Organic Chemistry
Organic Chemistry
3rd Edition
ISBN: 9781119338352
Author: Klein
Publisher: WILEY
Question
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Chapter 24.6, Problem 34CC

(a)

Interpretation Introduction

Interpretation:

For the each given compounds, the name and structure of the product formed when they undergoes Kiliani-Fischer synthesis should be determined.

Concept introduction:

  • Aldopentose produces two aldohexoses through Kiliani-Fischer synthesis (chain lengthening process).
  • In Kiliani-Fischer synthesis, sugar reacts with aqueous cyanide (NaCN); the cyanide undergoes nucleophilic addition to the carbonyl group of the sugar which yields cynohydrine. The resulting cyanohydrin is heated with water, which undergoes hydrolysis and forms carboxylic acid. These carboxylic acids react itself and form more stable lactones. Further, lactone is undergoes reduction reaction with a sodium amalgam which yields two aldohexoses.

(b)

Interpretation Introduction

Interpretation:

For the each given compounds, the name and structure of the product formed when they undergoes Kiliani-Fischer synthesis should be determined.

Concept introduction:

  • Aldopentose produces two aldohexoses through Kiliani-Fischer synthesis (chain lengthening process).
  • In Kiliani-Fischer synthesis, sugar reacts with aqueous cyanide (NaCN); the cyanide undergoes nucleophilic addition to the carbonyl group of the sugar which yields cynohydrine. The resulting cyanohydrin is heated with water, which undergoes hydrolysis and forms carboxylic acid. These carboxylic acids react itself and form more stable lactones. Further, lactone is undergoes reduction reaction with a sodium amalgam which yields two aldohexoses.

(c)

Interpretation Introduction

Interpretation:

For the each given compounds, the name and structure of the product formed when they undergoes Kiliani-Fischer synthesis should be determined.

Concept introduction:

  • Aldopentose produces two aldohexoses through Kiliani-Fischer synthesis (chain lengthening process).
  • In Kiliani-Fischer synthesis, sugar reacts with aqueous cyanide (NaCN); the cyanide undergoes nucleophilic addition to the carbonyl group of the sugar which yields cynohydrine. The resulting cyanohydrin is heated with water, which undergoes hydrolysis and forms carboxylic acid. These carboxylic acids react itself and form more stable lactones. Further, lactone is undergoes reduction reaction with a sodium amalgam which yields two aldohexoses.

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Chapter 24 Solutions

Organic Chemistry

Ch. 24.5 - Prob. 10ATSCh. 24.5 - Prob. 11ATSCh. 24.5 - Prob. 2LTSCh. 24.5 - Prob. 12PTSCh. 24.5 - Prob. 13PTSCh. 24.5 - Prob. 14ATSCh. 24.5 - Prob. 15ATSCh. 24.5 - Prob. 3LTSCh. 24.5 - Prob. 16PTSCh. 24.5 - Prob. 17ATSCh. 24.5 - Prob. 18ATSCh. 24.5 - Prob. 19CCCh. 24.5 - Prob. 20CCCh. 24.5 - Prob. 21CCCh. 24.5 - Prob. 22CCCh. 24.6 - Prob. 23CCCh. 24.6 - Prob. 24CCCh. 24.6 - Prob. 25CCCh. 24.6 - Prob. 26CCCh. 24.6 - Prob. 27CCCh. 24.6 - Prob. 28CCCh. 24.6 - Prob. 29CCCh. 24.6 - Prob. 30CCCh. 24.6 - Prob. 4LTSCh. 24.6 - Prob. 31PTSCh. 24.6 - Prob. 32ATSCh. 24.6 - Prob. 33ATSCh. 24.6 - Prob. 34CCCh. 24.6 - Prob. 35CCCh. 24.6 - Prob. 36CCCh. 24.6 - Prob. 37CCCh. 24.6 - Prob. 38CCCh. 24.7 - Prob. 5LTSCh. 24.7 - Prob. 39PTSCh. 24.7 - Prob. 40ATSCh. 24.7 - Prob. 41CCCh. 24 - Prob. 42PPCh. 24 - Prob. 43PPCh. 24 - Prob. 44PPCh. 24 - Prob. 45PPCh. 24 - Prob. 46PPCh. 24 - Prob. 47PPCh. 24 - Prob. 48PPCh. 24 - Prob. 49PPCh. 24 - Prob. 50PPCh. 24 - Prob. 51PPCh. 24 - Prob. 52PPCh. 24 - Prob. 53PPCh. 24 - Prob. 54PPCh. 24 - Prob. 55PPCh. 24 - Prob. 56PPCh. 24 - Prob. 57PPCh. 24 - Prob. 58PPCh. 24 - Prob. 59PPCh. 24 - Prob. 60PPCh. 24 - Prob. 61PPCh. 24 - Prob. 62PPCh. 24 - Prob. 63PPCh. 24 - Prob. 64PPCh. 24 - Prob. 65PPCh. 24 - Prob. 66PPCh. 24 - Prob. 67PPCh. 24 - Prob. 68PPCh. 24 - Prob. 69PPCh. 24 - Prob. 70PPCh. 24 - Prob. 71PPCh. 24 - Prob. 72PPCh. 24 - Prob. 73PPCh. 24 - Prob. 74PPCh. 24 - Prob. 75PPCh. 24 - Prob. 76PPCh. 24 - Prob. 77PPCh. 24 - Prob. 78PPCh. 24 - Prob. 79PPCh. 24 - Prob. 80PPCh. 24 - Prob. 81IPCh. 24 - Prob. 82IPCh. 24 - Prob. 83IPCh. 24 - Prob. 84IPCh. 24 - Prob. 85IPCh. 24 - Prob. 86IPCh. 24 - Prob. 87CPCh. 24 - Prob. 88CPCh. 24 - Prob. 89CP
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