Classify each reaction as an oxidation, a reduction, or neither.

(a)

(b)

(c)

Classify each reaction as an oxidation, a reduction, or neither.

(d)

(e)

(f)

Classify each reaction as an oxidation, a reduction, or neither.

(g)

(h)

(i)

Classify each reaction as an oxidation, a reduction, or neither.

(j)

(k)

(l)

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

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.

d. cyclohexanone

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.

e. cyclohexane

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.

f. 1-phenylpropan-1-ol

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

We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the Lewis structures of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation?

a. the Cr in chromic acid

b. the Cl in sodium hypochlorite

c. the S in the Swern oxidation

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na₂Cr₂O₇/H₂SO₄, (2) PCC, (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

a. octan-1-ol

b. octan-3-ol

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na₂Cr₂O₇/H₂SO₄, (2) PCC

c. 4-hydroxydecanal

Give the structure of the principal product(s) when each of the following alcohols reacts with (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

c. 4-hydroxydecanal

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na₂Cr₂O₇/H₂SO₄, (2) PCC

d. 1-methylcyclohexan-1,4-diol