ORGANIC CHEMISTRY,SOLNS...-ETEXT+BOX
4th Edition
ISBN: 9781119760702
Author: Klein
Publisher: WILEY
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Question
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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ORGANIC CHEMISTRY,SOLNS...-ETEXT+BOX
Ch. 24.2 - Prob. 1CCCh. 24.2 - Prob. 2CCCh. 24.2 - Prob. 3CCCh. 24.2 - Prob. 4CCCh. 24.2 - Prob. 5CCCh. 24.2 - Prob. 6CCCh. 24.4 - Prob. 7CCCh. 24.4 - Prob. 8CCCh. 24.5 - Prob. 1LTSCh. 24.5 - Prob. 9PTS
Ch. 24.5 - Prob. 2LTSCh. 24.5 - Prob. 12PTSCh. 24.5 - Prob. 13PTSCh. 24.5 - Prob. 3LTSCh. 24.5 - Prob. 16PTSCh. 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. 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. 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. 86IPCh. 24 - Prob. 87IPCh. 24 - Prob. 88IPCh. 24 - Prob. 89IP
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