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 19P
Explain the relative distribution of produces below using reaction energy diagrams for the hydrogen abstraction step that leads to each product. (The rare-determining seep in radical halogenation is the hydrogen abstraction step.) In energy diagrams for the two pathways, show die relative energies of the transition scares and of the alkyl radical intermediate char results in each case.
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The high reactivity of alkyl halides can be explained in terms of nature of C-X bond which is highly polarized
covalent bond due to large difference in the electronegativities of carbon and halogen atom. This polarity
is responsible for the nucleophilic substitution reactions of alkyl halides which mostly occur by Swa and Swa
mechanisms. Sy reaction is a two-step process and in the first step, R-X ionizes to give carbocation (slow
process). In the second step, the nucleophile attacks the carbocation from either side to form the product
(fast process). In Swi reaction, there can be racemization and inversion. Swi reaction is favored by heavy
(bulky) groups on the carbon atom attached to halogens. i.e., R,C-X>R;CH-X>R-CH,X>CH,X. In Sna reaction,
the strong nucleophile OH attacks from the opposite side of the chlorine atom to give an intermediate
(transition state) which breaks to yield the product (alcohol) and leaving (X) group. The alcohol has a
configuration opposite to that of the…
Heterocyclic compounds plays an important role in our daily life. They are mainly used in
pharmaceutical and agrochemical products to name a few.
3. It is required to introduce a halogen group to a five membered ring, thiophene. Discuss
the reaction mechanism involved in the reaction by selecting a suitable halogen group and
analyze why a particular substituted product obtained after the reaction is predominant
over the other possible product(s) with the help of reactions.
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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