Question 1

Which reagent is commonly used for the hydroboration-oxidation of alkenes, resulting in anti-Markovnikov addition of water across the double bond?

Accepted Answer

1. BH$$_3/$$THF, 2. H$$_2O$_2/H$_2O/$$NaOH

Question 2

In the reaction of 3-methyl-2-pentene with Br$$_2$$ and H$$_2O$$, what is the major product formed?

Accepted Answer

2-bromo-3-methylpentan-2-ol

Question 3

Which of the following best describes the mechanism for the addition of Br$$_2$$ and H$$_2O to an $$alkene?

Accepted Answer

Electrophilic addition followed by nucleophilic attack by water

Question 4

When butyne reacts with 1 equivalent of Cl$$_2$$ followed by 1 equivalent of HBr, what is the expected major product?

Accepted Answer

2-bromo-1-chlorobutene

Question 5

Which of the following reagents is used for the catalytic hydrogenation of alkenes to alkanes?

Accepted Answer

H$$_2/Pd$$

Question 6

What is the product when an alkene reacts with 2 equivalents of Cl$$_2$$?

Accepted Answer

A tetra-chloroalkane

Question 7

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

Accepted Answer

Hydroboration-oxidation gives anti-Markovnikov alcohols, while acid-catalyzed hydration gives Markovnikov alcohols.

Question 8

Which of the following alkenes or alkynes would produce two carboxylic acids upon oxidative cleavage?

Accepted Answer

An internal alkyne such as 2-butyne

Question 9

In the addition of HBr to an alkene, which rule determines the regioselectivity of the product?

Accepted Answer

Markovnikov's rule

Question 10

A student wants to convert an alkene to a vicinal diol. Which reagent should they use?

Accepted Answer

OsO$$_4$$ followed by H$$_2O$_2$$

Question 11

Which product is formed when an alkyne undergoes hydration with H$$_2O$$, H$$_2SO$_4$$, and HgSO$$_4$$?

Accepted Answer

A ketone via Markovnikov addition

Question 12

Which of the following best explains why hydroboration-oxidation of an alkene leads to anti-Markovnikov alcohols?

Accepted Answer

Boron adds to the less substituted carbon due to steric and electronic factors

Question 13

A patient is exposed to a compound containing a terminal alkyne. Which product would result from oxidative cleavage of this alkyne?

Accepted Answer

A carboxylic acid and carbon dioxide

Question 14

Which step occurs first in the mechanism of bromohydrin formation from an alkene and Br$$_2 in $$water?

Accepted Answer

Formation of a bromonium ion

Question 15

Which of the following is the correct sequence of reagents for converting an alkyne to a cis-alkene?

Accepted Answer

H$$_2$$ and Lindlar's catalyst

Question 16

A chemist wants to synthesize a Markovnikov alcohol from an alkene. Which reagent should they use?

Accepted Answer

H$$_2O/H$_2SO$_4$$

Question 17

Which product is formed when 1 eq. HBr is added to an alkene?

Accepted Answer

A bromoalkane with the Br on the more substituted carbon

Question 18

Which of the following best describes the product of catalytic hydrogenation of an alkyne?

Accepted Answer

An alkane

Question 19

Which of the following is a plausible intermediate in the mechanism for the addition of Br$$_2 to an $$alkene?

Accepted Answer

Bromonium ion

Organic Chemistry Problem Set Guidance: Reagents, Mechanisms, and Oxidation Products

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