Question 1

Which product is formed when cyclohexanone is treated with $$\mathrm{H_2O}$$, $$\mathrm{H_2SO_4} ($$cat.) in an acid-catalyzed hydration reaction?

Accepted Answer

Cyclohexanol ($$\mathrm{C_6H_{11}OH})$$

Question 2

What is the major product when diphenylacetylene ($$\mathrm{C_6H_5C \equiv CC_6H_5}) is $$reduced with lithium in liquid ammonia?

Accepted Answer

Trans-stilbene ($$\mathrm{trans-C_6H_5CH=CHC_6H_5})$$

Question 3

A terminal alkyne is treated first with $$\mathrm{1.\ $$LiNH_2$$}$$ and then with benzyl bromide. What is the major product?

Accepted Answer

An internal alkyne with a benzyl group attached ($$\mathrm{PhCH_2C \equiv CH})$$

Question 4

What is the major product when diphenylacetylene is hydrogenated using Lindlar's catalyst?

Accepted Answer

Cis-stilbene ($$\mathrm{cis-C_6H_5CH=CHC_6H_5})$$

Question 5

When 2-hexyne is treated with excess $$\mathrm{H_2$}$$ and Pd/C, what is the major product?

Accepted Answer

Hexane ($$\mathrm{C_6H_{14}})$$

Question 6

Which reagent would selectively reduce an alkyne to a cis-alkene?

Accepted Answer

Lindlar's catalyst

Question 7

A student wants to convert phenylacetylene ($$\mathrm{C_6H_5C \equiv CH}) to $$ethylbenzene ($$\mathrm{C_6H_5CH_2CH_3}). $$Which sequence of reagents would accomplish this?

Accepted Answer

Excess $$\mathrm{H_2$}$$, Pd/C

Question 8

Which of the following best describes the mechanism of the reduction of alkynes with sodium in liquid ammonia?

Accepted Answer

Anti addition of hydrogen atoms

Question 9

What is the expected product when 1-hexyne is treated with $$\mathrm{$$NaNH_2$$}$$ followed by methyl iodide?

Accepted Answer

2-methyl-1-hexyne

Question 10

Which of the following statements about Lindlar's catalyst is correct?

Accepted Answer

It selectively hydrogenates alkynes to cis-alkenes

Question 11

A chemist wants to synthesize trans-2-butene from 2-butyne. Which reagent should be used?

Accepted Answer

Na/NH$$_3$$

Question 12

Which of the following is a common side product when terminal alkynes are treated with strong base followed by alkyl halide?

Accepted Answer

Double alkylation at the terminal carbon

Question 13

What is the stereochemistry of the alkene formed when diphenylacetylene is reduced with Na/NH$$_3$$?

Accepted Answer

Trans

Question 14

Which of the following reactions is an example of syn addition?

Accepted Answer

Hydrogenation of alkynes with Lindlar's catalyst

Question 15

A patient is exposed to acetylene gas. Which reaction could convert acetylene to ethane in an industrial setting?

Accepted Answer

Hydrogenation with Pd/C

Question 16

Which of the following best explains why Lindlar's catalyst produces cis-alkenes?

Accepted Answer

Hydrogen atoms are added to the same side of the alkyne (syn addition)

Question 17

Which product is formed when 2-butyne is treated with excess $$\mathrm{H_2$}$$ and Pd/C?

Accepted Answer

Butane ($$\mathrm{C_4H_{10}})$$

Question 18

Which reagent would you use to convert a terminal alkyne to a methyl-substituted internal alkyne?

Accepted Answer

$$\mathrm{$$NaNH_2$$}$$, then methyl iodide

Question 19

What is the major product when phenylacetylene is treated with Lindlar's catalyst and $$\mathrm{H_2$}$$?

Accepted Answer

cis-styrene ($$\mathrm{C_6H_5CH=CH_2$})$$

Question 20

Which of the following is NOT a possible product when an alkyne is partially reduced?

Accepted Answer

Alkyl halide

Organic Chemistry: Aromatic and Alkyne Reaction Mechanisms – Self-Quiz Study Notes

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