PROBLEMS 8.17 Write the structure of the principal organic product to be expected from the reaction of 1-bromopropane with each of the following: (a) Sodium iodide in acetone 0 (b) Sodium acetate (CH-CONa) in acetic acid (c) Sodium ethoxide in ethanol

PROBLEMS 8.17 Write the structure of the principal organic product to be expected from the reaction of 1-bromopropane with each of the following: (a) Sodium iodide in acetone 0 (b) Sodium acetate (CH-CONa) in acetic acid (c) Sodium ethoxide in ethanol

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 64AP: The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold...

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Question

For problem 8.17, all of the reactions will be SN2. For each reaction, identify and evaluate each nucleophile (strong? weak? Strong or weak as a base?) Also, evaluate each solvent as polar protic or polar aprotic. I recommend drawing the structure of each solvent.

PROBLEMS
8.17 Write the structure of the principal organic product to be expected from the reaction of
1-bromopropane with each of the following:
(a) Sodium iodide in acetone
0
(b) Sodium acetate (CH₂CONa) in acetic acid
(c) Sodium ethoxide in ethanol
(d) Sodium cyanide in dimethyl sulfoxide
(e) Sodium azide in aqueous ethanol
(f) Sodium hydrogen sulfide in ethanol
(g) Sodium methanethiolate (NaSCH,) in ethanol

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