Rank the ability of the following compounds to undergo an S_N1 reaction ( 1 = fastest, 5 = slowest ).

Provide a mechanism for the following S_N1 reaction. What roles (acid/base/nucleophile/electrophile) does ethanol play in the reaction? What functional group is made in this reaction?

Use oxidation numbers to determine whether the following are redox reactions.

(a)

Use oxidation numbers to determine whether the following are redox reactions.

(b)

The mechanism of the acid-catalyzed hydration of an alkene to make an alcohol is shown. If this reaction is reversible, draw a mechanism that justifies formation of the alkene from the alcohol under similar conditions. How do you know this mechanism is correct?

Provide the IUPAC name for the following molecules.

(a)

Provide the IUPAC name for the following molecules.

(b)

Provide the IUPAC name for the following molecules.

(f)

Draw the structure that corresponds to the name provided.

(a) (1R,5S)-5-methylcyclohex-3-enol

Draw the structure that corresponds to the name provided.

(b) (2R,3R,4S)-heptane-2,3,4-triol

Draw the structure that corresponds to the name provided.

(c) (2E,4S,6Z)-octa-2,6-dien-4-ol

Draw the structure that corresponds to the name provided.

(d) (2R,4Z)-5-bromopent-4-ene-1,2-diol

Draw the structure that corresponds to the name provided.

(e) (1S,4S)-4-isopropylcyclopent-2-enethiol

Label each hydroxyl group in Assessment 13.6 as primary (1°) secondary (2°) , or tertiary (3°) 

Label each sulfhydryl group as primary (1°) secondary (2°) , or tertiary (3°)

Identify the substitution of carbons (a)–(d) comprising the ether functional group in the following molecules.

Show a mechanism for each of the alcohol synthesis reactions in Table 13.8.

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Predict the product of each of the following alcohol synthesis reactions.

(a)

Predict the product of each of the following alcohol synthesis reactions.

(b)

Predict the product of each of the following alcohol synthesis reactions.

(c)

Predict the product of each of the following alcohol synthesis reactions.

(d)

Suggest a reagent to carry out each of the following conversions to an alcohol.

(a)

Suggest a reagent to carry out each of the following conversions to an alcohol.

(b)

Suggest a reagent to carry out each of the following conversions to an alcohol.

(c)

Suggest a reagent to carry out each of the following conversions to an alcohol.

(d)

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.

(a)

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.

(b)

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.

(c)

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.

(d)

Suggest an arrow-pushing mechanism for the following reaction. Is the hydroxyl group acting as a base, acid, Lewis base, or Lewis acid?