2 NaH CN O C13H16N2 phenylacetonitrile meperidine

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter20: Carbohydrates
Section: Chapter Questions
Problem 20.74P
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A key step in the synthesis of the narcotic analgesic meperidine (trade
name Demerol) is the conversion of phenylacetonitrile to X. (a) What is
the structure of X? (b) What reactions convert X to meperidine ?

2 NaH
CN
O
C13H16N2
phenylacetonitrile
meperidine
Transcribed Image Text:2 NaH CN O C13H16N2 phenylacetonitrile meperidine
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The total transformation mechanism is given below - 

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