom.
answer
B.) The major anti-Markovnikov product obtained upon addition of HBr to alkenes in the presence of a peroxide is formed in a radical termination step.
question
Which of the following compounds is most susceptible to autooxidation? a. propene b. 1,3-butadiene c. 1,4-pentadiene d. 1,5-hexadiene
answer
C.) 1,4 - pentadiene
question
What is the reactive intermediate in the autooxidation of cyclohexene? a. an allylic radical b. a 2° carbocation c. a carbocation d. a diene
answer
A.) an allylic radical
question
What are the major products formed upon treatment of (E) 3-methyl-2-hexene with HBr in the presence of peroxides? 1. (S,S) 2-bromo-3-methylhexane 2. (S,R) 2-bromo-2-methylhexane 3. (R,S) 2-bromo-2-methylhexane 4. (R,R) 2-bromo-2-methylhexane a. only 1 and 2 b. only 1 and 4 c. only 2 and 3 d. a mixture of 1, 2, 3, and 4
answer
D.) A mixture of 1, 2, 3, 4
question
What are the major products formed upon treatment of (E) 3-methyl-2-hexene with HBr in the absence of peroxides? 1. (S) 3-bromo-3-methylhexane 2. (R) 3-bromo-2-methylhexane 3. 2-bromo-3-methylhexane a. only 1 b. only 2 c. a mixture of 1 and 2 d. only 3
answer
D.) Only 3
question
Which of the following accounts for the anti-Markovnikov regiochemistry of the reaction of an alkene with HBr in the presence of peroxides? a. the alkene reacts with HBr to give a carbocation b. the alkene reacts with a bromine atom to give a radical c. the alkene reacts with a hydrogen atom to give a radical d. the alkene reacts with peroxide to five an allylic radical
answer
B.) The alkene reacts with a bromine atom to a give a radical
question
Which of the following reactions corresponds to a substitution? a. propene ? 1,2-dibromopropane b. 1-iodopropane ? propene c. propene ? propane d. 1-iodopropane ? 1-bromopropane
answer
d. 1-iodopropane ? 1-bromopropane
question
Which of the following reactions corresponds to a substitution? a. tert-butanol ? tert-butyl chloride b. tert-butanol ? 2-methylpropene c. 3,3-dimethyl-2-butanol ? 2,3-dimethyl-2-butene d. cyclohexene ? 1,2-dichlorocyclohexane
answer
a. tert-butanol ? tert-butyl chloride
question
Which of the following statements related to SN1 reactions is not true? a. The heterolysis of a bond between atoms which do not bear formal charges always produces a cation and an anion b. The charged carbon atom of a carbocation has a complete octet of valence shell electrons c. Carbocations are Lewis acids d. Nucleophiles seek centers of low electron density
answer
b. The charged carbon atom of a carbocation has a complete octet of valence shell electrons
question
Which of the following statements related to SN1 reactions is not true? a. The SN1 reaction can be described as a heterolytic bond cleavage followed by nucleophilic attack b. Carbocations are electrophilic c. The charged carbon atom of a carbocation has an unfilled valence shell d. Nucleophiles are Lewis acids
answer
d. Nucleophiles are Lewis acids
question
What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an SN1 mechanism? a. Rate = k [t-BuBr] b. Rate = k [t-BuBr][H2O] c. Rate = k [H2O] d. Rate = k [t-BuBr]2
answer
a. Rate = k [t-BuBr]
question
What is the equation for the rate of formation of 1-iodobutane from the reaction of 1-chlorobutane (BuCl) with NaI by an SN2 mechanism? a. Rate = k [BuCl] b. Rate = k [BuCl][NaI] c. Rate = k [NaI] d. Rate = k [BuCl]2
answer
b. Rate = k [BuCl][NaI]
question
What is the equation for the rate of formation of 2-methoxypropane, (CH3CH(OCH3)CH3, from the reaction of 2-bromopropane (i-PrBr) with sodium methoxide (NaOCH3)? a. Rate = k [i-PrBr] b. Rate = k [i-PrBr]2 c. Rate = k [NaOCH3] d. Rate = k [i-PrBr][NaOCH3]
answer
d. Rate = k [i-PrBr][NaOCH3]
question
What is the equation for the rate of formation of 2-methoxypropane, CH3CH(OCH3)CH3, from the reaction of 2-bromopropane (i-PrBr) with methanol? a. Rate = k [i-PrBr] b. Rate = k [i-PrBr]2 c. Rate = k [CH3OH] d. Rate = k [i-PrBr][CH3OH]
answer
a. Rate = k [i-PrBr]
question
The reaction of methyl iodide with sodium azide, NaN3, proceeds by an SN2 mechanism. What is the effect of doubling the concentration of NaN3 on the rate of the reaction? a. the rate remains the same b. the rate decreases by a factor of 2 c. the rate increases by a factor of 2 d. the rate increases by a factor of 4
