ORGANIC CHEMISTRY (LL) >CUSTOM PACKAGE<
4th Edition
ISBN: 9781119838791
Author: Klein
Publisher: WILEY
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Chapter 17, Problem 67IP
Interpretation Introduction
Interpretation: For the given transformation an efficient synthesis should be proposed.
Concept introduction:
- When approaching a synthesis problem two questions should be asked
-
- 1. Is there a change in the carbon skeleton?
- 2. Is there a change in the position or identity of the
functional group
- When approaching a synthesis problem, should not encounter a one-step method
- The desired transformation can achieve in two steps
- There are two ways to introduce functionality at a benzylic position
-
- 1. Oxidation, which produces benzoic acid at benzylic position
- 2. Radical bromination, which produces benzylic halide.
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When an unknown amine reacts with an unknown acid chloride, an amide with a molecular mass of 163 g/mol (M* = 163 m/z)
is formed. In the infrared spectrum, important absorptions appear at 1661, 750 and 690 cm. The 13C NMR and DEPT spectra
are provided. Draw the structure of the product as the resonance contributor lacking any formal charges.
13C NMR
DEPT 90
200
160
120
80
40
0
200
160
120
80
40
0
DEPT 135
T
200
160
120
80
40
0
Draw the unknown amide.
Select
Dow
Templates
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Frage
Chapter 17 Solutions
ORGANIC CHEMISTRY (LL) >CUSTOM PACKAGE<
Ch. 17.2 - Prob. 1LTSCh. 17.2 - Prob. 1PTSCh. 17.2 - Prob. 2PTSCh. 17.2 - Prob. 3PTSCh. 17.2 - Prob. 4PTSCh. 17.4 - Prob. 6CCCh. 17.4 - Prob. 8CCCh. 17.4 - Prob. 9CCCh. 17.5 - Prob. 10CCCh. 17.5 - Prob. 2LTS
Ch. 17.5 - Prob. 11PTSCh. 17.5 - Prob. 12ATSCh. 17 - Prob. 24PPCh. 17 - Prob. 25PPCh. 17 - Prob. 26PPCh. 17 - Prob. 27PPCh. 17 - Prob. 28PPCh. 17 - Prob. 29PPCh. 17 - Prob. 30PPCh. 17 - Prob. 31PPCh. 17 - Prob. 32PPCh. 17 - Prob. 33PPCh. 17 - Prob. 34PPCh. 17 - Prob. 35PPCh. 17 - Prob. 36PPCh. 17 - Prob. 37PPCh. 17 - Prob. 38PPCh. 17 - Prob. 55IPCh. 17 - Prob. 56IPCh. 17 - Prob. 57IPCh. 17 - Prob. 58IPCh. 17 - Prob. 59IPCh. 17 - Prob. 60IPCh. 17 - Prob. 61IPCh. 17 - Prob. 62IPCh. 17 - Prob. 63IPCh. 17 - Prob. 64IPCh. 17 - Prob. 65IPCh. 17 - Prob. 66IPCh. 17 - Prob. 67IP
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