Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 8, Problem 50P
For each of the following
a. 3-bromo-2,2,3-trimethylpentane
b. 4-bromo-2,2,3,3-tetramethylpentane
c. 3-bromo-2,3-dimethylpentane
d. 3-bromo-3,4-dimethylhexane
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What are the correct IUPAC names for ALL possible monohalogenation substrate products that could form when the substrate 2-methylbutane undergoes monohalogenation with Cl2 in the presence of UV light.
a. 3-chloro-2-methylbutane
b. 1-chloro-2-methylbutane
c. 1,2-dichloro-2-methylbutane
d. 2-chloro-2-methylbutane
e. 4-chloro-2-methylbutane
f. 2-chloro-3-methylbutane
g.1-chloro-3-methylbutane
h. 1,2-dichloro-3-methylbutane
Draw all possible stereoisomers for each of the following. Indicate those compounds for which no stereoisomers are possible.
a. 1-bromo-2-chlorocyclohexane b. 2-bromo-4-methylpentane c. 1,2-dichlorocyclohexane d. 2-bromo-4-chloropentane e. 1-bromo-4-chlorocyclohexane f. 1,2-dimethylcyclopropane g. 4-bromo-2-pentene h. 3,3-dimethylpentane i. 1-bromo-2-chlorocyclobutane j. 1-bromo-3-chlorocyclobutane
• Question 7: What alkenes are formed from each alkyl halide by an E2 reaction?
Use the Zaitsev rule to predict the major product.
[The Zaitsev rule: The major product in ß elimination has the more substituted
double bond.]
CH3 H
1
a. CH3-C-C-CH₂CH3
1
H Br
1
b.
on 8: Draw the SN1
CH3
Br
CH3
C.
d.
CH3
CI
-CH3
CH3
El products formed in the reaction of (CH3)3CBr
Chapter 8 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 8.1 - Prob. 2PCh. 8.1 - Does increasing the energy barrier for an SN2...Ch. 8.1 - Arrange the following alkyl bromides in order from...Ch. 8.2 - Prob. 7PCh. 8.2 - Which reaction in each of the following pairs...Ch. 8.2 - Prob. 9PCh. 8.2 - Prob. 11PCh. 8.3 - Draw the substitution products that will be formed...Ch. 8.4 - Arrange the following alkyl halides in order from...Ch. 8.5 - Prob. 14P
Ch. 8.5 - Which of the following reactions will go faster if...Ch. 8.6 - After a proton is removed from the OH group, which...Ch. 8.6 - Draw the product of each of the following...Ch. 8.9 - Prob. 20PCh. 8.9 - Prob. 21PCh. 8.11 - Why do the SN1/E1 reactions of tertiary alkyl...Ch. 8.11 - Prob. 23PCh. 8.11 - Prob. 24PCh. 8.12 - Prob. 25PCh. 8.12 - Prob. 26PCh. 8.12 - Prob. 27PCh. 8.12 - a In which solvent would tert-butyl bromide...Ch. 8.13 - What would be the best way to prepare the...Ch. 8 - Methoxychlor is an insecticide that was intended...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Explain how the following changes would affect the...Ch. 8 - Prob. 38PCh. 8 - Draw the major product obtained when each of the...Ch. 8 - Which alkyl halide in Problem 39 can undergo an El...Ch. 8 - Prob. 42PCh. 8 - Prob. 43PCh. 8 - Prob. 44PCh. 8 - Prob. 45PCh. 8 - Starting with bromocyclohexane, how could the...Ch. 8 - Prob. 48PCh. 8 - Fill in the blanks in the following chemical...Ch. 8 - For each of the following alkyl halides, indicate...Ch. 8 - Prob. 51PCh. 8 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 8 - An ether can be prepared by an SN2 reaction of an...Ch. 8 - Give two sets of reactants (each set including an...Ch. 8 - Show how the following compounds could be...Ch. 8 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Draw the structures of the products obtained from...Ch. 8 - cis-4-Bromocyclohexanol and...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - In which solventethanol or diethyl etherwould the...Ch. 8 - The pKa of acetic acid in water is 4.76. What...
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