FEDERAL PUBLIC SERVICE COMMISSION

COMPETITIVE EXAMINATION FOR RECRUITMENT TO POSTS IN BS-17 UNDER THE FEDERAL GOVERNMENT, 2011 CHEMISTRY, PAPER-II
30 MINUTES MAXIMUM MARKS: 20 TIME ALLOWED: (PART-I MCQs) THREE HOURS (PART-II) 2 HOURS & 30 MINUTES MAXIMUM MARKS: 80 NOTE: (i) First attempt PART-I (MCQs) on separate Answer Sheet which shall be taken back after 30 minutes. (ii) Use of simple calculator is allowed. (iii) Overwriting/cutting of the options/answers will not be given credit. (PART-I MCQs) (COMPULSORY) Q.1. (i) Select the best option/answer and fill in the appropriate box on the Answer Sheet. Carbon atoms in p-xylene are: (a) (ii) (iii) sp 2 hybridized Lactose (b) sp 3 hybridized Sucrose (c) Sp hybridized (d) Both (a) and (b) (1 x 20=20)
Roll Number

Which of the following sugars is found in milk? (a) (b) (c) Maltose (d) Fructose Glucose when heated with Benedicts reagent (CuSO 4 , NaOH, and tartaric acid) forms a brick red precipitate due to formation of: (a) Cu 2 O Methanol Chiral compounds Pyrrole (b) Cu(OH) 2 Ethanol
Unsaturated compounds

(c)

Copper tartrate

(d)

None of these

(iv) (v) (vi) (vii)

Which of the following can not be used as solvent in polarimetry? (a) (a) (a) (b)
(b)

(c) (c) (c)

1-butanol Polar compounds Furan O

(d) (d) (d)

2-butanol All of these Piperidine

Polarimetry is a technique to analyze: Which of the following is not an aromatic compound? (b) Pyridine Which of the following is not a heterocyclic compound? (a) N (c) O (d) S (b) (d) 3,4-dimethylhexane 1,4-dimethylcyclohexane (b)

(viii) Which of the following will show optical isomerism? (a) (c) (ix) 2,3-dimethylbutane 3,4-diethylhexane

What type of reaction takes place when a ketone is treated with HCN? (a) (c) Electrophilic substitution Nucleophilic addition (b) (d) Nucleophilic substitution Electrophilic addition

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CHEMISTRY, PAPER-II
(x) What is the major product in the following reaction?

excess CH 3 OH H 2 SO4
(a) OCH 3 (b) OCH 3

(c) (xi)

(d)

OCH 3 OCH 3

What are the expected products from the following reactions?

1) O3 2) Zn, H 3O
(a) (c) 2 (xii) Which of the following will undergo Aldol condensation? (a) (a) (a) (c) (xv) Formaldehyde Ethanol Aniline N,N-dimethylaniline Reagent (a) (b) (c) (d) Na Metal (C 6 H 5 ) 3 P = C(C 2 H 5 ) 2 KOH/NH 2 -NH 2 Se + 250 C CH 3 H Br CH 3 (a) 2R, 3R (b) 2R, 3S (c) 2S, 3R (d) 2S, 3S (xvii) The reaction acetone with phosphonium ylide [(C 6 H 5 ) 3 P = C(CH 3 ) 2 ] produces: (a) (c) 2,3-dimethyl-2-butanol 2-chloro-2,3-dimethylbutane (b) (d) 2,3-dimethyl-2-butene Both (a) and (b) OH H Reaction Witting reaction Wurtz reaction Wolff-Kishner reduction Birch reduction (b) (b) Acetaldehyde Butanol (c) (c) (b) (d) Benzaldehyde Cyclohexanol m-chloroaniline m-nitroaniline (d) (d) All of these Phenol + H (d) 2 H (b) + H

(xiii) Which of the following is the most acidic? (xiv) Which of the following is the most basic?

Which of the following are correctly matched?

(xvi) What is the correct configuration at chiral centers in the following molecule?

