Organic Chemistry 1 Lab: Part 2

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c) Fatty Acids
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To which class of organic compounds does trimyristin belong? a) Ester b) Ethers c) Fatty Acids d) Glycerol e) Ketones
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d) Hydrolysis
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How is trimyristin converted to myristic acid? a) Column Chromatography b) Recrystallization c) Simple Distillation d) Hydrolysis e) Fractional Distillation
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e) 3
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How many moles of myristic acid are produced by 1 mole of trymyristin? a) 0 b) 1 c) 1.5 d) 2 e) 3
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a) Mixed Melting Point
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Which concept is helpful in determining the conversion of trimyristin to myristic acid? a) Mixed Melting Point b) Hydrolysis c) Refluxing d) Column Chromatography e) B and C
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a) Trimyristin was not hydrolyzed to myristic acid
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Suppose a student follows the procedure to hydrolyze trimyristin to myristic acid and wants to confirm if the reaction works. During the melting point measurement, a 50:50 (by weight) mixture of the starting trimyristin and the product myrsitic acid is found to have the same melting point as that of trimyristin, which statement is true? a) Trimyristin was not hydrolyzed to myristic acid b) Myristic acid was not hydrolyzed to trimyristin c) Trimyristin was hydrolyzed to myristic acid d) Myristic acid was not hydrolyzed to trimyristin e) It is hard to tell about the reaction course
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c) It is synthesized via SN1 mechanism
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Which of the following is true about the synthesis of tert-butyl chloride? a) It is synthesized from 1-butanol b) It is synthesized via SN2 mechanism c) It is synthesized via SN1 mechanism d) It is synthesized via both SN1 and SN2 mechanism e) It is synthesized from a secoondary alcohol
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d) 2-chloro-2-methylethane
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Which alkyl halide shall give a postive result upon reacting with AgNO3? a) Chlorobutane b) 2-chlorobutane c) 1-chloro-2-methylpropane d) 2-chloro-2-methylethane e)2,3-dimethylbutane
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a) Primary
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Which types of alkyl halides shall readily react with NaI? a) Primary b) Secondary c) Teritary d) b and c e) a, b, and c
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e) 2-methylpropene
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What is the side reaction during the synthesis of ter-butyl chloride via SN1 reaction? a) 2-chloro-2-methylethane b) Chlorobutane c) 2-chlorobutane d) butene e) 2-methylpropene
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d) Avoiding over heating
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How do you avoid the formation of the side product when synthesizing ter-butyl chloride via SN1 reaction? a) Drying the aqueous layer b) Neutralizing the organic layer c) Using silver nitrate d) Avoiding over heating e) b and c f) all except a
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a) Alkene
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To which class of organic compounds does the side products of SN2 reaction belong to? a) Alkene b) Alkyne c) Alkane d) Quaternary Salt e) Alkyl Halide
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e) Quarternary ammonium salt
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In an Sn2 mechanism, the reaction of a tertiary amine with an alkyl halide will produce_________________? a) Primary halide b) Secondary halide c) Primary ammonium salt d) Tertiary ammonium salt e) Quarternary ammonium salt
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c) Gas chromatography
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Which technique can be used to identify the relative amounts of each products when an alkene is synthesized from an alcohol. a) Simple distillation b) Column chromatography c) Gas chromatography d) Fractional Distillation e) Recrystalliztion
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c) Water
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Alcohols can be protonated to form a good leaving group called _________________? a) Ester b) Diol c) Water d) Acid e) Hydroxide
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c) E1
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In converting alcohols o alkenes, which mechanism is utilize? a) SN1 b) SN2 c) E1 d) E2 e) c and d
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b) He or N2 gas
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Which of the following is considered a mobile phase in gas chromatography experiment? a) Celite packed in a stainless steel column b) He or N2 gas c) Solid material of high melting point packed in capillary column d) Solid alumina e) All except B
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a) The most volatile compound has a lower retention time
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What is true about retention time in a gas chromatography experiment? a) The most volatile compound has a lower retention time b) The least volatile compound has a lower retention time c) The major alkene has a lower retention time d) The minor alkene has a higher retention time e) A and D can be true
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e) Both c and d
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Which compounds can be used to identify ethene? a) Chromic acid b) Acetone c) Bromine d) Potassium permanganate e) Both c and d
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e) A or C
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Which reagent will identify 1-butanol? a) CrO3/ H2SO4 b) Br2 c) Jones reagent d) 2,4-DNP e) A or C
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c) cyclohexene
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Which of the following compounds will convert a red solution of bromide to colorless? a) 1-methyl-1-cyclohex-1-ol b) Cyclohexone c) Cyclohexene d) Cyclohexoic acid e) Cyclohexane
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e) Imines
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Carbonyl is a chemical group that in acidic media combine with amine creating compounds known as _________ a) Alkenes b) Ketones and aldehydes c) Alcohols d) Esters e) Imines
