Question 1

In the first image, the compound X is treated with reagent Y to give two carbonyl compounds: butanal and acetone. What is the identity of reagent Y?

Accepted Answer

Ozone, followed by dimethyl sulfide ($$O_3$$, then $$(CH_3$)_2S)$$

Question 2

In the first image, the bottom reaction uses $$(COCl)_2/$$DMSO and $$Et_3N to $$convert compound X into a product. What is the name of this reaction?

Accepted Answer

Swern oxidation

Question 3

In the first image, what is the functional group transformation that occurs when X is treated with $$(COCl)_2/$$DMSO and $$Et_3N$$?

Accepted Answer

Secondary alcohol to ketone

Question 4

In the second image, what is the major product when 2-methylpropene reacts with $$Br_2$$ and $$H_2O$$?

Accepted Answer

2-bromo-2-methylpropan-1-ol (structure 1)

Question 5

In the reaction shown in the second image, what is the mechanism for the addition of $$Br_2$$ and $$H_2O to 2-$$methylpropene?

Accepted Answer

Anti addition via a bromonium ion intermediate

Question 6

In the third image, what is the major product when 1-methyl-4-methylcyclohexene is hydrogenated over Pt?

Accepted Answer

Cis-1,4-dimethylcyclohexane (structure 1)

Question 7

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

Accepted Answer

Both methyl groups are on the same side of the ring (cis)

Question 8

In the first image, what is the role of $$(COCl)_2 in $$the Swern oxidation?

Accepted Answer

Activates DMSO to form an electrophilic sulfonium species

Question 9

In the second image, which product would result from Markovnikov addition of $$Br_2$$ and $$H_2O to 2-$$methylpropene?

Accepted Answer

2-bromo-2-methylpropan-1-ol (structure 1)

Question 10

In the third image, what is the effect of using a platinum catalyst in the hydrogenation of the cyclohexene derivative?

Accepted Answer

It results in syn addition of hydrogen to the double bond

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