answer
c. the rate increases by a factor of 2
question
The reaction of 1-bromopropane with sodium iodide gives 1-iodopropane. What is the effect of doubling the concentration of NaI on the rate of the reaction? a. the rate remains the same b. the rate decreases by a factor of 2 c. the rate increases by a factor of 2 d. the rate increases by a factor of 4
answer
c. the rate increases by a factor of 2
question
The reaction of tert-butyl bromide, (CH3)3CBr, with methanol in an inert solvent proceeds by an SN1 mechanism to give tert-butyl methyl ether, (CH3)3COCH3. What is the effect of doubling the concentration of methanol on the rate of the reaction? a. the rate remains the same b. the rate decreases by a factor of 2 c. the rate increases by a factor of 2 d. the rate increases by a factor of 4
answer
A
question
The reaction of tert-butyl chloride, (CH3)3CCl, with water in an inert solvent gives tert-butyl alcohol, (CH3)3COH. What is the effect of doubling the concentration of water on the rate of the reaction? a. the rate remains the same b. the rate decreases by a factor of 2 c. the rate increases by a factor of 2 d. the rate increases by a factor of 4
answer
a. the rate remains the same
question
Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium azide, NaN3? a. 1-fluorohexane b. 1-chlorohexane c. 1-bromohexane d. 1-iodohexane
answer
d. 1-iodohexane
question
Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium cyanide, NaCN? a. methyl iodide b. ethyl iodide c. 2-iodopropane d. tert-butyl iodide
answer
a. methyl iodide
question
Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium methylthiolate, NaSMe? a. methyl iodide b. ethyl iodide c. 2-bromopropane d. tert-butyl chloride
answer
a. methyl iodide
question
Which of the following alkyl halides undergoes the fastest solvolysis reaction with formic acid, HCOOH? a. tert-butyl fluoride b. tert-butyl chloride c. tert-butyl bromide d. tert-butyl iodide
answer
d. tert-butyl iodide
question
Which of the following alkyl halides undergoes the fastest solvolysis reaction with methanol, CH3OH? a. methyl chloride b. ethyl chloride c. 2-chloropropane d. tert-butyl chloride
answer
d. tert-butyl chloride
question
Which of the following alkyl halides undergoes the fastest solvolysis reaction with ethanol, CH3CH2OH? a. methyl fluoride b. ethyl bromide c. 2-chloropropane d. tert-butyl bromide
answer
d. tert-butyl bromide
question
Which of the following is best set of conditions for the preparation of tert-butanol? a. tert-butyl fluoride in water b. tert-butyl bromide in water c. tert-butyl fluoride and NaOH in DMSO d. tert-butyl bromide and NaOH in DMSO
answer
b. tert-butyl bromide in water
question
Which of the following is the best set of conditions for the preparation of tert-butyl methyl ether? a. tert-butyl fluoride and NaOCH3 in CH3OH b. methanol and sodium tert-butoxide in tert-butanol c. fluoromethane and sodium tert-butoxide in tert-butanol d. tert-butyl bromide and CH3OH
answer
d. tert-butyl bromide and CH3OH
question
What is the major product formed upon treatment of (R) 1-bromo-4-methylhexane with sodium cyanide? a. (R) 1-cyano-4-methylhexane b. (S) 1-cyano-4-methylhexane c. (R) 4-methyl-1-hexene d. (S) 4-methyl-1-hexene
answer
a. (R) 1-cyano-4-methylhexane
question
What is the major product formed upon treatment of (R) 2-bromohexane with sodium cyanide? a. (R) 2-cyanohexane b. (S) 2-cyanohexane c. 1-hexene d. 2-hexene
answer
(S) 2-cyanohexane
question
In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN3, proceed the fastest? a. acetic acid b. ethanol c. water d. acetonitrile
answer
d. acetonitrile
question
Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide? a. dimethylsulfoxide b. water c. hexane d. toluene, PhCH3
answer
a. dimethylsulfoxide
question
Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide? a. water b. N,N-dimethylformamide c. hexane d. toluene, PhCH3
answer
b. N,N-dimethylformamide
question
Which of the following anions is the most nucleophilic in polar protic solvents? a. F? b. Cl? c. Br? d. I?
