Rank the following anions based on their stability as potential leaving groups. Explain your reasoning (1 = most stable ; 5 = least stable).

Would you expect a ketone or an ester to be more reactive with a strong nucleophile? Justify your answer.

Which of the following are considered carboxylic acid derivatives?

(a)

Provide the IUPAC name for the following molecules.

(d)

Provide the IUPAC name for the following molecules.

(e)

Provide a molecular structure that corresponds to the given name.

(a) benzoic propanoic anhydride

Provide a molecular structure that corresponds to the given name.

(e) (R)-N,N-diethyl 5-cyclohexyl-3-methoxypentanamide

Predict the hybridization of the indicated atoms.

(b)

How would you expect the IR and ¹H NMR spectra for propanamide and N,N-diethylpropanamide to differ?

You might expect that aldehydes and ketones could undergo the addition/elimination mechanism. With strong nucleophiles, however, nucleophilic addition is the only outcome. Why?

A chemist unsuccessfully attempted to produce the 1,4-cyclohexanediol by hydration of the cyclohexene shown.

(a) Provide a mechanism for the formation of the actual product.

(b) Suggest a pathway using acetyl chloride as a protecting group that will allow for the formation of the desired product.

Predict the product of the following reductions.

(a)

Predict the product of the following reductions.

(b)

Predict the product of the following reductions.

(c)

Predict the product of the following reductions.

(d)

Show a mechanism for the lithium aluminum hydride reduction of benzoic anhydride.

Predict the product of the multistep synthesis reaction shown.

Predict the product of the following reaction sequences.

(a)

Predict the product of the following reaction sequences.

(b)

Predict the product of the following reaction sequences.

(c)

The esters shown differ only by the alkoxy group.

(i) Predict the product(s) obtained when these react with DIBAl-H.

(ii) Based on your answer, in a sequence like this, would there ever be a need to convert from one ester to another?

(a)

The esters shown differ only by the alkoxy group.

(i) Predict the product(s) obtained when these react with DIBAl-H.

(ii) Based on your answer, in a sequence like this, would there ever be a need to convert from one ester to another?

(b)

When the ester attacked the aluminum of DIBAl-H, why did the carbonyl oxygen attack preferentially over the alkoxy oxygen?

Why is a ketone more reactive/electrophilic than an ester?

Predict the product of the following reactions.

(a)

Predict the product of the following reactions.

(b)

Predict the product of the following reactions.

(c)

Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.

(a)

Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.

(b)

Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.

(c)