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d) Sodium trichloroacetate
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Which of the following reacts with 1,5-cyclooctadiene to produce the tricyclic desired product? a) Tetrachloromethylene b) Propionaldehyde c) Tetrachloroethylene d) Sodium trichloroacetate e) None of the above
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d) They are generated in protic solvent
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Which is not true about carbenes? a) They are reactive intermediates b) They act as electrophiles c) They act as nucleophiles d) They are generated in protic solvent e) All are true
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a) Steam distillation
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How do you separate the desired product from the solvents in the experiment that focused on producing a tertachlorotricyclo product? a) Steam distillation b) Simple distillation c) Fractional distillation d) Recrystallization e) Vacuum evaporation
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c) Using aprotic solvents
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How do you avoid the potential side reaction in the reaction that focused on producing a tertachlorotricyclo product? a) Steam distillation b) Using protic solvents c) Using aprotic solvents d) Using carebenes e) Refluxing
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Silica gel (polar)
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In Thin Layer Chromotography (TLC), what is the stationary phase?
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It moves the sample
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What is the mobile phase?
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100%
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What is the enantiomer excess for pure R or S compounds?
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0%
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What is the ee% for a racemic mixture?
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Short (2-3) and high
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What is the melting point range of pure substance?
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Broad and lower
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What is the range of a mixed melting point?
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Siloxanes (non-volatile)
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In gas chromatography, what is the stationary phase?
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Aprotic solvent
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In a Grignard reaction, what type of solvent should be used?
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Difference in BP is greater than 11C
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When is simple distillation used?
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Difference in BP is less than 11C
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When is fractional distillation used?
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(actual/ theoretical) x 100
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How do you calculate percent yield?
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Uses the BP of the solvent that you want to distillate. It is for temperature sensitive materials like natural aromatic compounds.
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Steam distillation
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A 50:50 mixture of both compound is made. If the MP if lower and broad; hydrolysis was successful.
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What is mixed melting point?
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(distance travelled by compound/ distance travelled by solvent)
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How do you calculate Rf?
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It is based on intermolecular forces
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What does extraction depends on?
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Compounds made up of 2 or more 5 carbon units (isoprene)
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What are terpenes?
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([a] observed / [a] pure) x 100%
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%ee =
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n^t + 0.00045 (t- 20C)
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Refractive index correction
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To test for tertiary halides
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What is the silver nitrate test for?
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It tests for primary halides.
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What does the sodium iodide test test?
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Elimination reactions
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What does heat induce?
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Unimolecular, 1 step, polar protic solvent
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What are SN1 reaction?
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bimolecular, 2 step, polar aprotic solvent
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What are SN2 reaction?
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triethylamine (TEA)
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Which reacts faster in an SN2 reaction: ethyldiisoproprlamine (EDA) and triethylamine (TEA)?
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If the column is polar, the non-polar component leaves first, the polar component interacts
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Gas chromotography
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Potassium permanganate (produce muddy precipitate); bromine forms colorless solution
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In a qualitative test, how is the presence of alkenes tested?
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Jones reagent (chromic acid-sulfuric acid)- changed to blue/green precipitate
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In a qualitative test, how is the presence of alcohols tested?
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2,4-dinotrophenylhydrazine (2,4-DNP)- forms yellow or orange precipitate
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In a qualitative test, how is the presence of carbonyls tested?

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