How can the following compounds be prepared from the given starting materials?
a.

In each part, rank the compounds in order of increasing rate of nucleophilic attack at C=O by a strong nucleophile like methoxide.

(a)

Show how you would convert 2-methylcyclopentanol to the following products. Any of these products may be used as the reactant in any subsequent part of this problem.

(g) 2-methylcyclopentyl acetate

(h) 1-bromo-1-methylcyclopentane

Predict the product of the multistep synthesis reaction shown.

Predict the product of the following reaction sequences.

(a)

Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.

(a) Ph₃C–OH

(b) (PhCH₂)₂CHOH

(c) PhCONHCH₂CH₃

Show how to synthesize the following amines from the indicated starting materials by acylation–reduction.

(a) N-butylpiperidine from piperidine

(b) N-benzylaniline from aniline

Which compound forms an anhydride more rapidly?

b. What is the product of the reaction of acetamide with HO⁻? The pK_a of NH₃ is 36; the pK_a of H₂O is 15.7.