Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 20, Problem 34P

a)

Interpretation Introduction

Interpretation:

The product obtained when D-galactose reacts with nitric acid is to be stated.

Concept Introduction:

D-galactose is a monosaccharide molecule and it is sweet in taste as glucose.  It is C-4 epimer of glucose.

Epimers are pair of stereoisoisomers which differ in configuration at one stereogenic center.  In D-galactose molecule one terminal aldehydic and one terminal alcoholic group is present.

Nitric acid has the chemical formula HNO3 and behaves as a good oxidizing agent. It oxidizes both the terminal functional groups in the acidic group.

a)

Expert Solution
Check Mark

Answer to Problem 34P

The product obtained when D-galactose reacts with nitric acid is given below,

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  1

Figure 1

Explanation of Solution

The product obtained when D-galactose reacts with nitric acid is as follows,

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  2

Figure 1

HNO3 oxidizes D-galactose to D-galactaric acid.

b)

Interpretation Introduction

Interpretation:

The product obtained when D-galactose reacts with Ag+,NH3,OH is to be stated.

Concept Introduction:

D-galactose is a monosaccharide molecule and it is sweet in taste as glucose. It is C-4 epimer of glucose.

Epimers are pair of stereoisoisomers which differ in configuration at one stereogenic center.  In D-galactose molecule one terminal aldehydic and one terminal alcoholic group is present.  The given ions Ag+,NH3,OH are the reactants and gives diamine silver complex.  This complex reacts with D-galactose.  It gives D-galactonic acid.

b)

Expert Solution
Check Mark

Answer to Problem 34P

The product obtained when D-galactose reacts with Ag+,NH3,OH is given below in Figure 2.

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  3

Figure 2

Explanation of Solution

The product obtained when D-galactose reacts with Ag+,NH3,OH is as follows,

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  4

Figure 2

The given ions Ag+,NH3,OH are the reactants and gives diamine silver complex. This complex reacts with D-galactose.  It gives D-galactonic acid.

c)

Interpretation Introduction

Interpretation:

The product obtained when D-galactose reacts with NaBH4, followed by H3O+ is to be stated.

Concept Introduction:

D-galactose is a monosaccharide molecule and it is sweet in taste as glucose.  It is C-4 epimer of glucose.

Epimers are pair of stereoisoisomers which differ in configuration at one stereogenic center.  In D-galactose molecule one terminal aldehydic and one terminal alcoholic group is present.  NaBH4 is a good reducing agent.  It reduces aldehydic group to the alcoholic group in the presence of H3O+.

c)

Expert Solution
Check Mark

Answer to Problem 34P

The product obtained when D-galactose reacts with NaBH4, followed by H3O+ is given in Figure 3.

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  5

Figure 3

Explanation of Solution

The product obtained when D-galactose reacts with NaBH4, followed by H3O+ is as follows,

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  6

Figure 3

The product obtained when D-galactose reacts with NaBH4, followed by hydrolysis in acidic medium is D-galacitol.

d)

Interpretation Introduction

Interpretation:

The product obtained when D-galactose reacts with excess CH3I and Ag2O is to be stated.

Concept Introduction:

D-galactose is a monosaccharide molecule and it is sweet in taste as glucose. It is C-4 epimer of glucose.  Epimers are pair of stereoisoisomers which differ in configuration at one stereogenic center.  In D-galactose molecule one terminal aldehydic and one terminal alcoholic group is present.

d)

Expert Solution
Check Mark

Answer to Problem 34P

The product obtained when D-galactose reacts with excess CH3I and Ag2O is given in Figure 4.

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  7

Figure 4

Explanation of Solution

The product obtained when D-galactose reacts with excess CH3I and Ag2O is as follows,

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  8

Figure 4

e)

Interpretation Introduction

Interpretation:

The product obtained when D-galactose reacts with Br2 in water is to be stated.

Concept Introduction:

D-galactose is a monosaccharide molecule and it is sweet in taste as glucose.  It is C-4 epimer of glucose.  Epimers are pair of stereoisoisomers which differ in configuration at one stereogenic center.  In D-galactose molecule one terminal aldehydic and one terminal alcoholic group is present.

e)

Expert Solution
Check Mark

Answer to Problem 34P

The product obtained when D-galactose reacts with Br2 in water is given in Figure 5.

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  9

Figure 5

Explanation of Solution

The product obtained when D-galactose reacts with Br2 in water is as follows,

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  10

Figure 5

f)

Interpretation Introduction

Interpretation:

The product obtained when D-galactose reacts with ethanol +HCl is to be stated.

Concept Introduction:

D-galactose is a monosaccharide molecule and it is sweet in taste as glucose.  It is C-4 epimer of glucose.  Epimers are pair of stereoisoisomers which differ in configuration at one stereogenic center.  In D-galactose molecule one terminal aldehydic and one terminal alcoholic group is present.

f)

Expert Solution
Check Mark

Answer to Problem 34P

The product obtained when D-galactose reacts with ethanol +HCl is given in Figure 6.

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  11

Figure 6

Explanation of Solution

The product obtained when D-galactose reacts with ethanol +HCl is as follows,

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  12

Figure 6

g)

Interpretation Introduction

Interpretation:

The products obtained when D-galactose reacts with the given reactants are to be stated.

Concept Introduction:

D-galactose is a monosaccharide molecule and it is sweet in taste as glucose.  It is C-4 epimer of glucose.  Epimers are pair of stereoisoisomers which differ in configuration at one stereogenic center.  In D-galactose molecule one terminal aldehydic and one terminal alcoholic group is present.

g)

Expert Solution
Check Mark

Answer to Problem 34P

The products obtained when D-galactose reacts with the given reactants are shown in figure 7.

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  13

Figure 7

Explanation of Solution

The given reactants are hydroxylamine/trace acid, acetic anhydride/heat and OH-/H2O. All these reactants are used in a sequence and it is shown as,

Organic Chemistry (8th Edition), Chapter 20, Problem 34P , additional homework tip  14

Figure 7

In the above reaction D-galactose first reacts with hydroxylamine in the presence of an acid, a compound of oxime is formed.  Then it reacts with acetic anhydride with heat gives nitrile compound.  Now, nitrile compound undergoes a reaction with base a compound D-Lyxose is formed.

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Students have asked these similar questions
What would be the product if D-talose is reacted with:1. NH2OH then (CH3CO)2O, NaOCOCH3 then NaOCH3, then HNO3, H2O [note this is a consectutive reaction] 2. oxidation using HNO3
What would be the product if D-galactose is react with1. NH2OH then (CH3CO)2O, NaOCOCH3 then NaOCH3, then HNO3, H2O [note this is a consectutive reaction] 2. oxidation using HNO3
What would be the product if D-allose is reacted witha.. 1.) NH2OH then 2.) (CH3CO)2O, NaOCOCH3 then 3.)NaOCH3, then 4.)HNO3, H2O [note this is a consectutive reaction] b. oxidation using HNO3

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