Question 1

Which mechanism is responsible for the formation of the alcohol in the reaction shown in $$image_1 ($$cyclohexene + H2O/H2SO4)?

Accepted Answer

Acid-catalyzed hydration (Markovnikov addition)

Question 2

In $$image_2$$, why does oxymercuration-demercuration avoid carbocation rearrangements compared to acid-catalyzed hydration?

Accepted Answer

Because the reaction proceeds via a mercurinium ion intermediate

Question 3

In the hydroboration-oxidation reaction shown in $$image_3$$, what is the regiochemistry of the alcohol product?

Accepted Answer

Anti-Markovnikov addition

Question 4

What is the major product of the reaction shown in $$image_4 ($$ethyl iodide + NaOCH2CH3 in ethanol)?

Accepted Answer

Ethyl ether ($$CH_3CH_2OCH_2CH_3)$$

Question 5

What is the product of the reaction shown in $$image_5 ($$cyclohexene + mCPBA)?

Accepted Answer

Cyclohexene oxide (epoxide)

Question 6

What is the result of treating benzyl methyl ether ($$C_6H_5CH_2OCH_3) $$with excess concentrated HBr and heat as shown in $$image_6$$?

Accepted Answer

Benzyl bromide and methyl bromide

Question 7

In $$image_7$$, what is the product of the reaction between the epoxide and HCl?

Accepted Answer

A chlorohydrin

Question 8

What is the major product when the ether in $$image_8 is $$treated with 1 equivalent of HBr and heat?

Accepted Answer

A single alkyl bromide and an alcohol

Question 9

According to $$image_9$$, which functional group has the highest oxidation state?

Accepted Answer

Carboxylic acid

Question 10

Based on $$image_10$$, what is the product of reducing a ketone with NaBH4?

Accepted Answer

Secondary alcohol

Question 11

In $$image_11$$, what is the major product of the reaction sequence: NaBH4 reduction followed by ethylene oxide addition and acid workup?

Accepted Answer

A primary alcohol with two additional carbons

Question 12

What is the purpose of using ether as a solvent in the formation of Grignard reagents as shown in $$image_12$$?

Accepted Answer

To stabilize the Grignard reagent via coordination

Question 13

In the multi-step sequence shown in $$image_13$$, what is the role of Mg in the second step?

Accepted Answer

It converts the alkyl bromide to a Grignard reagent

Question 14

In $$image_14$$, what is the expected product when CH3MgI reacts with the compound containing both a carboxylic acid and a ketone group?

Accepted Answer

Addition to both the ketone and carboxylic acid, followed by reduction to a tertiary alcohol

Question 15

In $$image_15$$, why is the alcohol group protected before the Grignard reaction?

Accepted Answer

To prevent the alcohol from reacting with the Grignard reagent

Question 16

What is the product of the Diels-Alder reaction shown in $$image_16$$?

Accepted Answer

A bicyclic compound with one double bond and two carbonyl groups

Question 17

Which of the following statements about resonance in conjugated systems is correct?

Accepted Answer

Electrons move during resonance, increasing stability

Question 18

Why is chromic acid (Jones reagent) preferred for oxidizing alcohols in laboratory settings?

Accepted Answer

It provides a visible color change from orange to green

Question 19

Which reagent would you use to selectively oxidize a primary alcohol to an aldehyde without further oxidation to a carboxylic acid?

Accepted Answer

PCC

Alcohols, Ethers, Redox, Grignard, and Conjugated Systems: Orgo II Exam 1 Study Guide

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