Year 2 Seminars, 06524, Semester 2, 2005: Bifunctional Chemistry Test

WRITE YOUR ANSWERS ON THIS SHEET

Q1

Label all of the acidic hydrogen atoms on the molecules shown.

O

H
H
H

Q2

Ph H
N
H
H
H

O
O

(3 marks)

H
H

H
H

Draw a tautomeric structure for each of the above

OH

OH
O

(2 marks each)

O
O

or

OH

or

(all possible, but first is most stable)

OH
N
H

Q3

Ph or

OH

OH
N

Ph

Consider the scheme below then answer the questions:

OC2H5

Ph

NaOEt
O

O
C2 H5 O

(i)
(ii)
(ii)
(iv)

NaH
CH3I

NaOH (aq)

OC2H5

Work out structures for A, B and C.

Show the mechanism for the formation of A.
Show the mechanism for the formation of C.
What by-product is formed in producing C?
PTO

O
H3 C
Ph

ONa
ONa

HCl (aq)
heat

(2 marks each)
(4 marks)
(4 marks)
(1 mark)

O
H
Ph

OEt
OEt

H3C
Ph

O
A

OEt
OEt

OH
by-product is CO2

H3 C
Ph

O
C2H5O

OC2H5

O
OC2H5

C2H5O

H
H H
OC2H5
OC2H5
Ph
NaOEt Ph
O
O

Ph

- NaOEt

O
H
Ph

OC2H5
O

OC2H5
OC2H5
O

NaOEt

O
H
Ph

OC2H5

work up

OC2H5

OC2H5
OC2H5

Ph

O
B

aq. NaOH r.t.

Me
Ph

ONa
ONa

HCl (aq)
heat

OH

Me
Ph

O
C

O
Me
Ph

OH
OH
O

tautomerism

HO

Me
Ph

H
O

OH
Me

OH
Ph

O
C
O