ORGANIC CHEMISTRY-PRINT COMPANION (LL)
ORGANIC CHEMISTRY-PRINT COMPANION (LL)
3rd Edition
ISBN: 9781119444251
Author: Klein
Publisher: WILEY
Question
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Chapter 26, Problem 29PP

a)

Interpretation Introduction

Interpretation:

The products need to be predicted when tripalmitolein is treated with the given set of reagents.

Concept introduction:

Reduction is a reaction in which hydrogen is added to the given compound.  One of the examples is conversion of unsaturated bonds to saturated bonds.

To predict: the product formed when tripalmitolein is treated with excess hydrogen and nickel.

a)

Expert Solution
Check Mark

Answer to Problem 29PP

Solution:

The product predicted when tripalmitolein is treated with hydrogen and nickel is,

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 26, Problem 29PP , additional homework tip  1

Explanation of Solution

Structure of tripalmitolein

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 26, Problem 29PP , additional homework tip  2

The structure of tripalmitolein is drawn as above.  In tripalmitolein there are three double bonds.

Reaction with excess hydrogen and nickel.

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 26, Problem 29PP , additional homework tip  3

When tripalmitolein is treated with excess hydrogen and nickel, all the double bonds present in the fatty acid residue are reduced to saturated bonds to give a saturated triglyceride as shown above.

Conclusion

The product formed when tripalmitolein undergoes reaction with excess hydrogen and nickel is a saturated triglyceride and the structure is,

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 26, Problem 29PP , additional homework tip  4

(b)

Interpretation Introduction

Interpretation:

The products need to be predicted when tripalmitolein is treated with the given set of reagents.

Concept introduction:

When triglyceride is treated with aqueous sodium hydroxide, the ester group is hydrolyzed to give glycerol and the fatty acid as carboxylate ion.

To predict: the product formed when tripalmitolein is treated with aqueous sodium hydroxide.

(b)

Expert Solution
Check Mark

Answer to Problem 29PP

Answer

The product obtained when tripalmitolein is treated with aqueous base is,

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 26, Problem 29PP , additional homework tip  5

Explanation of Solution

Structure of tripalmitolein

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 26, Problem 29PP , additional homework tip  6

The structure of tripalmitolein is drawn as above.  In tripalmitolein there are three ester groups.

Reaction with excess hydrogen and nickel.

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 26, Problem 29PP , additional homework tip  7

When tripalmitolein is treated with aqueous sodium hydroxide the ester group is hydrolyzed to form glycerol and fatty acid carboxylate ion.

Conclusion

The product formed when tripalmitolein is treated with aqueous sodium hydroxide is glycerol and three equivalents of carboxylate ion,

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 26, Problem 29PP , additional homework tip  8

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