Вы находитесь на странице: 1из 5

YOUR STUDENT NUMBER:

Year 2 Seminars, 06524, Semester 2, 2007


Bifunctional and Heterocyclic Chemistry Test
1.

Answer all parts


(a)

For each of the following pairs of molecules, predict and explain which is the more
basic.

(i)
N
H

P
H

H+
N

N
H

more basic

less acidic

H+
P
H
less basic
more stable due to less
repulsions associated
with the P lone pair

P
H

more acidic

YOUR STUDENT NUMBER:

(ii)

Se
Se

H+
Se

Se

more basic
less stable due to the
lone pair being near
sp3 hybridised

Se

less acidic

H+

Se
H

less basic
more stable due to the
lone pair being near
sp2 hybridised

(b)

more acidic

Which of the following molecules are aromatic, anti-aromatic or simply conjugated?

N
S
PCl4

N
H

YOUR STUDENT NUMBER:

N
S
PCl4

N
H

Cyclic

yes

yes

yes

Planar

yes

yes

yes

yes

yes

yes

Anti-aromatic

Aromatic

Aromatic

Continuous
conjugation
Number of
contributing
electrons

YOUR STUDENT NUMBER:

2.

(a)

Mark the acidic -hydrogen atoms on the following structures.


CH3CH2COCH2CH2CH2COOCH3

CH3COCH2COOCH3

H3C

O
O

H
O

CH3COCH2CH2CH2CN

(b)

H
H
H

O
H
H

CH3

Work out the structures of all the products that may be formed when a mixture of
compounds A and B are reacted in the presence of a slight molar excess of sodium
ethoxide.
PhCH2COOC2H5

PhCH2CH2COOC2H5

Four possible products may be formed


Self-condensation of A

O
Ph

C
H

O
Ph

OEt

Ph
C

OEt

C
C
O

O
Ph

OEt
Ph

EtOH

Ph

Self-condensation of B

Ph

C
H

O
OEt

Ph
Ph

OEt

Ph

aq. HCl
work up

OEt

Ph

Ph

Ph

OEt

O
Ph

OEt

EtO
O

Ph

EtO-H

OEt
OEt

O
OEt

Enolate of A plus ester B

OEt

Ph
Ph

Enolate of B plus ester A

YOUR STUDENT NUMBER:

3.

Complete the following reaction scheme providing brief mechanistic detail.


Et

Et
O

HCl

C (C8H12O)

For a detailed mechanism see your lecture notes on page 50.

Вам также может понравиться