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Chapter 17: Q14P (page 552)

What alcohols would give the following products on oxidation?

(a)

(b)

(c)

Short Answer

Expert verified

a.

b.

c.

Step by step solution

01

Oxidation of alcohol

The oxidation of alcohol gives carbonyl-containing compounds like aldehyde, ketone, and carboxylic acid.From primary (1o) alcohol, aldehyde or carboxylic acid is formed. From secondary (2o) alcohol, a ketone is formed. But oxidation of tertiary alcohols does not occur because they do not react much with oxidizing agents.

02

The alcohol needed to produce the product (a) 

a.

The given product is a ketone, and the alcohol needed for oxidation is secondary. We know that secondary alcohols yield ketones. Here, the reagent used for oxidation is CrO3/H3O+.



Oxidation of alcohol

03

The alcohol needed to produce the product (b) 

b.

The given product is an aldehyde, and the alcohol needed for oxidation is a primary alcohol. We know that primary alcohol on oxidation using Periodinane/ CH2Cl2gives an aldehyde.


Oxidation of alcohol

04

The alcohol needed to produce the product (c) 

c.

The given product is a cyclopentanone (ketone), and the alcohol needed for oxidation is cyclopentanol (secondary alcohol). So, when cyclopentanol is treated with CrO3/H3O+, the product formed is cyclopentanone because secondary alcohols yield ketones.



Oxidation of alcohol

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Most popular questions from this chapter

Draw and name the eight isomeric alcohols with the formula C5H12O

Question: How would you prepare the following compounds from

2-phenylethanol?

More than one step may be required.

(a) StyrenePhCH=CH2

(b) PhenylacetaldehydePhCH2CHO

(c) Phenylacetic acidPhCH2CO2H

(d) Benzoic acid

(e) Ethylbenzene

(f) Benzaldehyde

(g) 1-Phenylethanol

(h) 1-Bromo-2-phenylethane

For each reaction, write the mechanism using curved arrows for the conversion of the alcohol into the corresponding alkene with POCl3. In each case, explain the regiochemistry of the elimination.

(a)

(b)

(c)

The following data for isomeric four-carbon alcohols show that there is a decrease in boiling point with increasing substitution of the OH-bearing carbon. How might you account for this trend?

1-Butanol, bp 117.5oC

2-Butanol, bp 99.5oC

2-Methyl-2-propanol, bp 82.2oC

Which of the eight alcohols that you identified in Problem 17-38 react with CrO3 in aqueous acid? Show the products you would expect from each reaction
See all solutions

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