(xviii) Which of the following reactions are used to prepare amines: (a) Gabrial synthesis (b) Hofmann reaction (c) Reductive amination (d) All of these Page 2 of 4

CHEMISTRY, PAPER-II
(xix) The active agent in the nitration of benzene is: (a) (xx) NO 2

(b)

NO 2

(c)

NO

(d)

HNO 2

The most probable intermediate in Favorskii rearrangement is: (a) Lactone (b) Lactam (c) Cycloprapanone (d) None of these

PART-II
NOTE:(i) (ii) (iii) PART-II is to be attempted on separate Answer Book. Attempt ONLY FOUR questions from PART-II. All questions carry EQUAL marks. Extra attempt of any question or any part of the attempted question will not be considered. Differentiate between Inter-molecular and Intra-molecular hydrogen bonding. Discuss effects of hydrogen bonding on any two properties of organic compounds. Support your answer with suitable examples. (08)

Q.2. (a)

(b)

Arrange following compounds in decreasing order of their base strength (strongest first). (03) Give a brief explanation in support of your answer:

N H3

NH 2

CH 3 N H 3

CH 3 N H 2
40

N H4 N H3 9 36 5 18 (06)

pK a values 11 (c)

How would you account for the following: i. Picric acid (2,4,6-trinitrophenol) liberates CO 2 from aqueous soulution of Na 2 CO 3 but phenol does not? ii. Benzene undergo Friedel Craft alkylation in the presence of Lewis acid while pyridine does not? iii. Benzene is an aromatic compound while cyclooctatraene is nonaromatic? Discuss how a catalyst changes the rate and path of the reaction? Reaction of 1, 3-butadiene with HBr gives two products, draw reaction coordinate diagram to illustrate thermodynamic and kinetic products of the reaction. For the following reaction: CH 3 (CH 2 ) 3 Br + OH CH 3 ( CH 2 ) 3 OH + Br Discuss rate law and various factors that affect the rate of reaction. Starting from benzene how would you prepare the following compounds: Benzoic acid, 4-Bromonitobenzene, Maleic anhydride Show reaction of C 2 H 5 MgBr with each of the following: i. ii. iii. CH 3 CHO followed by hydrolysis CH 3 C C H followed by reaction with CH 3 I CH 3 COOC 2 H 5 followed by hydrolysis.

Q.3. (a) (b) (c)

(06) (07) (07)

Q.4. (a) (b)

(06) (06)

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CHEMISTRY, PAPER-II
(c) Assign hybridization at each carbon in the following compound: (04)

CH 2
C

CH 2
CH 3 CH 3
C CH CH C C

CH

CH 3
CH

CH 2
CH C

CH 2

CH 3

CH 3

H 3C

CH 3

(d)

Suggest two methods to prepare aromatic amines. Discuss stereoisomerism in compounds having 2-similar asymmetric carbon atoms. Draw Fisher projection formulae for the following compounds: i. R and S 2 - bromopentane ii. R and S 3 - chloro-1-pentene iii. R and S 3 - chloro-3-methyloctane iv. R and S 2 - pentanol What do you understand by the terms Z and E isomer? Illustrate your answer by quoting suitable examples. Illustrate giving suitable examples the difference between Homogenous and Heterogeneous catalysis. Outline synthesis of azo dye starting with phenol and a suitable aromatic amine. Write notes on the following: i. Octane number ii. Catalytic cracking

(04) (06) (08)

Q.5. (a)
(b)

(c)

(06) (06) (04)

Q.6. (a)
(b) (c)

(05+ 05 = 10) (2 x 10 =20)

Q.7. Write structure of product(s) obtained from each of the following reactions:
i. ii. iii. iv. v. vi. vii) viii) ix) x) CH 3 CH 2 COOH + CH 3 CH 2 OH + H 2 SO 4 C 6 H 5 COCH 3 +LiAlH 4 C 6 H 5 COOH+ SOCl 2 (CH 3 ) 3 CBr + NaOH(aq) C 6 H 5 NH 2 + NaNO 2 + HCl (conc)
5 CH 3 CH 2 COCH 3 2

1 )C H MgBr 2 ) H 3O

C 6 H 5 NO 2 + Sn/HCl C 6 H 6 + Na/NH 3 CH 3 CH = CH 2 + HBr CH 3 COCH 3 + NH 2 OH Write main steps in the formation of following polymers: (03 + 03 = 06) i. Nylon 6,6 and Polyester via Condensation Polymerization. ii. Polyethlene via Free Radical Polymerization. What are alkaloids, describe chemical properties and structure of any two alkaloids. (07) Differentiate between oil, fat and wax. Draw structure of triglyceride containing oleic acid (06) [CH 3 (CH 2 ) 7 CH = CH ( CH 2 ) 7 COOH] as fatty acid and write reaction triglyceride with H 2 /Ni followed by NaOH(aq).

Q.8. (a)

(b) (c)

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