Lecture No 7

Q. Compound A reacts faster by the SN2 mechanism than the compound B

H3C CH3 H3C CH3

Br

Br

A
Nu H H H3C H3C H Br H3C CH3 H

B
Nu

Br

less hindered approach

Q. Compound A reacts faster by the SN1 mechanism than compound B

Br Br

Epoxides

+ + X X

TS

Epoxides
H H Y O H H H Y O Y H H OH Y O H

OH

(Product formed)

Q.

But 1. Ph3P, X2 CH2Cl2 2. H2O O ~95%

But

OH

Whereas
But 1. Ph3P, X2 CH2Cl2 2. H2O O ~95% HO X But

X = Cl, Br, I

Bu

But X

But

But O

OH

But X

But X

Br C6H5 C6H5 CH3 OH

H3C

C6H5

(faster)

C6H5

Br C6H5 C6H5 CH3 OH

H3C

C6H5

(slower)

C6H5

H
Br

Br H3C Ph H OH Ph H Ph Ph

CH3 H H OH

faster

slower

Br C6H5 H H CO2H COC6H5 C5H5N C6H5 H CO2H COC6H5

C6H5

CO2H

COC6H5

Whereas
HO2C H

Br C6H5 COC6H5 H C5H5N C6H5 H

COC6H5

Br C6H5 H CO2H H COC6H5 C5H5N C6H5 H

COC6H5

Predict the product of following reaction

OMe

HO2C HO NH2

HNO2

Q.

CH3

CH3

CH3

NaOEt Cl

(faster reaction)

1:3 CH3 NaOEt Cl slower) CH3

(250 times

Me

OEt H
Me

Cl

Cl Cl Me

Cl

Me H OEt

(slower reaction)

Q.

Br
Br

(faster)
Br Br I

(slower)

Br

Br

fast
Br Br Br Br I Br I I

fast

I Br

fast

slow
I

Reactions of 2-bromo-4-phenylcyclohexanols with base and silver oxide

OH

OH or C6H5 Ag2O
Br O

C6H5

H C6H5 Br OH C6H5 Br C6H5 Br OH OH or Ag2O C6H5

OH or Ag2O

OH H OH C6H5 Br Ag2O C6H5 C6H5

CHO

Br OH C6H5 OH O

SN2 reactions (syn mode)

H OCOR/ H Bu
t

H N + N + H

R/CO2H

OCOR/ H But +

H N N +

R/CO2H

(R/ = Cl2C6H3-)

It is more difficult to form an acetal of compound A than of B. Why?

O O HO OH O

H+

A
O O HO OH O

H+