91Ó°ÊÓ

How would you carry out the following reactions? More than one step may be

required.

(a) 3-Hexyne3-Hexanone

(b) Benzenem-Bromoacetophenone

(c) BromobenzeneAcetophenone

(d) 1-Methylcyclohexene2-Methylcyclohexanone

Primary amines react with esters to yield amides: RCO₂R^' + R^"NH₂ $→$RCONHR^" + R^'OH . Propose a mechanism for the following reaction of an a b-unsaturated ester.

When crystals of pure $\mathrm{Î\pm }$-glucose are dissolved in water, isomerization occurs slowly to produce $\mathrm{β}$-glucose. Propose a mechanism for isomerization.

The Wharton reaction converts an epoxy ketone to an allylic alcohol by reaction with hydrazine. Propose a mechanism. (Hint: Review the Wolff–Kishner reaction in Section 19-9.)

Draw structures corresponding to the following names:

1. Bromoacetone
2. (S)-2-Hydroxypropanal
3. 2-Methyl-3-heptanone
4. (2S,3R)-2,3,4-Trihydroxybutanal
5. 2,2,4,4-Tetramethyl-3-pentanone
6. 4-Methyl-3-penten-2-one
7. Butanedial
8. 3-Phenyl-2-propenal
9. 6,6-Dimethyl-2,4-cyclohexadienone
10. p-Nitroacetophenone

Draw and name the seven aldehydes and ketones with the formula ${\mathbf{C}}_5{\mathbf{H}}_{10}\mathbf{O}$ . Which are chiral?

Give IUPAC names for the following compounds:

(a)

(b)

(c)

(d)

(e)

(f)

Draw structures of compounds that fit the following descriptions:

1. An $\mathit{Î\pm }$,$\mathbf{β}$-unsaturated ketone, ${\mathbf{C}}_6{\mathbf{H}}_8\mathbf{O}$
2. An $\mathit{Î\pm }$-diketone
3. An aromatic ketone,${\mathbf{C}}_9{\mathbf{H}}_{10}\mathbf{O}$
4. A diene aldehyde,${\mathbf{C}}_7{\mathbf{H}}_8\mathbf{O}$

How would you use a Grignard reaction on an aldehyde or ketone to synthesize the following compounds?

1. 2-Pentanol
2. 1-Butanol
3. 1-Phenylcyclohexanol
4. Diphenylmethanol

How might you carry out the following selective transformations? One of the two schemes requires a protection step. (Recall from Section 19-4 that aldehydes are more reactive than ketones towards nucleophilic addition.)

b.