(IIIICC•,

suppl 11cnt
s

CHEM 121: lNTROlll'CTION TO ORGANIC CHEMISTRY

rime: 3 Hours (lot~I masks_ 7QJ
Ins ructions: Ans\ver all 1hc qucs_ti.l.~in=s__

Question One
(a) Regarding c,Hbon and the simplest organic compound m,,thane, Cl 1,,
1
\,\,'rite Jo,rn the "round
b state electronic configuration of carbon. [ mar
mark
(i) Sketch dit1grtuns of the three types of degenerate p-orbitals. [3
(ii) [1
I1,n1· do p-orbitals differ from s orbitals?
(iii) Using the concept of molecular hybridization, describe how the carbon at ~ a,
(i\') methane (CH,) is able to form four sigma bonds with four hydrogen ato~t
.,. . Hmar
, 10\v t 1e 1y nu1zat1on of the carbon atoms labelled a-fin the compound be!
SI 1 I b [3 mar

d
f

a 0

(b) State four characteristics of a I,omo1ogous series such as alkanes. [2 mark

. orde I· of mcreasing
(c) Arrange compou11ds 1.-v 1. m · boili11a .
b pomt. [2 112 mar

~ (1)
I (ii) (iii)

~ ~
(iv) (v)
(\ i)

(d) Give the strutura

(i) 2,2,3 ~-t cl formula of:
.. ' etrainetl
(u) 1,2-dibroin 2 1ylpentane
o- -meth ylpropane
 of the followm 01 1 anic compound [4

I
l)iaJtililgtll
(1v)

h between a nudL'ophik and ,rn electrophile and give example in each

[1 Marks]

ll'l:,u.•it; M rk )rn1ko, s rule and use an appropriate example to demonstrate [2 Marks]

Prc,vicle product and the ,1ppwpri,1te mechanism for the following reaction
[1 Marks]

H (H CH( H, IIBr

the product(s) ot the tollovving rec1ctions

Poisoned
')
I I,
Pd/C catalyst [1 Mark]
1)
')
2Br 2 [1 Mark]
(11)

(0 PrO\ ide the structure of the following aromatic compounds

(1) Toluene [1 Mark]

(ii) Para-Xvlene [I Ma1kJ

(g) Provide the product (s) of the tolhl\\ing reactions

HC-C
//
Cl

/1 (Vld
 CH CH2CH2CH 2OH + HBr ►

CH 3

(1i) H3C-C-OH
I + HBr ►

I
CH 3
[2½ marks)

Question Four

(a) Name the follo\\ ing compounds according to IUPAC system of nomenclature.
[6 marks]
0

(1) ~H
0
(1i)~
0
(iii) ¢ F

0 0
(v)~OH
(1v) ~a/' / (vi)~H
I o 0
[3 Marks]
(b) Ora\\- the structures of the following compounds.

(i) 4-Meth) lnon-4-onc

(ii) 4-Meth) lhex-3-cn-2-one
(iii) 2-brom ocycl ohenzcnaldehyde

(c) Explain why the boiling point of 1-pentanol is higher than that ofpentanal.
[ 1 ½ marks]

(d) Write dovvn the major reagents required to effect the following conversions.
[2 mark-- I

p I,; .. , "I
 I 'r • 20 111 21121)
l 111\1.'1,,1, ·' I j I"" 1..

"lijlpll.'lllL 11lc11: "lpec 1,tl l'\,1111'

t 111 \I 121

(I.') Stud) th1.' rl'dlliLHl -,c\lL·nw b1. l,m <111J .111,\\L'I the quc~t1011~ 1ha11 11 110,,

1) L1AIH 4 PCC
A + -- B Process 3
H• 2) H30•
Process 1 Process 2

ti) Dra,, the structures of compounds A and B [2 marks]

( 11) Name process 1. 2 and 3 [3 marks]

THE END