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EH/OCT 2008/CHE495

UNIVERSITI TEKNOLOGI MARA FINAL EXAMINATION

COURSE COURSE CODE EXAMINATION TIME

HYDROCARBON CHEMISTRY CHE495 OCTOBER 2008 3 HOURS

INSTRUCTIONS TO CANDIDATES 1. 2. 3. This question paper consists of FIVE (5) questions. Answer ALL questions in the Answer Booklet. Start each answer on a new page. 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: ) ) ) the Question Paper t w o - pages Appendix an Answer Booklet - provided by the Faculty

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


This examination paper consists of 6 printed pages
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EH/OCT 2008/CHE495

QUESTION 1 a) Convert all the 4 formulas into 10 line-bond structures that are consistence with valence rules. i) ii) iii) iv) C3H8 C3H7Br (2 possibilities) C2H40 (3 possibilities) C3H9N (4 possibilities)

(10 marks)

b) Draw the structure of the following names and show why they are incorrect: Write the correct name. i) ii) cis- 1,5-Dimethylcyclohexane 2-lsopropyl-4-methylheptane (6 marks) c) Give the ground-state electron configuration for each of the following elements: i) ii) Potassium (Number atoms : 19) Sulfur (Number atoms : 16) (4 marks)

QUESTION 2 a) The IR spectrum of phenylacetylene is shown in Figure 1. Identify at least 4 absorption bands, (refer appendix: Table 1 )
4
I

5
f .

Wavelength \fim) 6 7 8 9 10
L__ L U L

4CKX

3500

3000 2600 2200 2000 1800 1600 1400 1200 1000 Wavenumber fcni" 1 ;

800

600

Figure 1: The IR spectrum of phenylacetylene. (6 marks)

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b) Nitriles, R-C=s=N, undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the compound produce by hydrolysis of propanenitrile, CH3CH2C=s=N, if it has IR absorption at 2500 cm"1 and 1710 cm"1, and Mw = 74 g/mol. (refer appendix: Table 1 ) (4 marks) c) Grinard reagents undergo a general and very useful reaction with ketones. Methylmagnesium bromide, for example, reacts with cyclohexane to yield a product with a formula C 7 H 14 0. What is the structure of this product if it has IR absorption at 3400 cm "1? (refer appendix: Table 1) (2 marks) d) Convert the following IR absorption values from micrometers to wave number and vice versa: (refer appendix: Table 2) i) ii) iii) iv) An An An An alcohol, 2.98 urn. ester, 5.81 urn. aldehyde, 1725 cm"1 acid chloride, 1780 cm"1. (4 marks) e) Which one as higher energy, infrared radiation with A = 1.0 x 10 "6 m or an X ray with A = 3.0 x 10 "9 m? (refer appendix: Table 2) (4 marks) QUESTION 3 a) Identify the monomer units from which each of the following polymers is made, and state whether it is a chain-growth or a step growth polymer. ii) o-

W //

o\ c/
iv) 0

-o-

o ci

-^NHCHaCHaCHzC-k v)

-eCF,CFCi-b

-t-CH, O-fc
(10 marks)

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b) Define the terms below: i) ii) isotactic atactic (3 marks)

c) Zieler -Natta catalyst is form from many formulations; it has vast advantages, give 2 advantages of the Ziegler-Natta polymers. (4 marks) d) Copolymers are obtained when two or more different monomers are allowed to polymerize together. Draw the copolymer structure of the terms mentioned below: i) ii) iii) Random copolymer, Alternating copolymer, Graft copolymer (3 marks) QUESTION 4

a) How would you prepare the following alkyl halides from the corresponding alcohols? i) ii)

CI I
CHgCCHg CH3 b) Give IUPAC names for the following alkyl halides: i) CH, ii)

Br

CH3

! CH 3 CHCH 2 CHCH 3
(4 marks)

CHHG\ v. I I ^
2
2

CHaCCHoCHjyCl

I
CI

CH :1 CHCHCH,CH ; .
(3 marks)

c) Draw the structures corresponding to the following names: i) ii) 3-Methylbutanal 4-Ch!oro-2-pentanone (4 marks)

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d) How would you carry out the following reactions? More than one step may be required. i) 3-Hexyne -> 3-Hexanone (2 marks) ii) Bromobenzene -> m - Bromoacetophenone (5 marks) e) Names the following aldehyde: o
CH3CHs.CCHCH3

(2 marks) QUESTION 5 a) The following cycloalkenes gives a mixture of two alcohols on hydroboration followed by oxidation. Draw the structure of the intermediates upon hydroboration and the final product of oxidation. Discuss the possibilities of the intermediates and final product structures.

H 3 C-

(10 marks) b) What product would you obtain from Claisen condensation of 2 Ethyl propanoate? (4 marks) c) Show the product you would obtain by reduction of the following esters with LiAIH4.
II

f,

":^

(3 marks)

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d) Draw the structure of the acetal you would obtain by acid-catalyzed reaction of 2-pentanone with propane-1, 3-diol.

(3 marks)

END OF QUESTION PAPER

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CONFIDENTIAL Formula List

APPENDIX 1

EH/OCT 2008/CHE495

Table 1: Characteristic IR Absorptions of Some Functional Groups

Intercity of Functional group class Aikanes. alkyl groups C-H Alkenes =CH Band position (cr~*) 2850-2960 3020-3100 1640-1680 3300 2100-2260 600-800 500-600 500 3400-3650 1050-1130

absrrption
Medium to st roa g Medium Medium Strong Medium Strong Strong Strong Strong, broad Strong

c=c

Alkynes

Alkyl halides CBr C-4 Alcohols

c-a

C-0
Aronaatics
* /

3030

Weak

1660-2000

Weak Medium Medium Medium Strong Strong, very broad Medium Strong

!
Aminee N-H CN

I!
1450-1600 3300-3600 1030-1230 1670-1780 2500-3100 2210-2260

Carbonyl compounds*

c=o
Carboxylic acids O-H Nitriles Nitro compounds NO,

1540

"CartiQXViHs acsste. esteu. aldehydes, aad ketsaes

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APPENDIX 2

EH/OCT 2008/CHE495

Table 2: The amount of energy he e = hv = X

x = cV

Where: e = Energy of 1 photon (1 quantum) 34 34 /7 = Planck's constant (6.62 x 10 " J.s = 1.58 x10 " cal.s) = = 1 V- = Frequency (s " ) A--= Wavelength (m) = c = Speed of light ( 3.00 x 108 m/s)

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