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A Compilation of Structure Elucidation Questions

Chuah Wei Bin


1. (N2002/P3/Q8(either))
This question is about compound F, C
8
H
8
O
2
, which is formed when phenyl ethanoate, CH
3
CO
2
C
6
H
5
,
is warmed with aluminium chloride.
Compound F is insoluble in water, but dissolves in NaOH
(aq)
.
It reacts with 2,4-dinitrophenylhydrazine, 2,4-DNPH, but not with Fehlings solution.
With bromine water, F gives G, C
8
H
6
O
2
Br
2
.
With alkaline aqueous iodine followed by acidication, F gives H, C
7
H
6
O
3
.
Compound H dissolves in both NaOH
(aq)
and Na
2
CO
3(aq)
. Compound H can also be obtained by
reacting oil of wintergreen, J, with hot NaOH
(aq)
, followed by H
2
SO
4(aq)
.
CO
2
CH
3
OH
J
Deduce the structures of compounds F, G and H. Explain the chemistry of the reactions described,
writing equations where appropriate. [There is no need to comment on the chemistry of the formation
of F from phenyl ethanoate.]
2. (N2002/P3/8(or))
This question is about compound K, C
6
H
7
ON, which is formed when phenylhydroxylamine, C
6
H
5
NHOH,
is warmed with dilute sulfuric acid.
Compound K is not very soluble in water, but dissolves in HCl
(aq)
.
It also dissolves in NaOH
(aq)
, but not in Na
2
CO
3(aq)
.
On reaction with 1 mol of ethanoyl chloride, CH
3
COCl, K forms compound L, C
8
H
9
O
2
N.
L is no longer soluble in HCl
(aq)
, but is still soluble in NaOH
(aq)
. On reaction with Br
2(aq)
, L produces
compound M, C
8
H
7
O
2
NBr
2
. When Kis reacted with 2 mol of ethanoyl chloride, it produces compound
N, which is not soluble in either HCl
(aq)
or NaOH
(aq)
.
Compound K can be synthesised by treating phenol with dilute nitric acid, followed by reaction with
zinc metal and hydrochloric acid.
Deduce the structures of compounds K, L, Mand N. Explain the chemistry of the reactions described,
writing equations where appropriate. [There is no need to comment on the chemistry of the formation
of K from phenylhydroxylamine.]
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3. (CJC2011/P3/Q4(c))
A hydrocarbon A has the molecular formula of C
10
H
14
. When A is treated with hot aqueous acidied
KMnO
4(aq)
, benzoic acid is formed. When reacted with bromine in the presence of ultraviolet light,
A produced four isomeric monobromo compounds with the formula C
10
H
13
Br. Upon heating with
alcoholic NaOH, two of the monobromo compounds B and C gave the same compound which can exist
as a pair of geometric isomers, D and E. Heating B with aqueous NaOH produces compound F which
does not react with acidied potassium dichromate(VI). Suggest the structures of A to F, explaining
your reasoning.
4. (TPJC2011/P3/Q5(c))
Compound M (C
10
H
13
O
3
N) reacts fully with Br
2(aq)
in the ratio 1 : 2, but it does not decolourise
cold alkaline KMnO
4
. M also shows no reaction with PCl
5
. When warmed in aqueous alkali and
subsequently neutralised, Mproduces P (C
8
H
11
O
2
N) and Q (C
2
H
4
O
2
). P changes acidied K
2
Cr
2
O
7
from orange to green, and forms R (C
8
H
9
O
3
N) in the process. Both Q and R react with Na
2
CO
3
solution to give eervescence. R also reacts fully with Br
2(aq)
in the ratio 1 : 2. Incidentally, R can
be found naturally as a building block for proteins. It was noted that R does not have intramolecular
hydrogen bonding.
Suggest structures for M, P, Q and R, explaining how the identities you suggest t in with the
experimental observations described above.
5. (VJC2011/P3/Q4(b))
D (C
10
H
8
O
2
) is a neutral compound. On heating with aqueous NaOH followed by acidication, D
yields only one organic product, E (C
10
H
10
O
3
), which is soluble in aqueous Na
2
CO
3
. When E is
treated with H
2
and Ni, F (C
10
H
12
O
3
) is formed. Unlike E, F does not display cis-trans isomerism.
1 mol of F is found to decolorize exactly 2 mol of aqueous Br
2
. Upon reaction with LiAlH
4
in dry
ether, F forms the compound G. G is no longer soluble in Na
2
CO
3
. When G is passed over hot Al
2
O
3
,
H is produced.
H reacts with gaseous HCl to give the major product I, which exists as optical isomers. On warming
I with aqueous AgNO
3
, aw white precipitate is formed together with an organic product which does
not change the colour of acidied K
2
Cr
2
O
7
solution.
Deduce the structures of all the lettered compounds (D to I) and explain the reactions involved.
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