13. Alcohols and Carbonyl Compounds

Predict the products of the reactions of the following compounds with:

1. chromic acid or excess sodium hypochlorite with acetic acid.

2. PCC or NaOCl (1 equivalent) with TEMPO.

g. hexan-1-ol

h. acetaldehyde, CH₃CHO

Fill in each box with the appropriate reagent:

a.

Lipoic acid is often found near the active sites of enzymes, usually bound to the peptide by a long, flexible amide linkage with a lysine residue.

(a) Is lipoic acid a mild oxidizing agent or a mild reducing agent? Draw it in both its oxidized and reduced forms.

(b) Show how lipoic acid might react with two Cys residues to form a disulfide bridge.

(c) Give a balanced equation for the hypothetical oxidation or reduction, as you predicted in part (a), of an aldehyde by lipoic acid.

Fill in the missing reactant, reagent, or product for each of the following oxidation reactions.

(c)

Fill in the missing reactant, reagent, or product for each of the following oxidation reactions.

(f)

Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.

(d)

Write the appropriate reagent over each arrow.

Predict the reagents or reactant(s) necessary to complete the following syntheses.

(a)

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(c) but-2-enal → but-2-enoic acid

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.

(e) p-xylene → terephthalic acid