EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 17, Problem 17.33AP
Interpretation Introduction
Interpretation:
The compounds A, B and C are to be identified.
Concept introduction:
Primary and secondary alcohols can be oxidized into
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Structure of
product C
A hydrocarbon, A, with formula C11H16
undergoes hydrogenation with Pd to give
product B, C11H22, and with Lindlar's
catalyst to give product C, C11 H18.
Ozonolysis leads to a mixture of
products including cyclohexanone and
4-oxobutanoic acid. Treatment with
sodium amide (NaNH2) followed by
bromoethane gives compound D, C13H20.
Draw possible structures for A, B, C, and
D.
H₂,
Lindlar's
Problem 13 of 14
Structure of
A
1. NaNH2
Submit
2.
CH3CH₂Br
Structure of
product D
Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.
Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized.
Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.
Chapter 17 Solutions
EBK ORGANIC CHEMISTRY
Ch. 17 - Prob. 17.1PCh. 17 - Prob. 17.2PCh. 17 - Prob. 17.3PCh. 17 - Prob. 17.4PCh. 17 - Prob. 17.5PCh. 17 - Prob. 17.6PCh. 17 - Prob. 17.7PCh. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Prob. 17.14PCh. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Prob. 17.22APCh. 17 - Prob. 17.23APCh. 17 - Prob. 17.24APCh. 17 - Prob. 17.25APCh. 17 - Prob. 17.26APCh. 17 - Prob. 17.27APCh. 17 - Prob. 17.28APCh. 17 - Prob. 17.29APCh. 17 - Prob. 17.30APCh. 17 - Prob. 17.31APCh. 17 - Prob. 17.32APCh. 17 - Prob. 17.33APCh. 17 - Prob. 17.35APCh. 17 - Prob. 17.36APCh. 17 - Prob. 17.37APCh. 17 - Prob. 17.38APCh. 17 - Prob. 17.39APCh. 17 - Prob. 17.40APCh. 17 - Prob. 17.41APCh. 17 - Prob. 17.42APCh. 17 - Prob. 17.43APCh. 17 - Prob. 17.44APCh. 17 - Prob. 17.45APCh. 17 - Prob. 17.46APCh. 17 - Prob. 17.47APCh. 17 - Prob. 17.48APCh. 17 - Prob. 17.49APCh. 17 - Prob. 17.50APCh. 17 - Prob. 17.51APCh. 17 - Prob. 17.52APCh. 17 - Prob. 17.53APCh. 17 - Prob. 17.54APCh. 17 - Prob. 17.55APCh. 17 - Prob. 17.56APCh. 17 - Prob. 17.57APCh. 17 - Prob. 17.58APCh. 17 - Prob. 17.59AP
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