Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 10, Problem 23P
Interpretation Introduction
Interpretation:
The number of different isomers expected from the chlorination of (R)-2-chlorobutane and the number of fractions obtained by fractional distillation are to be given. Also, the optical activity of these fractions is to be checked.
Concept introduction:
A mixture of isomeric monochlorinated products is formed by the chlorination of higher
The optically active compounds are those that contain at least one chiral center.
A chiral center is a carbon atom attached to 4 different substituents.
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Give reasons:
(a) n-Butyl bromide has higher boiling point than f-butyl bromide.
(b) Racemic mixture is optically inactive.
(c) The presence of nitro group (-N02) at o/p positions increases the reactivity of haloarenes towards nucleophilic substitution reactions
2. (a) Reaction of an alkene with ozone followed by an
oxidative workup gives the product shown. What is the
structure of alkene A?
A
(b) Compounds B and C both have the
formula C10H16. Hydrogenation of either
compound over Pt gives the same product,
cis-1-isopropyl-4-methylcyclohexane.
Ozonolysis with reductive workup
fragments the two compounds differently,
as shown below. What are the structures of C
B and C? (CHCl3, chloroform, is the
solvent.)
B
1) 03, CHCI 3
2) (CH3)2S
1) 03, CHC13
2) (CH3)2S
H
O
1) 03
2) H₂O2, H₂O
H3C-
H
O
CH3
3. (a) Draw the structures of all enols that would spontaneously form this ketone,
including stereoisomers.
+
+
I
HO₂C
H
+
La
CH3CH₂-C-CH(CH3)2
O=
(b) Would alkyne hydration be a good preparative method for this compound? If so, give the reaction. If not,
explain why.
11:43
Q1.
(a)
(c)
(d)
(b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with
ethanolic potassium hydroxide.
(i) Explain what is meant by the term stereoisomers.
Library
Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with
ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH3)2C=CH₂
Name of mechanism
Mechanism
(ii)
Draw the structures and give the names of the two stereoisomers of
but-2-ene.
Stereoisomer 1
Name
(iii) Name this type of stereoisomerism.
Select
Name
Stereoisomer 2
When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide,
2-methylpropan-2-ol is formed as shown by the following equation.
CH3
H₂C-C-CH3 + KOH
Br
Page 2 of 14
CH3
H3C-C-CH3 + KBr
ОН
State the role of the hydroxide ions in this reaction.
Write an equation for the reaction that occurs when CH3CH₂CH₂CH₂Br reacts with
an excess of ammonia. Name the organic product of this reaction.
Equation
Name of product
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Chapter 10 Solutions
Organic Chemistry
Ch. 10 - Prob. 1PPCh. 10 - Prob. 2PPCh. 10 - Practice Problem 10.3 How would the molecular ion...Ch. 10 - Prob. 4PPCh. 10 - Prob. 5PPCh. 10 - Prob. 6PPCh. 10 - Practice Problem 10.7 Chlorination reactions of...Ch. 10 - Prob. 8PPCh. 10 - Prob. 9PPCh. 10 - Prob. 10PP
Ch. 10 - Prob. 11PPCh. 10 - Practice Problem 10.12 Benzylic radicals, due to...Ch. 10 - Prob. 13PPCh. 10 - Practice Problem 10.14 Show how the following...Ch. 10 - Prob. 15PPCh. 10 - Prob. 16PPCh. 10 - Prob. 17PPCh. 10 - Prob. 18PCh. 10 - Explain the relative distribution of produces...Ch. 10 - 10.20 Which of the following compounds can be...Ch. 10 - Prob. 21PCh. 10 - Prob. 22PCh. 10 - Prob. 23PCh. 10 - Prob. 24PCh. 10 - 10.25 List in order of decreasing stability all of...Ch. 10 - Prob. 26PCh. 10 - Prob. 27PCh. 10 - Prob. 28PCh. 10 - Starting with the compound or compounds indicated...Ch. 10 - Prob. 30PCh. 10 - 10.31 Synthesize each of the following compounds...Ch. 10 - Synthesize each of die following compounds by...Ch. 10 - Prob. 33PCh. 10 - Prob. 34PCh. 10 - Prob. 36PCh. 10 - The halogen atom of an alkyl halide can be...Ch. 10 - Prob. 38PCh. 10 - Prob. 39PCh. 10 - Write a mechanism for the following reaction.Ch. 10 - 10.41 Hydrogen peroxide and ferrous sulfate react...Ch. 10 - Prob. 42PCh. 10 - If one were to try to draw the simplest Lewis...Ch. 10 - Prob. 1LGPCh. 10 - 2. (a) Propose a synthesis of 2-methoxypropene...
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