Question 1

Which reagent is most suitable for converting a primary alcohol to an aldehyde without over-oxidation to a carboxylic acid?

Accepted Answer

Swern oxidation (DMSO, oxalyl chloride, Et$$_3N)$$

Question 2

In the reaction where cyclohexanone is heated, which type of reaction mechanism is most likely to occur?

Accepted Answer

Dehydration to form an enone

Question 3

A compound with the structure PhCO$$_2H ($$benzoic acid) can be synthesized from which of the following starting materials using oxidation?

Accepted Answer

Toluene

Question 4

Which of the following best describes the role of Et$$_3N ($$triethylamine) in the Swern oxidation?

Accepted Answer

It neutralizes the acidic byproducts formed during the reaction.

Question 5

When a compound containing a diazonium group is exposed to light, what is the most likely outcome?

Accepted Answer

Loss of N$$_2$$ and formation of a carbocation

Question 6

Which of the following reactions is used to convert a cyclohexyl methyl group to a benzene ring?

Accepted Answer

Aromatization using heat and a catalyst

Question 7

A student attempts to convert cyclohexene to benzene. Which sequence of reactions would be most effective?

Accepted Answer

Dehydrogenation using Pd/C and heat

Question 8

Which of the following is a key intermediate in the Swern oxidation mechanism?

Accepted Answer

Alkoxysulfonium ion

Question 9

In the conversion of a cyclohexanone to phenol, which step is essential?

Accepted Answer

Oxidative aromatization

Question 10

A student uses light to initiate a reaction with a compound containing a diazonium group. What is the major product?

Accepted Answer

An aryl radical

Question 11

Which of the following best explains why Swern oxidation is preferred over Jones oxidation for sensitive substrates?

Accepted Answer

Swern oxidation uses milder conditions and avoids water, preventing over-oxidation.

Question 12

What is the product when cyclohexanone is heated in the presence of a strong base?

Accepted Answer

Phenol

Question 13

Which of the following is NOT a plausible product of the Swern oxidation of a secondary alcohol?

Accepted Answer

Carboxylic acid

Question 14

A student wants to convert a cyclohexyl chloride to benzene. Which reaction sequence is most appropriate?

Accepted Answer

Elimination to cyclohexene, followed by dehydrogenation

Question 15

Which of the following is a common misconception about the Swern oxidation?

Accepted Answer

It can oxidize primary alcohols to carboxylic acids.

Question 16

In the conversion of a cyclohexanone to benzene, which intermediate is most likely formed?

Accepted Answer

Phenol

Question 17

Which of the following best describes the mechanism of the Swern oxidation?

Accepted Answer

Formation of an alkoxysulfonium ion followed by base-induced elimination

Question 18

A student exposes a diazonium salt to light. What is the most likely fate of the diazonium group?

Accepted Answer

It is lost as N$$_2$$, forming an aryl radical.

Question 19

Which of the following is a necessary condition for the Swern oxidation to proceed efficiently?

Accepted Answer

Low temperature (below 0$$^	ext{o}C)$$

Question 20

Which of the following is the correct order of steps in the Swern oxidation mechanism?

Accepted Answer

Activation of DMSO, formation of alkoxysulfonium ion, base-induced elimination

Organic Reaction Mechanisms and Aromatic Compound Synthesis – CHEM7121 Homework Study Notes

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