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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

Draw the structural formula of the organic product or indicate that no reaction occurs for the following situations.

  1. a. Butanal in the Tollens test
  2. b. 2-Butanone in the Tollens test
  3. c. 3-Methylpentanal in the Benedict’s test
  4. d. 3-Pentanone in the Benedict’s test

(a)

Interpretation Introduction

Interpretation:

Structural formula of the organic product formed when butanal undergoes Tollen’s test has to be drawn.

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 4.77EP , additional homework tip  1

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

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 4.77EP , additional homework tip  2

Explanation

Aldehydes undergo Tollen’s test.  The product formed when aldehyde undergo oxidation is a carboxylic acid.  The general oxidation reaction for aldehyde can be given as,

Given aldehyde is butanal and the structure can be given as shown below,

(b)

Interpretation Introduction

Interpretation:

Structural formula of the organic product formed when 2-butanone undergoes Tollen’s test has to be drawn.

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 4.77EP , additional homework tip  3

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

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 4.77EP , additional homework tip  4

(c)

Interpretation Introduction

Interpretation:

Structural formula of the organic product formed when 3-methylpentanal undergoes Benedict’s test has to be drawn.

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 4.77EP , additional homework tip  5

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

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 ketones are not oxidized.

Organic And Biological Chemistry, Chapter 4, Problem 4.77EP , additional homework tip  6

(d)

Interpretation Introduction

Interpretation:

Structural formula of the organic product formed when 3-pentanone undergoes Benedict’s test has to be drawn.

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 4.77EP , additional homework tip  7

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

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 ketones are not oxidized.

Organic And Biological Chemistry, Chapter 4, Problem 4.77EP , additional homework tip  8

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