Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 6, Problem 1LGP

Consider the solvolysis reaction of (1S, 2R)-1-bromo-1,2-dimethylcyclohexane in 80% 80 % H 2 O / 20 % C H 3 C H 2 O H at room temperature.

(a) Write the structure of all chemically reasonable products from this reaction and predict which would be the major one.

(b) Write a detailed mechanism for formation of the major produce.

(c) Write the structure of all transition stares involved in formation of the major produce.

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(a) (i) 3-Methyl-2-butanol will react with sulphuric acid to give two isomeric alkenes in 3:1 proportions.(i) Write down the structures for these alkenes and assign appropriate systematic names to them.                                                                                                                                             (ii) Name the most abundant isomer.                                                                            (iii) Write down detailed mechanism for the formation of a minor product.
Give to all parts?   (a) Give the complete mechanism for the reaction of trans-2-butene with Br2 in excess H2O. (b) Name the products (including stereochemistry). (c) Give the complete mechanism for the reaction of trans-2-butene with Br2 in excess H2O. (d) Name the products (including stereochemistry).
1. Outline mechanisms for the following addition reactions. (a) (b) ICI (c) HBr HI 2. Provide mechanistic explanations for the following observations (a) HCI CI (b) HCI 3. Treatment of 3-methylcyclohexene with HCl yields two products, 1-chloro-3- methylcyclohexane and 1-chloro-1-methylcyclohexane. Draw a mechanism to explain this result. 4. Addition of HBr to which of the following alkenes will lead to a rearrangement? a. CH;=C(CH,)CH,CH, b. CH3CH=CHCH,CH; c. CH3CH=CHCH(CH,),
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