EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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Chapter 13, Problem 70IP
Interpretation Introduction
Interpretation: The reason for the formation of the following major product needs to be explained.
Concept Introduction: Grignard reagent can act as a strong base as well as a strong nucleophile. The nature of the reaction depends on the reactant that is if the possibility of an attack of nucleophile or elimination is more.
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Butanone undergoes a nucleophilic addition with a Grignard reagent made from 1-bromopropane and magnesium metal in THF solution. The alkoxide formed from the nucleophilic addition is then conveted into the final product by the careful addition of dilute acid.
Complete the mechanism by following the instructions provided for each step.
Step 1. Nucleophilic Addition in THF
Write the mechanisms for the following reactions bellow, justifying each substitution position.
A chemist needs an ether to use as a solvent for a reaction and wants to synthesize it in one step from two of the following available reagents: sodium ethoxide, bromomethane, potassium tert-butoxide, and 2-bromo-2-methylpropane.
i) Which combination(s) will give a good yield of an ether? Illustrate, showing the mechanism of the reaction.
ii) Illustrate with a mechanism the reaction of one of the combinations that will not yield an ether?
Chapter 13 Solutions
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
Ch. 13.2 - Prob. 1LTSCh. 13.2 - Prob. 1PTSCh. 13.2 - Prob. 2PTSCh. 13.2 - Prob. 3ATSCh. 13.4 - Prob. 4CCCh. 13.5 - Prob. 2LTSCh. 13.5 - Prob. 5PTSCh. 13.5 - Prob. 6ATSCh. 13.5 - Prob. 7CCCh. 13.5 - Prob. 8CC
Ch. 13.5 - Prob. 9CCCh. 13.6 - Prob. 10CCCh. 13.7 - Prob. 11CCCh. 13.7 - Prob. 12CCCh. 13.8 - Prob. 3LTSCh. 13.8 - Prob. 13PTSCh. 13.8 - Prob. 14ATSCh. 13.9 - Prob. 15CCCh. 13.10 - Prob. 4LTSCh. 13.10 - Prob. 17ATSCh. 13.10 - Prob. 5LTSCh. 13.10 - Prob. 19ATSCh. 13.11 - Prob. 20CCCh. 13.12 - Prob. 6LTSCh. 13.12 - Prob. 7LTSCh. 13 - Prob. 26PPCh. 13 - Prob. 27PPCh. 13 - Prob. 28PPCh. 13 - Prob. 29PPCh. 13 - Prob. 30PPCh. 13 - Prob. 31PPCh. 13 - Prob. 32PPCh. 13 - Prob. 33PPCh. 13 - Prob. 34PPCh. 13 - Prob. 35PPCh. 13 - Prob. 36PPCh. 13 - Prob. 37PPCh. 13 - Prob. 38PPCh. 13 - Prob. 39PPCh. 13 - Prob. 40PPCh. 13 - Prob. 41PPCh. 13 - Prob. 42PPCh. 13 - Prob. 43PPCh. 13 - Prob. 44PPCh. 13 - Prob. 45PPCh. 13 - Prob. 46ASPCh. 13 - Prob. 47ASPCh. 13 - Prob. 48ASPCh. 13 - Prob. 49ASPCh. 13 - Prob. 50ASPCh. 13 - Prob. 51ASPCh. 13 - Prob. 52ASPCh. 13 - Prob. 53ASPCh. 13 - Prob. 54IPCh. 13 - Prob. 59IPCh. 13 - Prob. 60IPCh. 13 - Prob. 61IPCh. 13 - Prob. 62IPCh. 13 - Prob. 63IPCh. 13 - Prob. 64IPCh. 13 - Prob. 65IPCh. 13 - Prob. 66IPCh. 13 - Prob. 69IPCh. 13 - Prob. 70IPCh. 13 - Prob. 71IPCh. 13 - Prob. 72IPCh. 13 - Prob. 73IPCh. 13 - Prob. 74IPCh. 13 - Prob. 77CPCh. 13 - Prob. 79CPCh. 13 - Prob. 80CP
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