ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
2nd Edition
ISBN: 9781118872925
Author: Klein
Publisher: JOHN WILEY+SONS INC.CUSTOM
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Question
Chapter 9.6, Problem 18CC
Interpretation Introduction
Interpretation:
Structure of compound A should be predicted according to the given reaction condition.
Concept introduction:
Hydroboration-oxidation reaction: addition of water molecule across the double bond in anti-Markovnikov’s path is known as hydroboration oxidation process. In this reaction used reagent is borane in THF solvent followed by hydrogen peroxide, which is used for oxidation purpose.
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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
Identify the unknown compound from its IR and proton NMR spectra.
C4H6O:
'H NMR: 82.43 (1H, t, J = 2 Hz); 8 3.41 (3H, s); 8 4.10 (2H, d, J = 2 Hz)
IR: 2125, 3300 cm¹
The C4H6O compound liberates a gas when treated with C2H5 MgBr.
Draw the unknown compound.
Select
Draw
с
H
Templates
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Chapter 9 Solutions
ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
Ch. 9.3 - Prob. 3PTSCh. 9.3 - Prob. 4ATSCh. 9.3 - Prob. 5ATSCh. 9.3 - Prob. 2LTSCh. 9.3 - Prob. 7PTSCh. 9.3 - Prob. 8ATSCh. 9.3 - Prob. 9ATSCh. 9.4 - Prob. 10CCCh. 9.4 - Prob. 11CCCh. 9.4 - Prob. 3LTS
Ch. 9.4 - Prob. 12PTSCh. 9.4 - Prob. 13ATSCh. 9.4 - Prob. 14ATSCh. 9.6 - Prob. 18CCCh. 9.6 - Prob. 4LTSCh. 9.6 - Prob. 19PTSCh. 9.6 - Prob. 20ATSCh. 9.6 - Prob. 21ATSCh. 9.6 - Prob. 22ATSCh. 9.7 - Prob. 23PTSCh. 9.7 - Prob. 24ATSCh. 9.7 - Prob. 25ATSCh. 9.8 - Prob. 26CCCh. 9.8 - Prob. 27PTSCh. 9.8 - Prob. 28ATSCh. 9.8 - Prob. 29ATSCh. 9.9 - Prob. 30PTSCh. 9.9 - Prob. 31ATSCh. 9.9 - Prob. 32ATSCh. 9.10 - Prob. 33CCCh. 9.11 - Prob. 34PTSCh. 9.11 - Prob. 35ATSCh. 9.12 - Prob. 9LTSCh. 9.12 - Prob. 36PTSCh. 9.12 - Prob. 37ATSCh. 9.12 - Prob. 38ATSCh. 9.12 - Prob. 39ATSCh. 9.13 - Prob. 10LTSCh. 9.13 - Prob. 40PTSCh. 9.13 - Prob. 41ATSCh. 9.13 - Prob. 11LTSCh. 9.13 - Prob. 42PTSCh. 9.13 - Prob. 43ATSCh. 9.13 - Prob. 44ATSCh. 9.13 - Prob. 12LTSCh. 9.13 - Prob. 47ATSCh. 9 - Prob. 48PPCh. 9 - Prob. 49PPCh. 9 - Prob. 50PPCh. 9 - Prob. 51PPCh. 9 - Prob. 52PPCh. 9 - Prob. 53PPCh. 9 - Prob. 54PPCh. 9 - Prob. 55PPCh. 9 - Prob. 56PPCh. 9 - Prob. 59PPCh. 9 - Prob. 60PPCh. 9 - Prob. 61PPCh. 9 - Prob. 62PPCh. 9 - Prob. 63PPCh. 9 - Prob. 64PPCh. 9 - Prob. 65PPCh. 9 - Prob. 66PPCh. 9 - Prob. 67PPCh. 9 - Prob. 68PPCh. 9 - Prob. 69PPCh. 9 - Prob. 70PPCh. 9 - Prob. 71PPCh. 9 - Prob. 72PPCh. 9 - Prob. 73PPCh. 9 - Prob. 74IPCh. 9 - Prob. 75IPCh. 9 - Prob. 76IPCh. 9 - Prob. 77IPCh. 9 - Prob. 78IPCh. 9 - Prob. 79IPCh. 9 - Prob. 80IPCh. 9 - Prob. 81IPCh. 9 - Prob. 82IPCh. 9 - Prob. 83IP
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