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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

Short Answer

Expert verified

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.

Step by step solution

01

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.

02

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.

03

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:

Reaction of acetaldehyde with various reagents

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Most popular questions from this chapter

Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation usingand pyridine, followed by elimination using KOC(CH3)3as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanol eliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.

Show how you would synthesize the following compound. As starting materials, you may use any alcohols containing five or fewer carbon atoms and any necessary solvents and inorganic reagents.

Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBr3, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4 dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.

Show how you would use a simple chemical test to distinguish between the following pairs of compounds. Tell what you would observe with each compound.

(a)isopropyl alcohol andtert-butyl alcohol

(b)isopropyl alcohol and butan-2-one, CH3COCH2CH3

(c)hexan-1-ol and cyclohexanol

(d)allyl alcohol and propan-1-ol

(e)butan-2-one andtert-butyl alcohol

The compound shown below has three different types of OH groups, all with different acidities. Show the structure produced after this compound is treated with different amounts of NaH followed by a methylating reagent. Add a brief explanation.

(a)1 equivalent of NaH, followed by 1 equivalent of CH3l and heat

(b)2 equivalents of NaH, followed by 2 equivalents of CH3l and heat

(c) 3 equivalents of NaH, followed by 3 equivalents of CH3l and heat
See all solutions

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