Q: Which reagent is used for oxymercuration-demercuration of alkenes, resulting in Markovnikov addition of water across the double bond without carbocation rearrangement?

1) $$\text{Hg(OAc)}_2$$, $$\text{H}_2\text{O}$$; 2) $$\text{NaBH}_4$$

Q: Which of the following reagents will convert an alkyne to a cis-alkene?

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

Q: Which reaction sequence would you use to convert an alkene to an anti-Markovnikov alcohol?

1) $$\text{BH}_3$$, $$\text{THF}$$; 2) $$\text{H}_2\text{O}_2$$, $$\text{NaOH}$$

Q: Which reagent is used to reduce an alkyne to a trans-alkene?

$$\text{Na}$$, $$\text{NH}_3 ($$liq)

Q: Which reaction would you use to convert an alkene to a vicinal dihalide?

$$\text{Br}_2$$, $$\text{CCl}_4$$

Q: Which sequence is used to alkylate a terminal alkyne?

1) $$\text{NaNH}_2$$; 2) $$\text{RBr}$$

Q: Which of the following reactions is used to synthesize an alkane from an alkene?

$$\text{H}_2$$, $$\text{Pd/C}$$

Q: Which reagent is used for syn addition of hydrogen to an alkyne?

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

Question 1

Which reagent is used for oxymercuration-demercuration of alkenes, resulting in Markovnikov addition of water across the double bond without carbocation rearrangement?

Accepted Answer

1) $$	ext{Hg(OAc)}_2$$, $$	ext{H}_2	ext{O}$$; 2) $$	ext{NaBH}_4$$

Question 2

What is the product of the reaction of an alkene with $$	ext{Br}_2 in$$ $$	ext{CCl}_4$$?

Accepted Answer

A vicinal dibromide

Question 3

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

Accepted Answer

$$	ext{H}_2$$, $$	ext{Lindlar's catalyst}$$

Question 4

A terminal alkyne reacts with $$	ext{NaNH}_2$$ followed by $$	ext{CH}_3	ext{Br}. $$What is the major product?

Accepted Answer

An internal alkyne with a methyl group added

Question 5

Which reaction sequence would you use to convert an alkene to an anti-Markovnikov alcohol?

Accepted Answer

1) $$	ext{BH}_3$$, $$	ext{THF}$$; 2) $$	ext{H}_2	ext{O}_2$$, $$	ext{NaOH}$$

Question 6

What is the stereochemistry of the product when an alkene reacts with $$	ext{Br}_2 in$$ $$	ext{CCl}_4$$?

Accepted Answer

Anti addition

Question 7

Which reagent is used to reduce an alkyne to a trans-alkene?

Accepted Answer

$$	ext{Na}$$, $$	ext{NH}_3 ($$liq)

Question 8

Which of the following is a good nucleophile for alkylation of terminal alkynes?

Accepted Answer

$$	ext{NaNH}_2$$

Question 9

What is the outcome when an alkene is treated with $$	ext{H}_2$$ and $$	ext{Pd/C}$$?

Accepted Answer

The alkene is reduced to an alkane

Question 10

Which of the following best describes the regioselectivity of oxymercuration-demercuration of alkenes?

Accepted Answer

Markovnikov addition

Question 11

A student wants to synthesize a cis-alkene from an alkyne. Which catalyst should they use?

Accepted Answer

Lindlar's catalyst

Question 12

Which reaction would you use to convert an alkene to a vicinal dihalide?

Accepted Answer

$$	ext{Br}_2$$, $$	ext{CCl}_4$$

Question 13

Which of the following is NOT a product of the reaction of an alkene with $$	ext{BH}_3$$, $$	ext{THF}$$ followed by $$	ext{H}_2	ext{O}_2$$, $$	ext{NaOH}$$?

Accepted Answer

Markovnikov alcohol

Question 14

Which sequence is used to alkylate a terminal alkyne?

Accepted Answer

1) $$	ext{NaNH}_2$$; 2) $$	ext{RBr}$$

Question 15

What is the major product when an alkyne is treated with excess $$	ext{Br}_2$$?

Accepted Answer

A tetrahalide

Question 16

Which of the following reactions is used to synthesize an alkane from an alkene?

Accepted Answer

$$	ext{H}_2$$, $$	ext{Pd/C}$$

Question 17

Which reagent is used for syn addition of hydrogen to an alkyne?

Accepted Answer

$$	ext{H}_2$$, 	ext{Lindlar's catalyst}$

Question 18

Which of the following is a common misconception about the reaction of alkenes with $$	ext{Hg(OAc)}_2$$, $$	ext{H}_2	ext{O}$$ followed by $$	ext{NaBH}_4$$?

Accepted Answer

That carbocation rearrangement occurs

Summary of Alkene and Alkyne Reactions: Addition and Synthesis Pathways

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