Question 1

In the first image, the compound X undergoes two different reactions. The first reaction (Y) produces acetone and propanal, while the second reaction uses $$(	ext{COCl}_2)/	ext{DMSO}$$ and $$	ext{Et}_3	ext{N} to $$produce a β-hydroxy ketone. What are the identities of X and Y, and what is the name of the reaction Y?

Accepted Answer

X is 2-methylpentane-2,3-diol, Y is HIO4, and Y is a periodate cleavage (oxidative cleavage of vicinal diols)

Question 2

In the second image, isopropene reacts with $$	ext{Br}_2$$ and $$	ext{H}_2	ext{O}. $$Which product is the major organic product?

Accepted Answer

2

Question 3

In the third image, methylcyclohexene is hydrogenated with $$	ext{H}_2$$ and platinum. Which product is the major organic product?

Accepted Answer

1

Question 4

Which of the following best describes the mechanism for the addition of $$	ext{Br}_2$$ and $$	ext{H}_2	ext{O} to an $$alkene, as shown in the second image?

Accepted Answer

Electrophilic addition via a cyclic bromonium ion intermediate, followed by nucleophilic attack by water

Question 5

In the first image, the reaction with $$(	ext{COCl}_2)/	ext{DMSO}$$ and $$	ext{Et}_3	ext{N} is an $$example of which named reaction?

Accepted Answer

Swern oxidation

Question 6

Which product is formed when methylcyclohexene is hydrogenated with $$	ext{H}_2$$ and platinum, as shown in the third image?

Accepted Answer

Cis-1,2-dimethylcyclohexane

Question 7

Which of the following statements about the periodate cleavage reaction (Y in the first image) is correct?

Accepted Answer

It cleaves vicinal diols to give two carbonyl compounds

Question 8

In the second image, what is the regiochemistry of the addition of $$	ext{Br}_2$$ and $$	ext{H}_2	ext{O} to $$the alkene?

Accepted Answer

Br adds to the less substituted carbon, OH adds to the more substituted carbon

Question 9

Which of the following best describes the stereochemistry of the hydrogenation reaction in the third image?

Accepted Answer

Syn addition of hydrogen atoms to the double bond

Question 10

Which of the following is a plausible reason why the product in the second image is 2 and not 1, 3, or 4?

Accepted Answer

The reaction proceeds via a cyclic bromonium ion, and water attacks the more substituted carbon, leading to Markovnikov addition

Organic Chemistry Exam Review: Alkenes, Alkynes, Alcohols, and Phenols

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