2019s/w-NMR

2019S-41-Q8
After we deduce the structure of X, we will do this question.
 triplet
quartet

4 types of H.
X contains CH3CH2- group.
According to the molecular formula, it may be a carboxylic acid or an ester.

No peak at chemical shift 9.0-13.0, so X is not a carboxylic acid.

 singlet
singlet

triplet

quartet
So X is not an ester.
(CO ) CH2O (CH3 ) CH2O
singlet
singlet CH3
CH3
CO
CH3 CO

(CH3 ) CH2O triplet (CO ) CH2O

quartet
√
√

√
Chemical shift ＞ 3.5
Iodoform reaction occurs, so X contains CH3 CO- group.
 After we deduce the structure of X, we do this question.

. Free radical can’t be detected.

H atoms are in two different
chemical environments.

W contains three CH3 groups.

*
2019W-41-Q9

Base: a proton acceptor.

Ester: neutral compound.

H+

Phenylamine: Basic
Butamben is a weaker base than ammonia. Because the lone-pair on N
atom is delocalized in the benzene ring. This decreases the electron
density of the lone-pair on N atom and makes lone-pair on N atom less
available to accept proton.
-NH2: electron- Phenylamine
donating group,
diazotisation
2,4,6-directing
Electrophilic
substitution
Alkaline hydrolysis of ester
 Adjacent C atom has 2 H atoms attached.

2
Adjacent C atom has 2 H atoms attached.
Labile proton
2019w-42-Q8

Free radical Nucleophilic

substitution substitution

Nitrile
Pure KCN in ethanol, reflux
bromine,
2 C atoms
sunlight
1,2-dibromoethane

4 C atoms: extend the carbon chain

1,1-dibromoethane
Three peaks of proton
 CH3
COO
H
CHCO-
2
3
2019w42-Q9

One electron from N atom in the

benzene ring

5 C atoms in the ring, so 5 electrons.

2 electrons

2 electrons

1+5+2+2=10
120°
PCl5, or SOCl2 Condensation reaction
or addition- elimination
reaction

Acyl chloride Ammonia, Room

temperature
 Amide is neutral.

Alkaline hydrolysis
Acidic hydrolysis of
of amide
amide
 Reduction

amine
amide
 CH2

Amide is neutral. The lone-pair

Alkyl group: an electron-donation
on N atom is delocalized into
group ， so it can increase the electron
the C=O group. In amide, there
density on N atom in NH2 group.
is a delocalized Π system.
No. of carbon atoms in nicotinamide is 6.