Question 1

Which reagent combination is used to convert an alkyne to a trans-alkene in a selective reduction reaction?

Accepted Answer

$$\mathrm{Na}$$, $$\mathrm{NH}_3$$

Question 2

In the reaction of 1-butyne with $$\mathrm{Na} in $$liquid $$\mathrm{NH}_3$$, what is the major product?

Accepted Answer

trans-2-butene

Question 3

Which of the following best describes the role of benzyltrimethylammonium chloride in the reaction of an alkyl halide with $$\mathrm{NaN}_3$$?

Accepted Answer

It is a phase transfer catalyst.

Question 4

When 2-butyne is treated with Lindlar catalyst and $$\mathrm{H}_2$$, what is the stereochemistry of the product?

Accepted Answer

Cis-alkene

Question 5

Which of the following is the correct product when 1,3-butadiene reacts with $$\mathrm{Cl}_2 in $$water?

Accepted Answer

3-chloro-2-buten-1-ol

Question 6

Which mechanism is responsible for the rapid tautomerization of phenol under acidic conditions?

Accepted Answer

Acid-catalyzed keto-enol tautomerism

Question 7

What is the major product when styrene is treated with $$\mathrm{NaNH}_2$$ followed by $$\mathrm{CH}_3CH_2Br$$ and then $$\mathrm{Cl}_2$$?

Accepted Answer

1-chloro-1-phenylpropane

Question 8

Which of the following is a correct resonance contributor for the benzoate ion?

Accepted Answer

A structure with the negative charge delocalized between both oxygens of the carboxyl group

Question 9

Which reagent would you use to convert a terminal alkyne to a methyl ketone via hydration?

Accepted Answer

$$\mathrm{H}_2\mathrm{O}$$, $$\mathrm{HgSO}_4$$, $$\mathrm{H}_2\mathrm{SO}_4$$

Question 10

What is the expected product when 1,2-dibromopropane is treated with excess $$\mathrm{NaNH}_2$$?

Accepted Answer

Propyne

Question 11

Which of the following best describes the product of hydroboration-oxidation of 2-methyl-2-butene?

Accepted Answer

2-methyl-1-butanol

Question 12

In the multi-step synthesis of 1-butyne from 1-bromobutane, which sequence of reagents is most appropriate?

Accepted Answer

$$\mathrm{NaNH}_2 ($$excess)

Question 13

Which of the following is the correct product when 2-butyne is treated with $$\mathrm{NaNH}_2$$ followed by ethyl bromide?

Accepted Answer

3-ethyl-2-butyne

Question 14

Which of the following is a correct arrow-pushing mechanism for the addition of $$\mathrm{Cl}_2 to an $$alkene in water?

Accepted Answer

Formation of a cyclic chloronium ion followed by nucleophilic attack by water

Question 15

Which of the following reagents would convert a terminal alkyne to an aldehyde?

Accepted Answer

$$\mathrm{BH}_3$$, $$\mathrm{NaOH}$$

Question 16

Which of the following is the correct product when 1,3-butadiene is treated with $$\mathrm{Cl}_2 (1 $$equiv) in water?

Accepted Answer

3-chloro-2-buten-1-ol

Question 17

Which of the following is a correct resonance contributor for the nitro group ($$\mathrm{NO}_2) $$attached to benzene?

Accepted Answer

A structure with a positive charge on the nitrogen and negative charges on both oxygens

Question 18

Which of the following is the correct product when 2-butyne is treated with $$\mathrm{NaNH}_2$$ and then $$\mathrm{CH}_3CH_2Br$$?

Accepted Answer

3-ethyl-2-butyne

Question 19

Which of the following is the correct sequence of reagents to convert an alkene to a vicinal diol?

Accepted Answer

$$\mathrm{OsO}_4$$, $$\mathrm{NaHSO}_3$$

Organic Chemistry: Mechanisms, Reactions, and Synthesis Study Guide

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