CONFIDENTIAL AS/DEC 2019/CHM207

UNIVERSITI TEKNOLOGI MARA

FINAL EXAMINATION

COURSE ORGANIC CHEMISTRY

COURSE CODE CHM207

EXAMINATION DECEMBER 2019

TIME 2 HOURS

INSTRUCTIONS TO CANDIDATES

1. This question paper consists of eight (8) questions.

2. Answer ALL questions in the Answer Booklet. Start each answer on a new page.

3. Do not bring any material into the examination room unless permission is given by the
invigilator.

Please check to make sure that this examination pack consists of:

i) the Question Paper

ii) an Answer Booklet- provided by the Faculty

5. Answer ALL questions in English.

DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO

This examination paper consists of 7 printed pages
© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL
CONFIDENTIAL AS/DEC 2019/CHM207

QUESTION 1

Consider the following organic compound

OH

C(CH3)3

a) For each of the carbon which labelled as X and Y, determine:

i) type of hybridizations
ii) type of bonds (ct and/or 7t) formed
iii) bond angles around it
(3 marks)

b) Classify the electrophiles and nucleophiles from the following groups.

CI" CH3+CH2 BH3 NH3 H-Br H20

(3 marks)

QUESTION 2

a) Draw the structures of the following compounds.

i) 5-fe/t-butyl-3-ethyloctane
ii) 4-/sopropylheptane
iii) 1,1,2-trimethylcyclopentane
(3 marks)

b) Write the propagation steps for the monochlorination of cyclohexane.

(3 marks)

© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL

CONFIDENTIAL AS/DEC 2019/CHM207

QUESTION 3

a) In electrophilic addition reaction, the electrophile adds preferentially to the sp2 carbon
bonded to the most hydrogens. Identify the suitable alkene that should be used to
synthesize each of the following alkyl bromides below.

Br

•CH2CHCH3 C(CH3)3Br

alkyl bromide alkyl bromide II

CH3

C CH3

CH2CH3
Br

alkyl bromide III alkyl bromide IV

(4 marks)

b) Draw the structure ofthe major product (compound A- D) for the following reactions.

LO3
H2, Pd/C 2. Zn, H30+
Compound D Compound A

CH2CH3
v. HCI, H20
HBr,
ROOR

T Compound B

Comp ound C

(4 marks)

© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL

CONFIDENTIAL AS/DEC 2019/CHM207

QUESTION 4

a) Name the following compounds using IUPAC system.

CH(CH3)2

compound E compound F

(2 marks)

b) Show the synthesis of compound F from benzene.

(5 marks)

QUESTION 5

a) Write complete structural chemical equation for the following Sw2 reactions.

i) c/s-1-bromo-4-methylcyclohexane and hydroxide ion

ii) fr-a/7s-1-iodo-4-ethylcyclohexane and methoxide ion
(6 marks)

b) Compose a complete S/v1 mechanism for the reaction below.

CH3 CH3

H3C C Br + H20 H3C C OH + HBr

CH3 CHc

(5 marks)

© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL

CONFIDENTIAL AS/DEC 2019/CHM207

QUESTION 6

a) Refer to the following questions.

i) Show the complete chemical reaction between phenol and water. From the equation,
state whether the solution is acidic or basic.
(2 marks)

ii) Determine the structure of compound G, Hand J to complete the reactions below.
Compound G

NaOH

HN03
phenol Compound H + Compound J

3Br2

Compound K
(4 marks)

b) Propose the synthesis steps for the product conversion below.

CH3

CH3C=CHCH3 / \ -C O CCH2CH3

CH3 CH,

(4 marks)

QUESTION 7

a) Compare the oxidation reaction of propanal and propanone with acidified potassium
dichromate (VI) solution (orange colour solution) in terms of its chemical reaction and
observation.
(5 marks)

)Hak Cipta Universiti Teknologi MARA CONFIDENTIAL

CONFIDENTIAL AS/DEC 2019/CHM207

b) The following reaction scheme is referred. Draw the structure of compound M, N and P.
O

II
(CH3)2CHCCH(CH3)2 compound M -• compound N
compound L HCN H20, H+

2,4-DNP

compound P

(3 marks)

QUESTION 8

a) Refer to the following questions.

i) Indicate reagents that would accomplish the following synthesis. More than one
reaction is required. Show the structural equation for the reactions.

benzaldehyde
J benzamide
J
(6 marks)

ii) Predict the major product for the following reactions.

EtOH
Reaction 1
CH3CH2CH2C—OH
cone. H+, heat

,COOH
LiAIH4
Reaction 2
H30+

^^
(4 marks)

© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL

CONFIDENTIAL AS/DEC 2019/CHM207

b) Draw structure of the products (compound Q, R, S and T) in following reaction scheme

below.

compound Q compound T
Nal

nitrous acid

compound R + compound S
Br2, FeBr3
^^
(5 marks)

END OF QUESTION PAPER

) Hak Cipta Universiti Teknologi MARA CONFIDENTIAL