Question 1

Which of the following reagents will convert a terminal alkyne to a cis-alkene?

Accepted Answer

$$\mathrm{Lindlar's\ catalyst}, \mathrm{H}_2$$

Question 2

What is the major product when cyclohexene is treated with $$\mathrm{Br}_2 in$$ $$\mathrm{CCl}_4$$?

Accepted Answer

trans-1,2-dibromocyclohexane

Question 3

Which sequence of reagents will convert 1-bromocyclohexane to cyclohexanecarboxylic acid?

Accepted Answer

$$1. \mathrm{Mg}, \mathrm{THF};\ 2. \mathrm{CO}_2;\ 3. \mathrm{H}_3\mathrm{O}^+$$

Question 4

A terminal alkyne undergoes hydroboration-oxidation. What is the major product?

Accepted Answer

An aldehyde

Question 5

Which of the following best describes the stereochemistry of the product formed when cyclohexene reacts with $$\mathrm{Br}_2 in$$ $$\mathrm{CCl}_4$$?

Accepted Answer

Racemic mixture of trans-1,2-dibromocyclohexane

Question 6

What is the product of the following reaction sequence: $$1. \mathrm{NaNH}_2 ($$excess), $$2. \mathrm{EtBr}$$, $$3. \mathrm{H}_2, \mathrm{Lindlar's\ catalyst}$$ starting from 1-butyne?

Accepted Answer

cis-2-hexene

Question 7

Which reagent is required to convert a cyclohexanol to cyclohexanone?

Accepted Answer

$$\mathrm{Na}_2\mathrm{Cr}_2\mathrm{O}_7, \mathrm{H}_2SO_4$$

Question 8

Which of the following is the correct mechanism for the acid-catalyzed hydration of an alkene?

Accepted Answer

Carbocation intermediate followed by nucleophilic attack by water

Question 9

What is the major product when 1-methylcyclohexene is treated with $$\mathrm{Hg(OAc)_2}$$, $$\mathrm{H_2O}$$ followed by $$\mathrm{$$NaBH_4$$}$$?

Accepted Answer

1-methylcyclohexanol (Markovnikov addition)

Question 10

Which of the following transformations is an example of anti-Markovnikov addition?

Accepted Answer

Hydroboration-oxidation of alkenes

Question 11

A student attempts to synthesize 1-bromocyclohexane from cyclohexene. Which reagent should they use?

Accepted Answer

$$\mathrm{HBr}$$

Question 12

Which of the following is the correct product when 1-butyne is treated with $$\mathrm{HgSO}_4$$ and $$\mathrm{H_2SO_4}$$?

Accepted Answer

2-butanone

Question 13

What is the major product when cyclohexene is treated with $$\mathrm{mCPBA}$$?

Accepted Answer

Cyclohexene oxide (epoxide)

Question 14

Which of the following best describes the product of the reaction: $$\mathrm{CH}_3CH_2CH_2CH_2Br + \mathrm{NaCN}$$?

Accepted Answer

Butanenitrile ($$\mathrm{CH}_3CH_2CH_2CH_2CN)$$

Question 15

Which of the following reagents will convert a primary alcohol to a carboxylic acid?

Accepted Answer

$$\mathrm{Na}_2\mathrm{Cr}_2\mathrm{O}_7, \mathrm{H}_2SO_4$$

Question 16

Which of the following is the correct product when 1-hexene is treated with $$\mathrm{Br}_2 in$$ $$\mathrm{CCl}_4$$?

Accepted Answer

trans-1,2-dibromohexane

Question 17

Which of the following reagents will convert cyclohexanone to cyclohexanol?

Accepted Answer

$$\mathrm{NaBH}_4$$

Question 18

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

Accepted Answer

Cyclohexanecarbonitrile

Question 19

Which of the following best describes the product of the reaction: $$\mathrm{CH}_3CH_2CH_2CH_2Br + \mathrm{NaOH}$$?

Accepted Answer

1-butanol ($$\mathrm{CH}_3CH_2CH_2CH_2OH)$$

Advanced Organic Chemistry Reaction Mechanisms and Synthesis Study Guide

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