answer
d. I?
question
Which of the following anions is the most nucleophilic in polar aprotic solvents? a. F? b. Cl? c. Br? d. I?
answer
a. F?
question
Which of the following compounds is the most nucleophilic in polar protic solvents? a. H2O b. NH3 c. H2S d. PH3
answer
d. PH3
question
Which of the following is the most nucleophilic? a. sodium ethoxide b. acetic acid c. methanol d. water
answer
a. sodium ethoxide
question
Which of the following anions is the best leaving group in an SN1 reaction? a. F? b. HO? c. NH2? d. Cl?
answer
d. Cl?
question
Which of the following is the best leaving group in an SN2 reaction? a. F? b. H3C? c. CH3O2SO? d. HO?
answer
c. CH3O2SO?
question
Which of the following statements is true regarding the reactivity of 1 and 2 with potassium tert-butoxide? a. 1 reacts faster than 2 b. 1 and 2 give different dehydrochlorinated products c. 2 reacts by elimination whereas 1 reacts by substitution d. 1 reacts by elimination whereas 2 reacts by substitution
answer
a. 1 reacts faster than 2
question
Which of the following statements is not true regarding the SN2 reaction of (R)-2-bromobutane with sodium cyanide? a. the reaction proceeds with inversion of configuration b. the rate is proportional to the concentration of sodium cyanide c. the rate is proportional to the concentration of (R)-2-bromobutane d. the rate of the reaction is independent of the identity of the solvent
answer
d. the rate of the reaction is independent of the identity of the solvent
question
Which of the following statements is true regarding the reaction of tert-butyl bromide with water? a. the rate is proportional to the concentration of tert-butyl bromide b. the rate is proportional to the concentration of water c. the rate is independent of the identity of the solvent d. the rate of the reaction is independent of the temperature
answer
a. the rate is proportional to the concentration of tert-butyl bromide
question
Which of the following is not a characteristic of SN2 reactions? a. the electrophilic carbon undergoes inversion of stereochemistry b. the rate is proportional to the concentration of substrate c. the rate is proportional to the concentration of nucleophile d. the rate is independent of the solvent
answer
d. the rate is independent of the solvent
question
Which of the following is not a characteristic of SN1 reactions? a. the electrophilic carbon undergoes inversion of stereochemistry b. the rate is proportional to the concentration of substrate c. the reaction proceeds faster in a more polar solvent d. the rate is independent of the concentration of nucleophile
answer
a. the electrophilic carbon undergoes inversion of stereochemistry
question
What is the role of tetrabutylammonium chloride as a phase transfer catalyst in the reaction of 1-chlorooctane and sodium cyanide in a mixture of water and CH2Cl2? a. it transfers 1-chlorooctane into the aqueous phase b. it transfers cyanide anion into the organic phase c. it makes water and dichloromethane miscible d. it transfers the sodium cation into the organic phase
answer
b. it transfers cyanide anion into the organic phase
question
Which of the following statements is not true regarding SN2 reactions? a. A carbocation intermediate is formed. b. The mechanism has only one step. c. Aprotic solvents are good choices for SN1 reactions. d. The stereochemical outcome is inversion at the carbon bearing the leaving group.
answer
a. A carbocation intermediate is formed.
question
Which of the following statements is not true regarding SN1 reactions? a. A carbocation intermediate is formed. b. The mechanism has only one step. c. Polar, protic solvents are good choices for SN1 reactions. d. The stereochemical outcome is racemization at the carbon bearing the leaving group.
answer
b. The mechanism has only one step.
question
How many steps does SN1 occur in?
answer
2 steps
question
How many steps does SN2 occur in?
