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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Chapter
Section
BuyFindarrow_forward

Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079
Textbook Problem

Which of the three compounds hexanal, 2-butanone, and 2-propanol will react with each of the following oxidizing or reducing agents? There may be more than one correct answer in a given situation.

  1. a. K2Cr2O7
  2. b. Tollens solution
  3. c. Benedict’s solution
  4. d. H2, Ni catalyst

(a)

Interpretation Introduction

Interpretation:

Among the three compounds which will react with K2Cr2O7 has to be given.

Concept Introduction:

In organic chemistry, oxidation reaction is referred to the number CO bonds increase and/or number of CH bonds decrease.

In organic chemistry, reduction reaction is referred to the number CO bonds decrease and/or number of CH bonds increase.

Alcohols undergo oxidation reaction and reduction reaction.  This depends upon the number of hydrogen atoms that is bonded to the alpha carbon atom.  Primary and secondary alcohol undergoes oxidation reaction while tertiary alcohol does not undergo oxidation reaction.  Primary alcohols undergo oxidation to give aldehyde and carboxylic acid as product.  Secondary alcohol undergoes oxidation to give ketone as the product.

Aldehyde undergoes oxidation to give carboxylic acid as the product while ketone does not undergo oxidation reaction.

The reverse of oxidation reaction is reduction reaction.  Reduction of aldehyde gives primary alcohol as the product and reduction of ketone gives secondary alcohol as the product.  Reduction can be accomplished using hydrogen gas and a metal catalyst namely nickel.

Explanation

Aldehyde undergoes oxidation reaction to give carboxylic acid as the product.  Alcohol undergoes oxidation reaction to give aldehyde or ketone as the product.  Ketone cannot be oxidized using oxidizing agent.

Given compounds are hexanal, 2-butanone and 2-propanol.  Among the given compounds, hexanal is an aldehyde, 2-butanone is a ketone and 2-propanol is an alcohol...

(b)

Interpretation Introduction

Interpretation:

The compounds that will react with the Tollen’s solution has to be identified.

Concept Introduction:

In organic chemistry, oxidation reaction is referred to the number CO bonds increase and/or number of CH bonds decrease.

In organic chemistry, reduction reaction is referred to the number CO bonds decrease and/or number of CH bonds increase.

Alcohols undergo oxidation reaction and reduction reaction.  This depends upon the number of hydrogen atoms that is bonded to the alpha carbon atom.  Primary and secondary alcohol undergoes oxidation reaction while tertiary alcohol does not undergo oxidation reaction.  Primary alcohols undergo oxidation to give aldehyde and carboxylic acid as product.  Secondary alcohol undergoes oxidation to give ketone as the product.

Aldehyde undergoes oxidation to give carboxylic acid as the product while ketone does not undergo oxidation reaction.

Tollen’s test:

This is also known as silver mirror test.  The reagent that is used in Tollen’s test is silver nitrate and ammonia in water.  Aldehyde reacts with Tollen’s reagent, where the silver ion is reduced to silver metal and the aldehyde is oxidized to carboxylic acid.

Organic And Biological Chemistry, Chapter 4, Problem 4.86EP , additional homework tip  1

Ketone does not undergo Tollen’s test to deposit silver metal.

(c)

Interpretation Introduction

Interpretation:

The compounds that will react with the Benedict’s solution has to be identified.

Concept Introduction:

In organic chemistry, oxidation reaction is referred to the number CO bonds increase and/or number of CH bonds decrease.

In organic chemistry, reduction reaction is referred to the number CO bonds decrease and/or number of CH bonds increase.

Alcohols undergo oxidation reaction and reduction reaction.  This depends upon the number of hydrogen atoms that is bonded to the alpha carbon atom.  Primary and secondary alcohol undergoes oxidation reaction while tertiary alcohol does not undergo oxidation reaction.  Primary alcohols undergo oxidation to give aldehyde and carboxylic acid as product.  Secondary alcohol undergoes oxidation to give ketone as the product.

Aldehyde undergoes oxidation to give carboxylic acid as the product while ketone does not undergo oxidation reaction.

Benedict’s test:

This test is also similar to Tollen’s test.  In this test, Cu2+ metal ion is used as oxidizing agent.  The Cu2+ ion is reduced to Cu+ ion while the aldehyde is oxidized to carboxylic acid.  Cu2O is precipitated as brick-red solid.  Ketone does not answer the Benedict’s test.  This is because ketone are not oxidized.

Organic And Biological Chemistry, Chapter 4, Problem 4.86EP , additional homework tip  2

(d)

Interpretation Introduction

Interpretation:

Among the three compounds which will react with H2, Ni catalyst has to be given.

Concept Introduction:

In organic chemistry, oxidation reaction is referred to the number CO bonds increase and/or number of CH bonds decrease.

In organic chemistry, reduction reaction is referred to the number CO bonds decrease and/or number of CH bonds increase.

Alcohols undergo oxidation reaction and reduction reaction.  This depends upon the number of hydrogen atoms that is bonded to the alpha carbon atom.  Primary and secondary alcohol undergoes oxidation reaction while tertiary alcohol does not undergo oxidation reaction.  Primary alcohols undergo oxidation to give aldehyde and carboxylic acid as product.  Secondary alcohol undergoes oxidation to give ketone as the product.

Aldehyde undergoes oxidation to give carboxylic acid as the product while ketone does not undergo oxidation reaction.

The reverse of oxidation reaction is reduction reaction.  Reduction of aldehyde gives primary alcohol as the product and reduction of ketone gives secondary alcohol as the product.  Reduction can be accomplished using hydrogen gas and a metal catalyst namely nickel.

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