Competing Nucleophiles

Question 1

General idea?

Answer 1

“What’s the better nucleophile on substrate?”

Question 2

Part A/part B?

Answer 2

Running reactions

Question 3

Part C?

Answer 3

Analysis

Question 4

What’s the nucleophile (halogen) mixture for?

Answer 4

See which is a better nucleophile

Question 5

If reaction is pure SN2, what should ratio of RCl to RBr be?

Answer 5

&laquo_space;1, because nucleophile matters in the rate law

Question 6

If reaction is pure SN1, what should ratio of RCl to RBr be?

Answer 6

1:1, because carbocation formation is all that matters rate-wise

Question 7

What are you comparing at the end?

Answer 7

Percent of each nucleophile

Question 8

Changes?

Answer 8

Start part A first

While reaction is refluxing, do part B

Be quick when performing part B extraction

When finished with part B, go back to A

Question 9

How does reaction schemes work? (know for final)

Answer 9

Start at bottom left

Make arrows showing each extraction (e.g. organic/aqueous)

Make more arrows showing new reaction as you get closer to purified compound

Question 10

Post lab question: How come you see 3-chloro/3-bromopentane?

Answer 10

alkene intermediate