answer
1 step
question
How many steps does an E2 reaction occur in?
answer
1 step
question
How many steps does an E1 reaction occur in?
answer
2 steps
question
Which of the following sets consists of only polar aprotic solvents? a. water, hexane, methanol b. acetic acid, DMF, toluene c. DMSO, ethanol, acetonitrile d. DMF, acetonitrile, DMSO
answer
d. DMF, acetonitrile, DMSO
question
Which of the following sets consists of only polar protic solvents? a. water, DMF, DMSO b. acetic acid, methanol, water c. DMSO, ethanol, acetonitrile d. DMF, acetonitrile, DMSO
answer
b. acetic acid, methanol, water
question
Which of the following most favors elimination rather substitution in a reaction with 2-bromopropane? a. sodium methoxide b. sodium ethoxide c. sodium isoproxide d. sodium tert-butoxide
answer
d. sodium tert-butoxide
question
Which of the following most favors elimination rather substitution in a reaction with sodium methoxide? a. bromomethane b. bromoethane c. 1-bromopropane d. 2-bromopropane
answer
d. 2-bromopropane
question
What is the approximate C?O?H bond angle of an alcohol? a. 90° b. 109.5° c. 120° d. 180°
answer
b. 109.5°
question
What is the approximate C?C?O bond angle of ethanol? a. 90° b. 109.5° c. 120° d. 180°
answer
b. 109.5°
question
Know how to distinguish primary and secondary alcohols.
answer
C:
question
Which of the following has the highest boiling point? a. pentane b. methyl propyl ether c. diethyl ether d. 1-butanol
answer
d. 1-butanol
question
Which of the following has the highest boiling point? a. 1-butanol b. 2-butanol c. tert-butyl alcohol d. 1,4-butanediol
answer
d. 1,4-butanediol
question
What is the approximate pKa value of ethanol? a. ?5 b. 5 c. 16 d. 25
answer
c. 16
question
Which of the following best describes the reaction of sodium metal with methanol to give hydrogen and sodium methoxide? a. Lewis acid-base b. Brønsted-Lowry acid-base c. electrophile-nucleophile d. oxidation-reduction
answer
d. oxidation-reduction
question
What is the major organic product obtained from the reaction of 1-butanol with aqueous HBr at reflux? a. 1-bromobutane b. 2-bromobutane c. 2-bromo-1-butanol d. 1-butene
answer
a. 1-bromobutane
question
What is the major organic product obtained from the reaction of 2,2-dimethyl-1-propanol aqueous HBr at reflux? a. 1-bromo-2,2-dimethylpropane b. 1-bromo-2-methylbutane c. 2-bromo-2-methylbutane d. 3-bromo-2-methylbutane
answer
c. 2-bromo-2-methylbutane
question
Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide? a. methanol b. ethanol c. 2-propanol d. 2-methyl-2-propanol
answer
d. 2-methyl-2-propanol
question
What type of reactive intermediate is formed in the reaction of 2-methyl-2-hexanol with HBr to give 2-bromo-2-methylhexane? a. an alkoxide b. a tertiary cation c. a tertiary radical d. a tertiary anion
answer
b. a tertiary cation
question
What is the major organic product obtained upon heating a mixture of 2-methylcyclopentanol and 85% H3PO4? a. 1-methylcyclopentene b. 3-methylcyclopentene c. 4-methylcyclopentene d. methylenecyclopentene
answer
a. 1-methylcyclopentene
question
What is the major organic product obtained upon heating a mixture of 3,3-dimethyl-2-butanol, (CH3)3CCH(OH)CH3, with sulfuric acid? a. 3,3-dimethyl-1-butene b. 2,3-dimethyl-1-butene c. 2,3-dimethyl-2-butene d. tert-butyl alcohol
answer
c. 2,3-dimethyl-2-butene
question
What is the major organic product obtained upon heating a mixture of 2-butanol and 85% H3PO4? a. 1-butene b. cis-2-butene c. trans-2-butene d. 2-methylpropene (isobutylene)
answer
c. trans-2-butene
question
Which of the following alcohols undergoes the most rapid dehydration upon treatment with H2SO4 to give an alkene? a. methanol b. ethanol c. 2-propanol d. 2-methyl-2-propanol
answer
d. 2-methyl-2-propanol
question
In a reaction with CrO3, a primary alcohol becomes a ___________ ______.
