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Exam 11: Reactions of Alcohols

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Question 21

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Provide the structure of the major organic product in the reaction below. PhCH₂CH₂OH →

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Question 22

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Provide the major organic product of the following reaction.

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Question 23

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Provide the structure of the major organic product in the reaction below. (CH₃)₂CHCH₂OH

Predict the outcome of the following sequence of reactions.

Provide the structure of the major organic product in the reaction below.

What series of synthetic steps could be used to prepare hexan-3-ol from propan-1-ol?

Why are alcohols unreactive toward nucleophilic substitution reactions?

Which of the following reagents can be used to convert cyclopentanol to cyclopentane?

Provide the name of the major organic product that results when trans-4-methylcyclohexanol is treated with Lucas reagent.

Draw the structure of dimethyl sulfate, and provide a mechanism for the reaction of this compound with sodium benzoate (PhCO₂Na).

Provide the major organic product of the reaction shown.

Chromic acid oxidations are believed to proceed through a chromate ester intermediate. In the oxidation of propran-1-ol, provide the structure of this ester and give the mechanism for its conversion to the intermediate aldehyde.

Provide the name of the major organic product that results when cyclopentanol is subjected to the following sequence of reactions: 1. NaH; 2. CH₃CH₂Br.

What series of synthetic steps could be used to carry out the transformation shown below?

Provide the structure of the major organic product in the reaction below.

What is the expected product of the reaction below?

Provide the major organic product of the reaction shown.

Predict the major product of the following dehydration reaction.

Describe the composition of the Jones reagent.

When an alcohol is heated in concentrated H₂SO₄, dehydration to produce both alkenes and ethers is possible. Which process is more favored by higher reaction temperatures and why?