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Across the spectrum
Y13 UNIT 4 TEST 7
4.10 ORGANIC SYNTHESIS AND ANALYSIS
4.11 STRUCTURE DETERMINATION
Answer a !"es#$%ns
GOOD LUC&'
Answer all questions
Total 54 marks
Na(e)**********************.
Mar+ ,%r Se-#$%n A*****.3/
Mar+ ,%r se-#$%n ***** 1
T%#a) ***********. 4
Gra2e**..
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SECTION A
1. This question concerns four isomers, W, X, Y and Z, with the
molecular formula C5H10O2
(a) The proton n.m.r. spectrum of W shows pea!s.
The ta"le "elow #i$es the chemical shifts, % $alues, for each of
these pea!s, to#ether with
their splittin# patterns and inte#ration $alues.
%&ppm 2.1' 2.5 . .*
+plittin# pattern sin#let triplet sin#let triplet
nte#ration $alue 2 2
+tate what can "e deduced a"out the structure of W from the
presence of the followin# in
its n.m.r. spectrum.
(i) The sin#let pea! at % - 2.1'
...........................................................................................................................
(ii) The sin#let pea! at % - .
...........................................................................................................................
(iii) Two triplet pea!s.
...........................................................................................................................
(i$) Hence, deduce the structure of W.
(4)
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(b) The infra-red spectrum of X is shown below.
1 0 0
5 0
0
T
ra
n
sm
itta
n
c
e
&.
0 0 0 ) 0 0 0 2 0 0 0 1 5 0 0 1 0 0 0 5 0 0
/ a $ e n u m " e r & c m 1
(i) /hat can "e deduced from the "road a"sorption centred on 000
cm1
in the infra
red spectrum of X
...........................................................................................................................
(ii) 3i$en that the proton n.m.r. spectrum of X contains onl4
two pea!s with the
inte#ration ratio 1, deduce the structure of X.
(2)
(c) somers Y and Z ha$e the structures shown "elow.
C H )
C H )
CC
O
H C O H)
Y
C
O
H C) C H C O H
C H )
H
Z
2
dentif4 the two rea#ents 4ou could use in a simple chemical test
to distin#uish "etween
Y and Z. +tate what 4ou would o"ser$e when each of Y and Z is
tested with a mi6ture of
these two rea#ents.
Reagents
..................................................................................................................
Observation with
Y......................................................................................................
Observation
withZ......................................................................................................(3)
(Total 9 marks)
2. Compounds Cand D, shown "elow, are isomers of C5H10O
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H C C C H C H C H
O
2 2 ))
2
2
2
2
H C
H CC
C
C
H
H
H
O H
C 7
(a) 8ame compound C.
.....................9999999999999999999999999999.(1)
(") :se Table 2 on the 7ata +heet to help 4ou to answer this
question.
(i) +u##est the wa$enum"er of an a"sorption which is present in
the infrared
spectrum of C"ut not in that of D.
...........9999999999999999999999999999.
(ii) +u##est the wa$enum"er of an a"sorption which is present in
the infrared
spectrum of D"ut not in that of C.
...........9999999999999999999999999999.(2)
(c) 7educe the num"er of pea!s in the proton n.m.r. spectrum of
C.
.....................9999999999999999999999999999.(1)
(d) dentif4 a rea#ent that 4ou could use to distin#uish "etween
Cand D. ;or each of Cand
D, state what 4ou would o"ser$e when the compound is treated
with this rea#ent.
Reagent 99999999999..999999999999999999..
Observation with C 9999999999999999999999999..
Observation with D9999999999999999999999999..(3)
(e) Compound E, CHCH2CH2CH2CHO, is also an isomer of C5H10O
dentif4 a rea#ent which will react with E"ut not with Cor D.
+tate what 4ou would
o"ser$e whenEis treated with this rea#ent.
Reagent 99999999999..999999999999999999..
Observation with E 9999999999999999999999999..(2)
(Total 9 marks)
3.
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7raw one possi"le structure for each of the species A to J,
usin# Ta"le 2 on the 7ata +heet
where appropriate.
(a) Compounds A and B ha$e the molecular formula C5H10A
decolourises "romine water "ut B does not.
A B
(2)
(") Compounds C and D ha$e the molecular formula C2HO2
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4. The proton n.m.r. spectrum of an organic compound F, C4H8O,
is shown below.
) 2 1 0& p p m
The measured inte#ration trace #i$es the ratio 0.5 to 0.=5 to
0.=5 for the pea!s at 2.=, 2.15
and 1.05, respecti$el4. The infrared spectrum of compound F has
an intense "and at
1=15 cm1
. n the mass spectrum of F$ dominant fra#mentation pea!s appear
at
m&z- and m&z- 5=.
(a) 3i$e the structural formula of the compound responsi"le for
the si#nal at 0.00 in the
n.m.r. spectrum.
(1)
(") How man4 different t4pes of proton are present in compound
F
...................................................................................................................................(1)
(c) /hat is the ratio of the num"ers of each t4pe of proton
...................................................................................................................................(1)
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(d) /hich al!4l #roup is responsi"le for the si#nal at 2.15 in
the n.m.r. spectrum
...................................................................................................................................(1)
(e) The pea!s at a 2.= and a 1.05 arise from one #roup in
compound F. dentif4 this #roup
and e6plain the appearance of the splittin# pattern shown in the
n.m.r. spectrum.
Group..........................................................................................................................
Explanation
................................................................................................................
...................................................................................................................................
...................................................................................................................................(3)
(f) /hich #roup is responsi"le for the "and at 1=15 cm1
in the infrared spectrum of
compound F
...................................................................................................................................(1)
(#) 3i$e the structures of the species responsi"le for the pea!s
at m&> $alues of and 5= in
the mass spectrum.
Peak at m&z =
43.........................................................................................................
Peak at m/z =
5.........................................................................................................(2)
(h) 3i$e the structure of compound F.
...................................................................................................................................(1)
(Total 11 marks)
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SECTION B
%. (a) 7escri"e how propanal, CHCH2CHO, and propanone, CHCOCH,
can "e distin#uished
usin#
(i) a chemical test and
(ii) the num"er of pea!s in their proton n.m.r. spectra.(%)
(") Compound Z can "e produced "4 the reaction of compound X
with compound Y as
shown in the s4nthesis outlined "elow.
C H C H C H O+ t e p 1
+ t e p 2C H C O C H
C H C H C
O
O C H
C H
C H
)
)
) )
) 2
2
)
+ t e p )
X
YZ
dentif4 compounds X and Y.
;or each of the three steps in the s4nthesis, name the t4pe of
reaction in$ol$ed and #i$e
rea#ents and conditions.
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