EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 16, Problem 16.54AP
Interpretation Introduction
Interpretation:
The structure of the product with formula
Concept introduction:
An electrophile is a positive species which has an affinity towards negative charge and a nucleophile is a negative species which has an affinity towards a positive charge.
In an electrophilic addition reaction, there is an addition of an electrophilic reagent on a nucleophilic group. The double bond and triple bond containing compounds act as a nucleophile. The addition of electrophilic reagent on nucleophilic compound leads to the dissociation of electrons and formation of two bonds.
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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
In the following sequence of reactions which products are identified correctly?
Compound A (C 7H 11B1) is treated with magnesium in ether to give B (C 7H 11MgBr), which reacts violently with D 20 to give 1-methylcyclohexene
B with acetone (CH 3COCH 3) followed by hydrolysis gives D (C 10H 180). Heating D with
with a deuterium atom on the methyl group C. Reaction
concentrated H 2SO 4 gives E
(C 10H 16), which decolorizes two equivalents of Br 2
to give F (C 10H 16Br 2). E
undergoes hydrogenation with excess H 2 and a Pt catalyst to give isobutylcyclohexane.
O The correct structure of C is
OH
O The correct structure of D is
O The correct structure of C is
Br
OI The correct structure of F is
8r
Isoprene has sometimes been used as a starting material in the laboratory synthesis of terpenes. In one such synthesis, the first step is the electrophilic addition of 2 mol of hydrogen bromide to isoprene to give 1,3-dibromo-3-methylbutane.Write a series of equations describing the mechanism of this reaction.
Chapter 16 Solutions
EBK ORGANIC CHEMISTRY
Ch. 16 - Prob. 16.1PCh. 16 - Prob. 16.2PCh. 16 - Prob. 16.3PCh. 16 - Prob. 16.4PCh. 16 - Prob. 16.5PCh. 16 - Prob. 16.6PCh. 16 - Prob. 16.7PCh. 16 - Prob. 16.8PCh. 16 - Prob. 16.9PCh. 16 - Prob. 16.10P
Ch. 16 - Prob. 16.11PCh. 16 - Prob. 16.12PCh. 16 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Prob. 16.16PCh. 16 - Prob. 16.17PCh. 16 - Prob. 16.18PCh. 16 - Prob. 16.19PCh. 16 - Prob. 16.20PCh. 16 - Prob. 16.21PCh. 16 - Prob. 16.22PCh. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Prob. 16.25PCh. 16 - Prob. 16.26PCh. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - Prob. 16.29PCh. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Prob. 16.32PCh. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Prob. 16.35APCh. 16 - Prob. 16.36APCh. 16 - Prob. 16.37APCh. 16 - Prob. 16.38APCh. 16 - Prob. 16.39APCh. 16 - Prob. 16.40APCh. 16 - Prob. 16.41APCh. 16 - Prob. 16.42APCh. 16 - Prob. 16.43APCh. 16 - Prob. 16.44APCh. 16 - Prob. 16.45APCh. 16 - Prob. 16.46APCh. 16 - Prob. 16.47APCh. 16 - Prob. 16.48APCh. 16 - Prob. 16.49APCh. 16 - Prob. 16.50APCh. 16 - Prob. 16.51APCh. 16 - Prob. 16.52APCh. 16 - Prob. 16.53APCh. 16 - Prob. 16.54APCh. 16 - Prob. 16.55APCh. 16 - Prob. 16.56APCh. 16 - Prob. 16.57APCh. 16 - Prob. 16.58APCh. 16 - Prob. 16.59APCh. 16 - Prob. 16.60APCh. 16 - Prob. 16.61APCh. 16 - Prob. 16.62APCh. 16 - Prob. 16.63APCh. 16 - Prob. 16.64APCh. 16 - Prob. 16.65APCh. 16 - Prob. 16.66APCh. 16 - Prob. 16.67APCh. 16 - Prob. 16.68AP
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