Question 1

Which of the following reagents would convert an epoxide to a trans-1,2-diol under basic conditions?

Accepted Answer

$$\mathrm{NaOH,\ H_2O}$$

Question 2

What is the major product when 2-methylcyclopentanol is treated with concentrated $$\mathrm{H_2SO_4}$$?

Accepted Answer

1,2-dimethylcyclopentene

Question 3

Which of the following best describes the mechanism for the acid-catalyzed conversion of hex-5-en-1-ol to a six-membered cyclic ether?

Accepted Answer

Intramolecular SN1 reaction after alcohol protonation

Question 4

Which of the following is the correct order of increasing acidity (lower to higher pKa) for the following functional groups: alcohol, alkyne, alkane?

Accepted Answer

alkane \u003c alkyne \u003c alcohol

Question 5

In the Williamson ether synthesis, which combination of reactants would maximize the yield of ethyl methyl ether?

Accepted Answer

Reacting methyl bromide with sodium ethoxide

Question 6

Which of the following best describes the stereochemical outcome when an epoxide is opened by a nucleophile under basic conditions?

Accepted Answer

The nucleophile attacks the less substituted carbon with inversion of configuration

Question 7

Which of the following reagents would convert 1-bromopentane to pentan-1-ol in a single step?

Accepted Answer

$$\mathrm{NaOH}$$

Question 8

Which of the following is the correct product when 1-bromo-2-methylpropane is treated with sodium methoxide?

Accepted Answer

1-methoxy-2-methylpropane

Question 9

Which of the following best describes the product(s) when 1,2-dimethylcyclohexene is treated with $$\mathrm{Br_2$} in $$water?

Accepted Answer

A racemic mixture of bromohydrins

Question 10

Which of the following sequences would convert cyclohexyl bromide to cyclohexylacetylene?

Accepted Answer

1. $$\mathrm{$$NaNH_2$$}$$, 2. $$\mathrm{CH_3I}$$, 3. $$\mathrm{$$NaNH_2$$}$$

Question 11

Which of the following is the correct product when 1-phenyl-2-propanol is treated with $$\mathrm{NaOH}$$?

Accepted Answer

1-phenyl-2-propanone

Question 12

Which of the following is the correct pKa order for the following acids: water, alcohol, carboxylic acid?

Accepted Answer

carboxylic acid \u003c water \u003c alcohol

Question 13

Which of the following best describes the product when cyclohexanol is treated with HCl?

Accepted Answer

A racemic mixture of cyclohexyl chloride

Question 14

Which of the following is the correct mechanism for the conversion of an alcohol to an alkene using $$\mathrm{H_2SO_4}$$?

Accepted Answer

E1 elimination

Question 15

Which of the following is the correct product when 1,2-dibromocyclohexane is treated with $$\mathrm{$$NaNH_2$$}$$?

Accepted Answer

Cyclohexyne

Question 16

Which of the following is the correct product when 1-chloro-2-methylpropene is treated with $$\mathrm{NaOH}$$?

Accepted Answer

2-methyl-2-propen-1-ol

Question 17

Which of the following is the correct product when 1,2-dibromopropane is treated with excess $$\mathrm{$$NaNH_2$$}$$?

Accepted Answer

Propyne

Question 18

Which of the following is the correct product when 1,2-epoxypropane is treated with $$\mathrm{NaCN}$$?

Accepted Answer

2-cyano-1-propanol

Stepwise Mechanism for Epoxide Ring Opening with Nucleophile

스터디 가이드 - 연습 문제