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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
(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
N
S
PCl4
N
H
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
2.
(a)
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
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
OEt
Ph
Ph
3.
Et
O
HCl
C (C8H12O)