Question

Select the best conditions for the reactions.

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Answer #1
Concepts and reason

In general, primary alkyl halides undergo SN2{\rm{S}}{{\rm{N}}_{\rm{2}}} reactions with strong nucleophiles and tertiary alkyl halides undergo SN1{\rm{S}}{{\rm{N}}_1} reaction with weak nucleophiles.

Fundamentals

Strong nucleophile is required for SN2{\rm{S}}{{\rm{N}}_{\rm{2}}} reaction and these reactions are occurred in polar aprotic solvents (i.e. DMSO, DMF etc.).

Weak nucleophile is required for SN1{\rm{S}}{{\rm{N}}_1} reaction. If a nucleophile is strong then there is a chance for the E2 product formation.

Part a

The reaction is,

CH3
CH3
NaOCH3, DMSO
CH3
Br
H3C
НЫС
1-bromo-3-methylbutane
1-methoxy-3-methylbutane

Part b

The reaction is,

CH3
- CH3
ÇHz
|
Br
CH3OH
CH3
H₂C
H3C
2-bromo-2-methylbutane
2-methoxy-2-methylbutane

Ans: Part a

Thus, the choice of reagent is NaOCH3,DMSO{\rm{NaOC}}{{\rm{H}}_{\rm{3}}}{\rm{,}}\;{\rm{DMSO}} .

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