i need an explenation for these result? why some of the reactions slow and why a

Question

i need an explenation for these result? why some of the reactions slow and why are some fast? it is for a lab report.

thank you

AgNO3       SN1

NaI                    SN2

2-bromobutane

Slow to react (with heat)

Fast reaction

2-bromo-2-methylpropane

Medium speed

Slow to react ( heat)

1-bromobutane

Fast reaction

Slow to react

Bromocyclohexane

Fast reaction

Slow to react ( heat)

Bromotoluene

Fast reaction

Fast reaction

Bromobenzene

No reaction

Slow reaction (heat)

AgNO3       SN1

NaI                    SN2

2-bromobutane

Slow to react (with heat)

Fast reaction

2-bromo-2-methylpropane

Medium speed

Slow to react ( heat)

1-bromobutane

Fast reaction

Slow to react

Bromocyclohexane

Fast reaction

Slow to react ( heat)

Bromotoluene

Fast reaction

Fast reaction

Bromobenzene

No reaction

Slow reaction (heat)

Explanation / Answer

1. nucleofugality or leaving character of I- is higher that is why reaction with NaI is fast.

2. 2-bromo-2-methylpropane is tertiary substrate so it will give SN1 moderate rate but SN2 slow becoz od steric hindrance

3. same as 1

4. 2ndray carbocation in this case both reaction should occur at equal rate but due to the bulk nature of I , SN2 does not favour

5/

6. carbocation is not stable so SN1 does not occur, SN2 occur slowly due to steric hindrance

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