O Chem Final

What is the major product formed upon treatment of (R) 1-bromo-4-methylhexane with sodium cyanide?
(R) 1-cyano-4-methylhexane
(S) 1-cyano-4-methylhexane
(R) 4-methyl-1-hexene
(S) 4-methyl-1-hexene
(R) 1-cyano-4-methylhexane
Which of the following statements is not true regarding SN2 reactions?
A carbocation intermediate is formed.
The mechanism has only one step.
Aprotic solvents are good choices for SN1 reactions.
The stereochemical outcome is inversion at the carbon bearing the leaving group.
A carbocation intermediate is formed.
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?
Stays the same
Which of the following sets consists of only polar protic solvents?
water, DMF, DMSO
acetic acid, methanol, water
DMSO, ethanol, acetonitrile
DMF, acetonitrile, DMSO
acetic acid, methanol, water
Which of the following statements is not true regarding SN1 reactions?
A carbocation intermediate is formed.
The mechanism has only one step.
Polar, protic solvents are good choices for SN1 reactions.
The stereochemical outcome is racemization at the carbon bearing the leaving group.
The mechanism has only one step.
Which of the following has the highest boiling point?
pentane
methyl propyl ether
diethyl ether
1-butanol
1-butanol
Which of the following is not a characteristic of SN2 reactions?
the electrophilic carbon undergoes inversion of stereochemistry
the rate is proportional to the concentration of substrate
the rate is proportional to the concentration of nucleophile
the rate is independent of the solvent
the rate is independent of the solvent
Which of the following anions is the best leaving group in an SN1 reaction?
F-
HO-
NH2-
Cl-
Cl-
What is the major organic product obtained from the reaction of 2,2-dimethyl-1-propanol aqueous HBr at reflux?
1-bromo-2,2-dimethylpropane
1-bromo-2-methylbutane
2-bromo-2-methylbutane
3-bromo-2-methylbutane
The correct product is not listed.
2-bromo-2-methylbutane
What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with HCl to give tert-butyl chloride?
tert-butyl radical
tert-butyl anion
tert-butyl cation
tert-butoxide
tert-butyl cation
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)?
tert-butyl cation
tert-butyl radical
tert-butyl anion
tert-butoxide
tert-butyl cation
Which of the following ethers cannot be prepared by a Williamson ether synthesis?
tert-butyl phenyl ether
isopropyl methyl ether
anisole
tert-butyl methyl ether
tert-butyl phenyl ether
What is the major organic product obtained from the reaction of 2,2-dimethyl-1-propanol aqueous HBr at reflux?
1-bromo-2,2-dimethylpropane
1-bromo-2-methylbutane
2-bromo-2-methylbutane
3-bromo-2-methylbutane
2-bromo-2-methylbutane
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 dimethylether
only 1
only 1 and 2
only 1 and 3
1, 2 and 3

1, 2, and 3
What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with H2SO4 to give methylpropene?
tert-butyl cation
tert-butyl anion
tert-butyl radical
tert-butoxide
tert-butyl cation
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