answer
carboxylic acid
question
In a reaction with CrO3, a secondary alcohol becomes a _________.
answer
ketone
question
In a reaction with PCC, a primary alcohol becomes __________.
answer
aldehyde
question
In a reaction with PCC, a secondary alcohol becomes a __________.
answer
ketone
question
What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with HCl to give tert-butyl chloride? a. tert-butyl radical b. tert-butyl anion c. tert-butyl cation d. tert-butoxide
answer
c. tert-butyl cation
question
What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with H2SO4 to give methylpropene? a. tert-butyl cation b. tert-butyl anion c. tert-butyl radical d. tert-butoxide
answer
a. tert-butyl cation
question
What defines an ether?
answer
An oxygen bonded to two other carbons
question
What defines an epoxide?
answer
"Just the triangle thingy, it usually has an R group attached it. You usually yeah Idk" - Maryam
question
Triangle = _________
answer
oxirane
question
Square = _________
answer
oxetane
question
Pentagon = __________
answer
oxolane
question
Hexagon = __________
answer
oxane
question
Thiols have ______.
answer
-SH
question
Which of the following statements are true? 1. ethanol is more soluble in water than dimethyl ether 2. ethanol has a higher boiling point than dimethyl ether 3. ethanol has the same molecular weight as dimethyl ether a. only 1 b. only 1 and 2 c. only 1 and 3 d. 1, 2 and 3
answer
d. 1, 2 and 3
question
What is the IUPAC name of the following compound? a. ethyl isopropyl thiol b. 2-ethylsulfanylpropane c. ethyl isopropyl disulfide d. isopropylsufanylethane
answer
b. 2-ethylsulfanylpropane
question
Which of the following reactions provides anisole (PhOCH3) in a high yield? a. phenol + sodium methoxide b. bromobenzene + bromomethane c. sodium phenoxide (PhONa) + bromomethane d. bromobenzene + sodium methoxide
answer
c. sodium phenoxide (PhONa) + bromomethane
question
Which of the following reactions provides tert-butyl methyl ether in a high yield? a. potassium tert-butoxide + iodomethane b. sodium methoxide + tert-butyl bromide c. methanol + tert-butyl alcohol in the presence of KOH d. iodomethane + tert-butyl bromide in the presence of KOH
answer
a. potassium tert-butoxide + iodomethane
question
Which of the following ethers cannot be prepared by a Williamson ether synthesis? a. tert-butyl phenyl ether b. isopropyl methyl ether c. anisole d. tert-butyl methyl ether
answer
a. tert-butyl phenyl ether
question
What type of reactive intermediate is formed in the reaction of tert-butyl methyl ether with HBr to give tert-butyl bromide? a. tert-butyl anion b. tert-butoxide c. tert-butyl radical d. tert-butyl cation
answer
d. tert-butyl cation
question
What type of mechanism accounts for the cleavage of dibutyl ether upon treatment with HBr to give two moles of 1-bromobutane? a. SN1 b. SN2 c. E1 d. E2
answer
b. SN2
question
What type of mechanism accounts for the cleavage of tert-butyl methyl ether upon treatment with HBr? a. SN1 b. SN2 c. E1 d. E2
answer
a. SN1
question
What are the major products obtained upon treatment of anisole, PhOCH3, with excess HBr? a. phenol and methanol b. bromobenzene and bromomethane c. phenol and bromomethane d. bromobenzene and methanol
answer
c. phenol and bromomethane
question
What are the major products obtained upon treatment of tert-butyl methyl ether with excess HBr? a. tert-butyl alcohol and methanol b. tert-butyl bromide and methanol c. tert-butyl alcohol and bromomethane d. tert-butyl bromide and bromomethane
answer
d. tert-butyl bromide and bromomethane
question
What type of reactive intermediate is formed in the reaction of methyl propene with methanol in the presence of an acid catalyst to give methyl tert-butyl ether (MTBE)? a. tert-butyl cation b. tert-butyl radical c. tert-butyl anion d. tert-butoxide
answer
a. tert-butyl cation
question
Which of the following general structures can be made by sequential reaction of epichlorohydrin with appropriate nucleophiles?
answer
C.) 3
