Organic Chemistry
7th Edition
ISBN: 9780321803078
Author: Bruice, Paula Yurkanis
Publisher: Pearson College Div
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Question
Chapter 13, Problem 40P
Interpretation Introduction
Interpretation:
The value for the relative east of removing a hydrogen atom from tertiary, secondary and primary hydrogen carbons by a chlorine radical has to be given.
Concept introduction:
Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.
Chlorine radical forms a tertiary radical five times faster than a primary radical and it forms a secondary radical 3.8 times faster than a primary radical.
Relative rates of alkyl radical formation by a chlorine radical at 125 °C.
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A chemist wanted to determine experimentally the relative ease of removing a hydrogen atom from a tertiary, a secondary, and a primary carbon by a chlorine radical. He allowed 2-methylbutane to undergo chlorination at 300 °C and obtained as products 36% 1-chloro-2-methylbutane, 18% 2-chloro-2-methylbutane, 28% 2-chloro-3-methylbutane, and 18% 1-chloro-3-methylbutane. What values did he obtain for the relative ease of removing a hydrogen atom from tertiary, secondary, and primary hydrogen carbons by a chlorine radical under the conditions of his experiment?
When 2-methylpropane is monochlorinated in the presence of light at room temperature, 36% of the product is 2-chloro-2-methylpropane and 64% is 1-chloro-2-methylpropane. From these data, calculate how much easier it is to remove a hydrogen atom from a tertiary carbon than from a primary carbon under these conditions.
5. Acetone and 2-propanol are chemically interconvertible. Reduction (by the addition of the equivalent of H2) of acetone yields 2-propanol. Conversely, oxidation (by the removal of the equivalent of H2) of 2-propanol yields acetone.
Is the evaporation data for these substances the same or different? If different, can you account for why this may be the case from a comparison of the Lewis structures of each substance and the IMFs present in each substance? Explain.
Chapter 13 Solutions
Organic Chemistry
Ch. 13.2 - Prob. 1PCh. 13.2 - Write the steps for formation of...Ch. 13.3 - Prob. 3PCh. 13.4 - Prob. 4PCh. 13.5 - Prob. 7PCh. 13.5 - a. Would chlorination or bromination produce a...Ch. 13.5 - Prob. 10PCh. 13.6 - Prob. 11PCh. 13.7 - Prob. 12PCh. 13.7 - Prob. 13P
Ch. 13.8 - Prob. 14PCh. 13.8 - Draw the stereoisomers of the major...Ch. 13.9 - a. How many stereoisomers are formed from the...Ch. 13.9 - Prob. 17PCh. 13.9 - Prob. 19PCh. 13.9 - Prob. 20PCh. 13.9 - Prob. 21PCh. 13.10 - Prob. 22PCh. 13.11 - How many atoms share the unpaired electrons in...Ch. 13.11 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - Prob. 26PCh. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - Prob. 31PCh. 13 - Prob. 32PCh. 13 - Prob. 33PCh. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Starting with cyclohexane, how could the following...Ch. 13 - a. Propose a mechanism for the following reaction:...Ch. 13 - What stereoisomers are obtained from the following...Ch. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Draw the products of the following reactions,...Ch. 13 - a. What five-carbon alkene forms the same product...Ch. 13 - Prob. 44PCh. 13 - Prob. 45PCh. 13 - Prob. 46PCh. 13 - Explain why the rate of bromination of methane...Ch. 13 - Prob. 48P
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