BKF1323-ORGANIC CHEMISTRY 21213.PDF

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Universiti

Malaysia

P H NG

nIneeiing

reatMty

FACULTY OF CHEMICAL NATURAL RESOURCES ENGINEERING

FINAL EXAMINATION

COURSE RGANIC CHEMISTRY

COURSE

CODE

KF1323

LECTURER

BDUL AZIZ MOHD AZODDEIN

CHE KU MOIIAMMAD FA IZAL BIN CHE

KU

YAHYA

DATE

9 JUNE 2013

DURATION

HOURS

SESSION/SEMESTER

ESSION 2012/2013 SEMEST ER II

PROGRAMME CODE

KB/BKC/BKG

INSTRUCTIONS TO CANDIDATE:

1 This question paper con sists of

FOUR 4)

questions Answer ALL questions

2

All answers to a new question should start on new page

3

All the calculations and assumptions must be clearly stated

4

Candidates are not allowed to bring any material other than those allowed by

the invigilator into the exam ination room

EXAMINATION REQUIREMENTS: -

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

This examination paper consists of

EIGHT 8)

printed pages including front page



CONFIDENTIAL

BKBIBKC/BKG/121311JBKF1323

QUESTION 1

a Give the IUPAC names for the following compounds.

i

1 Mark)

ii

iii

1 Mark)

8r

r

1 Mark)

iv

r

1 Mark)

V

1 Mark)



CONFIDENTIAL

BKB BKC BKG 1213111BKF1323

vi

Br

H

1 Mark)

b)

raw structures corresponding to the following TUPAC names:

i)

5-bromo-3-propylhex- 1 -ene

1 Mark)

ii)

5-chloro-4-methyl-2-hydroxy-hex-3-ene

1 Mark)

iii)

4,4,4-trifluorobut- 1 -ene

1 Mark)

iv )

2-methylbut-3 -enal

1 Mark)

v) Toluene

1 Mark)

C)

hat is the correct oxidation-level ordering of the following compounds, staring

will lowest oxidation level?

A: CH 0 B: HO)

C 0

: H

CO D: CH4

2 Marks)

d)

rrange the following phenols in order of increasing acidity least to most).

3



CONFIDENTIAL

BKB/BKC/BKG/121311/BKF

1323

ct:, C N

NO

2

NH2

C

D

2 Marks)

e)

ydrocarbon A C

7H )

was treated with BH

3

followed by H

0

INaOH to provide

B C

7

H

4

0) as the only product. Reaction of B w ith TsC1/pyridine followed by

KOH gives C isomer with A) in addition to other olefin s). Treatment of C with

ozone followed by Zn/AcOH produces only the compound shown:

H3CY ̂ ^^CHO

CHO

i)

What is the correct formula for A?

ii)

What is the correct formula for B?

iii)

What is the correct formula for C?

6 Marks)

f)

ank the following in order of stability lowest to highest):

4 Marks)



CONFIDENTIAL

BKB BKC BKG 121311 BKF1323

QUESTION

2

a) Draw the molecules structure of triethylamine and diisopropylamine.

4 Marks)

b) Explain the increasing in the boiling point of the organic compounds below.

CH 3 CH

20CH

CH

3

CH3CH2CH2CH2NH2

H3CH2CH2CH20H

4 Marks)

c) Using structure m olecules, explain wh y tertiary amines

30)

have lower boiling point

than 1

and 2° amines of comparable molecular weight.

4 Marks)

d If we compare an

alkylamine

and an

arylamine

we must look at the availability of the

nonbonded electron pair on N.

With CH

3

CH2

TT

for example, the electron pair is

localized on the N atom. Explain by describing the delocalized electron pair on the

benzene ring of an

wylamine

and what is the implication to the chemical properties

of amine.

8 Marks)

e Give an explanation for Hofmann elimination by showing the steps to synthesis

propene from propylamine.

5 Marks)



CONFIDENTIAL

BKBIBKCIBKG/1213111BKF1323

QUESTION 3

a The reaction of an aldehyde or ketone with Grignard reagent, RMgX is a

nucleophilic addition to the carbon-oxygen double bond. Based on your

understanding, answer the following question

i . Give the definition of nucleophile?

2 Marks)

ii .

What is the function of G rignard reagent in this reaction?

2 Marks)

iii .

What product is formed initially and product forms when water is added.

Show the mechanism to produce a both products.

6 Marks)

b

y using the suitable example, discuss about concept of inductive and re sonance

effect that effluent the location and rate of aromatic substitution reactions.

6 Marks)

C

raw a stepwise m echanism for the reaction below

H

CH

H

H2SO4

1120

a H

4 Marks)

d

rite out the steps describing the mechanism of the free-radical bromination of

methane. Classify each step as initiation, propagation or term ination.

5 Marks)

6



ii).

CH30H

2SO4

H20

CONFIDENTIAL

BKB/BKCIBKG/1213111BKF1323

QUESTION

a)

raw the organic products formed in each reaction

1

D-, ,^

Cr03

?

H2SO4/H20

2 Marks)

2 Marks)

iii).

Cr03

? ?

H2SO41H20

4 Marks)

iv).

[ ] cHI

excess)

]

Ag20

[3] Heat

2 Marks)

b)

nswer the following questions.

i . Give curved arrow mechanisms that show how both of the products A and

B of the following reaction are formed Indicate which is the major and

which the minor product.

7



CONFIDENTIAL

BKB BKC BKG 1213111BKF1323

r

HBr

C i

4 Marks)arks)

ii .

riefly explain why one of the products is major and the other minor.

4 Marks)

c

Draw a detailed mechanism for the chlorination of benzene using C1

and FeCl3.

4 Marks)

d

Explain why benzaldehyde is less reactive than cyclohexanecarbaldehyde towards

nucleophilic attack.

HO

C HO

benzaldehyde

cyclohexanecarbaldehyde

3 Marks)

END OF QUESTION PAPER

8

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BKF1323-ORGANIC CHEMISTRY 21213.PDF