91Ó°ÊÓ

Rank the compounds in each of the following groups from strongest acid to weakest acid

Describe three ways to synthesize the following compound:

Show how 4-methyl-3-hexanol can be synthesised from 3-pentanone.

Show how the following compound can be synthesized from the given starting material.

Show how the following compounds can be prepared from cyclohexanone:

A $\mathrm{β},\mathrm{γ}$-unsaturated carbonyl compound rearranges to a more stable conjugated $\mathrm{Î\pm },\mathrm{β}$-unsaturated compound in the presence of either acid or base.

a. Propose a mechanism for the base- catalyzed rearrangement.

b. Propose a mechanism for the acid- catalyzed rearrangement.

$\mathrm{β},\mathrm{γ}$-unsaturated carbonyl compound $\mathrm{Î\pm },\mathrm{β}$-unsaturated carbonyl compound

Indicate how each of the following compounds can be synthesized from the given starting material and any other necessary reagents:

The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur. The organozinc reagent is prepared by treating an ß-bromo ester with zinc.

Describe how each of the following compounds can be prepared, using a Reformatsky reaction:

Explain why 92% of 2,4-pentanedione exists as the enol tautomer in hexane but only 15% of this compound exists as the enol tautomer in water.

Do a retrosynthetic analysis on each of the following compounds, ending with the given starting materials:

(a)

(b)