When HCl was used for the attempted dehydration reaction shown, a reaction occurred, but none of the desired product was formed. Suggest the identity of the actual product obtained.

Predict which side of the equilibrium is favored by ∆H, ∆G, and ∆S.

Predict the major product of the following elimination reactions.

(a)

Predict the major product of the following elimination reactions.

(b)

Predict the major product of the following elimination reactions.

(c)

Identify the alcohol(s) that would produce the following alkenes under the given conditions.

(a)

Identify the alcohol(s) that would produce the following alkenes under the given conditions.

(b)

Identify the alcohol(s) that would produce the following alkenes under the given conditions.

(c)

Treatment of the following alcohol was expected to give alkene A. Instead, B was produced as the major product. Suggest a mechanism by which B formed.

Predict the product(s) of the reactions shown.

(a)

Predict the product(s) of the reactions shown.

(b)

Identify two different alcohols that can be dehydrated (one with rearrangement) to form the alkene shown.

Identify two different alcohols that can be dehydrated (one without rearrangement) to form the alkene shown.

Show a reaction coordinate diagram for the two processes in Figure 13.41 that rationalizes pathway B as the one that gives the major product.

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Predict the product of the following pinacol rearrangements.

(b)

Predict the product of the following pinacol rearrangements.

(c)

Suggest an alkene that, in two steps, could be converted into each of the following ketones. Each sequence should involve a pinacol rearrangement.

(c)

The intermediates for the Swern oxidation, a reaction introduced in Section 13.9.4, are shown. Provide the arrow-pushing mechanism that rationalizes the formation of each intermediate and the final product(s).

In Assessment 13.48, identify the individual step that represents the general mechanism for all alcohol oxidation reactions.

Every oxidation is accompanied by a reduction. Identify the species that is reduced in the Swern oxidation in Assessment 13.48.

Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.

(a)

Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.

(b)

Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.

(c)

Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.

(d)

Predict the product of the oxidation reactions shown.

(a)

Predict the product of the oxidation reactions shown.

(b)

The intermediates for the oxidation of isopropanol to acetone are shown. Calculate oxidation numbers for the indicated atoms, then use them to determine in which step oxidation occurs.

(e)

Tertiary (3°)alcohols are not oxidized by chromic acid. Why?

Though ketones, like aldehydes, are in equilibrium with a hydrated form, they cannot be further oxidized. Why?

If there is no water present, the hydrate of an aldehyde cannot form. Could an aldehyde itself (not the hydrate) be oxidized to a carboxylic acid? Why?