Q2P Predict the products of the reac... [FREE SOLUTION]

Chapter 11: Q2P (page 547)

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.
(a)cyclohexanol (b)1-methylcyclohexanol
(c)cyclopentylmethanol (d)cyclohexanone
(e)cyclohexane (f)1-phenylpropan-1-ol
(g)hexan-1-ol (h)acetaldehyde, CH₃CHO

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The use of NaOCl and TEMPO as the reagent for oxidation

Primary alcohols get oxidized to aldehydes using sodium hypochlorite(NaOCl) with TEMPO. The use of the excess of reagent NaOCl with TEMPO can oxidize alcohols into carboxylic acids.

The use of chromic acid as the reagent for oxidation

Primary alcohols can be converted into aldehydes by using pyridinium chlorochromate (PCC) as the reagent. Secondary alcohols can also be oxidized to ketones using this reagent.

Products formed when the given starting material undergoes oxidation with the given reagents

(a)The reaction of cyclohexanol with PCC or NaOCl, TEMPO and H₂CrO₄ or NaOCl/HOAc produces cyclohexanone as the product. The reaction can be given as:

Reaction of cyclohexanol with various reagents

(b)The reaction of 1-methyl cyclohexanol with PCC or NaOCl, TEMPO and H₂CrO₄ or NaOCl/HOAc creates no products. The reaction can be given as:

Reaction of 1-methylcyclohexanol with various reagents

(c)The reaction of cyclopentylmethanol with PCC or NaOCl, TEMPO produces cyclopentanal as the product. Cyclopentylmethanol reacts with H₂CrO₄ or NaOCl/HOAc creating cyclopentanoic acid as the product. The reaction can be given as:

Reaction of cyclopentylmethanol with various reagents

(d) The reaction of cyclohexanone with PCC or NaOCl, TEMPO and H₂CrO₄ or NaOCl/HOAc creates no products. The reaction can be given as:

Reaction of cyclohexanone with various reagents

(e) The reaction of cyclohexane with PCC or NaOCl, TEMPO and H₂CrO₄ or NaOCl/HOAc creates no products. The reaction can be given as:

Reaction of cyclohexane with various reagents

(f)1-phenylpropan-1-ol with PCC or NaOCl, TEMPO and H₂CrO₄ or NaOCl/HOAc generates 1-phenylpropan-1-one as the product.

Reaction of 1-phenylpropan-1-ol with various reagents

(g)Hexan-1-ol with PCC or NaOCl, TEMPO generates hexan-1-one as the product. The treatment of Hexan-1-ol with H₂CrO₄ or NaOCl/HOAc generates hexan-1-oic acid as the product. The reaction can be given as:

Reaction of Hexan-1-ol with various reagents

(h)The reaction of acetaldehyde with PCC produces no products. The reaction of acetaldehyde with NaOCl/TEMPO generates ethanoic acid as the product. Acetaldehyde reacts with H₂CrO₄ or NaOCl/HOAc generating ethanoic acid as the product. The reaction can be given as: