Spiing 2u14

1
!"#$ &'&
"()*+(,- .'/ 01* 23 34* 5*6788786 (9 :;2<< (8 =*5 >
(woith 2u pts, 1 ptpioblem)

07,*:37(8</ '? @,(A7B* C(1, 28<+*,< (8 2 <:283,(8 D+7;; 5* 2A27;25;* 78 :;2<<E
&? F* +7;; 6,2B* (8;C 34* <:283,(8<
>? @13 C(1, 82)* 28B <31B*83 G0 . (8 34* <:283,(8
H? I<* 2 .& J*8:7; 9(, 34* <:283,(8
K? F* +7;; 8(3 :(;;*:3 (, 6,2B* 347< <4**3L M1<3 34* <:283,(8
N? @,(A7B* (8;C (8* 28<+*, J*, O1*<37(8


1.

Aie the inuicateu piotons homotopic, enantiotopic, oi uiasteieotopic.



2.

Aie the inuicateu piotons homotopic, enantiotopic, oi uiasteieotopic.



S. Bow many signals will the following compounu exhibit in the
1
B NNR spectium.


4. Bow many signals will the following compounu exhibit in the
1
B NNR spectium.


H
H Cl
Cl
(a) homotopic
(b) enantiotopic
(c) diastereotopic
H
N
H
N
H H
(a) homotopic
(b) enantiotopic
(c) diastereotopic
OH
OH
(a) 10 (d) 4
(b) 2 (e) 6
(c) 1
CH
3
CH
3
CH
3
(a) 4 (d) 12
(b) 2 (e) 3
(c) 9
*82837(3(J7:
4()(3(J7:
H
H
Spiing 2u14
2
S. Which of the following techniques coulu best uistinguish between compounus '
anu &.


6. In the
1
B NNR spectium, the splitting pattein of the pioton maikeu "a" will be a:


(a) tiiplet (u) quintet
(b) quaitet (e) multiplet
(c) uoublet of uoublets

7. In the
1
B NNR spectium, the splitting pattein of the pioton maikeu "b" will be a:


(a) singlet (u) tiiplet
(b) B(15;*3 (e) quaitet
(c) uoublet of uoublets

8. 0f statements (a) - (u), which is N0T tiue. If all aie tiue, choose option (e).

(a) IR light incieases the vibiations of IR-active bonus
(b) Symmetiical alkynes aie not IR-active
(c) Caiboxylic acius anu alcohols both exhibit bioau IR stietches foi the 0B bonu
DBE P4* 9786*,J,783 ,*67(8 7< 34* )(<3 1<*91; ,*67(8 78 28 GQ <J*:3,1) 9(,
7B*8379C786 918:37(82; 6,(1J<
(e) Statements (a)-(u) aie all tiue

9. Tiue oi false. In a
1S
C spectium, the total numbei of peaks coiiesponus to the total
numbei of caibons in a molecule.

(a) tiue (b) 92;<*


1u. Tiue oi false. In a mass spectium, the paient ion is not always piesent:

(a) 3,1* (b) false



O
O
Compound 1 Compound 2
(a) IR
(b)
1
H NMR
(c)
13
C NMR
(d) UV/vis
(e) none
O
O
H
H
Br "a"
O
O
H
H
Br
"b"
'
" R$Q
:()J;*S
<J;733786L
34*,*9(,*/
)1;37J;*3
Spiing 2u14
S
11. Bow many signals will the following compounu exhibit in the
1S
C NNR spectium.




12. The stiuctuie of piopyl benzoate is shown below with each pioton labeleu. In the

1
B NNR spectium shown, which pioton coiiesponus to the peak at ~4.2 ppm.



(a) a (u) u
(b) b
(c) c







N N
O
(a) 6 (d) 8
(b) 7 (e) 4
(c) 5
O
O
a
b
c
d
T
5
Spiing 2u14
4
1S. An unknown compounu has a mass of 1u8 gmol anu exhibits the mass spectium
shown below. Baseu on the mass spectium, you can concluue that the unknown
molecule contains which of the following functional gioups.



(a) 2 :4;(,78* 23() (u) both (a) anu (c)
(b) a biomine atom (e) none of the above
(c) a benzene iing






















Spiing 2u14
S
Questions 14-2u peitain to the same unknown compounu.

14. Baseu on the following IR spectium, which functionality uoes the unknown
compounu contain.



(a) a caiboxylic aciu (u) an alcohol
(b) 2 :2,5(8C; (e) a nitiile
(c) an amiue


1S. Baseu on the IR spectium in question 14, which auuitional functionality uoes the
compounu contain.

(a) an alkyne (u) a teitiaiy amine
(b) an alkene (e) 28 2;-28*
(c) an ethei

















1S69
1Su9
1766
1217
2967
1u12
967
911
P4* '&'T J*2- :(1;B <166*<3 28
*34*,L 513 3423 ,*67(8 :(1;B
:(,,*<J(8B 3( (34*, <3,*3:4786
)(B*< 2< +*;;L <( 73U< 8(3 :(8:;1<7A*?
Q*)*)5*,L 282;CV* 34* 918:37(82;
6,(1J ,*67(8L 8(3 34* 9786*,J,783
,*67(8?

I;37)23*;CL +* 62A* :,*B73 9(, : 28B
*?
Spiing 2u14
6


16. Baseu on the
1
B NNR spectium below, how many methyl gioups aie in the
unknown compounu that gave iise to the spectium.

(a) one (u) foui
(b) 3+( (e) zeio
(c) thiee




17. Baseu on the
1
B NNR spectium in question 16, how many methylene gioups aie in
the unknown compounu that gave iise to the spectium. (Remembei, a methylene
is -CB2-).

(a) (8* (u) foui
(b) two (e) zeio
(c) thiee








t
SB
s
SB
q
2B
u
2B
u
2B

Spiing 2u14
7
18. Baseu on the
1
B NNR spectium in question 16, the compounu must contain:

D2E 2 B7W<15<37313*B 5*8V*8* ,786 +734 <15<373137(8 23 34* 'W 28B HWJ(<737(8<
(b) a mono-substituteu benzene iing
(c) a tii-substituteu benzene iing
(u) a ui-substituteu benzene iing with substitution at the 1- anu 2-positions
(e) none of the above

19. Baseu on the
1
B NNR spectium question 16, the compounu also must contain:

(a) an ethyl ethei
D5E 2 )*34C;*8* :(88*:3*B 3( 28 2,()237: ,786
(c) an alcohol connecteu to an aiomatic iing
(u) a methylene connecteu to an alcohol
(e) none of the above

2u. Baseu on the infoimation pioviueu in questions 14-19, the stiuctuie of the
unknown compounu is:



O
O
O
O
O
OH
O
OH
O
O
(a)
(b)
(c)
(d)
(e)
5