Decide on the mechanism for each substitution, and then pick the solvent that affords the faster reaction. a.(CH3CH2)2CClCH3 + CH3OH in CH3OH or DMSO b.CH3CH2CH2Br + −OH in H2O or c. DMF (CH3CH2)2CHCl + CH3O− in CH3OH or HMPA

Decide on the mechanism for each substitution, and then pick the solvent that affords the faster reaction. a.(CH3CH2)2CClCH3 + CH3OH in CH3OH or DMSO b.CH3CH2CH2Br + −OH in H2O or c. DMF (CH3CH2)2CHCl + CH3O− in CH3OH or HMPA

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 3CTQ

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

Decide on the mechanism for each substitution, and then pick the solvent that affords the faster reaction.

a.(CH₃CH₂)₂CClCH₃ + CH₃OH in CH₃OH or DMSO

b.CH₃CH₂CH₂Br + ⁻OH in H₂O or

c. DMF (CH₃CH₂)₂CHCl + CH₃O⁻ in CH₃OH or HMPA

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