Question 1

Which of the following statements best describes the difference between Markovnikov and anti-Markovnikov addition in hydrohalogenation of alkenes?

Accepted Answer

Markovnikov addition places the halogen on the more substituted carbon, while anti-Markovnikov addition places it on the less substituted carbon.

Question 2

Which reagent(s) would you use to convert an alkyne to a cis-alkene selectively?

Accepted Answer

$$\mathrm{H_2$}$$, Lindlar's catalyst

Question 3

Which of the following best explains why catalytic hydrogenation of alkenes requires a metal catalyst?

Accepted Answer

The catalyst lowers the activation energy ($$E_a) by $$providing a surface for the reaction.

Question 4

What is the major organic product when 1-butene reacts with $$\mathrm{HBr} in $$the presence of peroxides?

Accepted Answer

1-bromobutane

Question 5

Which of the following reactions will result in the formation of a vicinal diol (syn addition of two OH groups)?

Accepted Answer

Osmium tetroxide ($$\mathrm{$$OsO_4$$}) $$followed by $$\mathrm{$$NaHSO_3$$}$$

Question 6

A terminal alkyne is treated with sodium amide ($$\mathrm{$$NaNH_2$$}) $$followed by ethyl bromide ($$\mathrm{C_2H_5Br}). $$What is the major product?

Accepted Answer

An internal alkyne with an ethyl group added to the terminal carbon

Question 7

Which of the following best describes the product(s) of ozonolysis of 2-butene?

Accepted Answer

Two molecules of acetaldehyde ($$\mathrm{CH_3CHO})$$

Question 8

Which of the following statements about the hydration of alkynes is correct?

Accepted Answer

Acid-catalyzed hydration of a terminal alkyne gives a ketone as the final product.

Question 9

Which of the following is true regarding the stereochemistry of halogenation of alkenes?

Accepted Answer

The addition of halogens is always anti.

Question 10

Which of the following reagents would you use to convert 1-hexyne to hexanal?

Accepted Answer

$$\mathrm{R_2BH}$$, $$\mathrm{H_2O_2}$$, $$\mathrm{NaOH}$$

Question 11

Which of the following best describes the mechanism of acid-catalyzed hydration of alkenes?

Accepted Answer

The reaction proceeds via a carbocation intermediate and follows Markovnikov's rule.

Question 12

Which of the following is a key difference between oxymercuration-demercuration and acid-catalyzed hydration of alkenes?

Accepted Answer

Oxymercuration-demercuration avoids carbocation rearrangement and does not involve equilibrium issues.

Question 13

Which of the following best describes the product of the reaction of 2-methyl-2-butene with $$\mathrm{BH_3$} in $$THF followed by $$\mathrm{H_2O_2}$$ and $$\mathrm{NaOH}$$?

Accepted Answer

3-methyl-2-butanol (anti-Markovnikov alcohol)

Question 14

Which of the following statements about the halohydrin formation reaction is correct?

Accepted Answer

The halogen adds to the less substituted carbon and the OH adds to the more substituted carbon.

Question 15

Which of the following is the correct product of ozonolysis of 1-hexyne?

Accepted Answer

One molecule of hexanoic acid and one molecule of carbon dioxide

Addition and Related Reactions of Alkenes and Alkynes

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