ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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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.
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,),
(a) Account for the following :(i) Electrophilic substitution reactions in haloarenes occur slowly.(ii) Haloalkanes, though polar, are insoluble in water.(b) Arrange the following compounds in increasing order of reactivity towards SN2 displacement:2-Bromo-2-Methylbutane, 1-Bromopentane, 2-Bromopentane
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