Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Question
Chapter 10.9, Problem 21P
Interpretation Introduction
Interpretation:
Variation of substitution to elimination product when reaction of propyl bromide ion with
Concept Introduction:
Strong base favours elimination product, and a bulky base favours elimination product.
A high temperature favors elimination product. Steric hindrance favors elimination product.
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CH3
CH3
Br-
Br2
CH2CI2
CH3
CH3
H3C
H3C
Br
Electrophilic addition of bromine, Br2, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a
bromonium ion. The reaction occurs in an anhydrous solvent such as CH2C12.
In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to
steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry
is formed.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
CH3
CH3
Br-
.CH3
.CH3
H3C
H3C
:Br
:Br:
Br
Brz
CH3
CH3
H3C
CH2CI2
H3C
Br
Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion.
The reaction occurs in an anhydrous solvent such as CH,Cl).
In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes,
the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
Br:
:Br:
.CH3
H3C
H3C
CH3
Br:
If the following molecules undergo free radical substitution, what is the order in which the hydrogen is easily replaced by bromine?
Chapter 10 Solutions
Organic Chemistry
Ch. 10.2 - Prob. 1PCh. 10.2 - Prob. 2PCh. 10.2 - Prob. 3PCh. 10.2 - Prob. 4PCh. 10.3 - Four alkenes are formed from the E1 reaction of...Ch. 10.3 - If 2-fluoropentane could undergo an E1 reaction,...Ch. 10.3 - Prob. 7PCh. 10.3 - Propose a mechanism for the following reaction:Ch. 10.4 - Prob. 9PCh. 10.4 - What products will be obtained from the El...
Ch. 10.4 - Prob. 11PCh. 10.5 - Prob. 12PCh. 10.6 - Prob. 14PCh. 10.7 - Why do cis-1-bromo-2-ethylcyclohexane and...Ch. 10.7 - Which isomer reacts more rapidly in an E2...Ch. 10.7 - Prob. 18PCh. 10.8 - Prob. 19PCh. 10.8 - Prob. 20PCh. 10.9 - Prob. 21PCh. 10.9 - Explain why only a substitution product and no...Ch. 10.9 - Prob. 23PCh. 10.9 - Prob. 24PCh. 10.9 - Prob. 25PCh. 10.9 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 10.10 - A small amount of another organic product is...Ch. 10.10 - What is the best way to prepare the following...Ch. 10.10 - Prob. 29PCh. 10.10 - Prob. 30PCh. 10.10 - Why is a cumulated diene not formed in the...Ch. 10.10 - What product is obtained when the following...Ch. 10.11 - Prob. 33PCh. 10.11 - Prob. 34PCh. 10 - Draw the major product obtained when each of the...Ch. 10 - Prob. 36PCh. 10 - a. Indicate how each of the following factors...Ch. 10 - Prob. 38PCh. 10 - A chemist wanted to synthesize the...Ch. 10 - Prob. 40PCh. 10 - Prob. 41PCh. 10 - Prob. 42PCh. 10 - Starting with an alkyl halide, how could the...Ch. 10 - Indicate which species in each pair gives a higher...Ch. 10 - Prob. 45PCh. 10 - For each of the following alkyl halides, indicate...Ch. 10 - Prob. 47PCh. 10 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 10 - Prob. 49PCh. 10 - When the following compound undergoes solvolysis...Ch. 10 - cis-1-Bromo-4-tert-butylcyclohexane and...Ch. 10 - Draw the substitution and elimination products.Ch. 10 - Prob. 53PCh. 10 - Prob. 54PCh. 10 - Which of the following hexachlorocyclohexanes is...Ch. 10 - Explain why the rate of the reaction of...Ch. 10 - Prob. 57PCh. 10 - Two elimination products are obtained from the...Ch. 10 - Draw the structures or the product of the obtained...Ch. 10 - How could you prepare the following compounds from...Ch. 10 - cis-4-Bromocyclohexanol and...Ch. 10 - Prob. 62PCh. 10 - Prob. 63P
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