Organic Chemistry I: Studying Sn1 Reactions (nucleophilic substitution at satura

ID: 904835 • Letter: O

Question

Organic Chemistry I: Studying Sn1 Reactions (nucleophilic substitution at saturated carbon)

Purpose of the experiment: Investigate some factors that influence the rate of Sn1 reactions.

Part one: Effect of the leaving group

Reaction: 2-bromo-2-methylpropane +50% 2- propanol----Time (seconds): 17

2-chloro-2-methylpropane +50% 2-propanol------Time (seconds): 4 mins: 30 s

Question:

1) When you compare both reactions above what were the relative rates of the two reactions?

2) Based on the relative rates for the reactions shown above, which is the better elaving group, Br^- or Cl^- ?

HBr is stronger acid than HCl. Are these results consistent with the relative base strengths of these two ions? Please, explain your answer.

1.
1ST reaction takes 17 s
2nd reaction took 4 min 30 s
So reaction 1 is faster
Lesser the time taken, faster is the reaction rate

rate of 1 / rate of 2 = 4 min 30 s / 17 s = 270 s/17 s= 15.88

rate of 1 = 15.88 times rate of 2

2.
Br- is better leaving group
Since 1st reaction is faster, Br- left easily and hence it is better leaving group

3.
HBr is stronger acid, So Br- must be weaker base. But Br- is reacting easily with propanol which acts as acid here. So reslut is not consistent

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