QB MSc-I (Chemistry) Sem-I & II

CH-150: Basic Organic Chemistry (Sem-I)

Chapter 1- Stereochemistry
1 ....... is the most stable conformation of n-butane.
(a) Gauche (b) Fully eclipsed
(c) Anti or staggered (d) Partially eclipsed.
2 In structural representation of molecule the prefixes Z and E stands for ----
(a) Zigle- - Erythro (b) Zusammen- Estrogen
(c) Zeigle - Erhard d) Zusammen - Entgegen.
3 The priority sequence for the hydrogen isotopes is-----
(a) H > D > T (b) T>D>H
(c) H>T>D (d) D>T >H
4 Which of the following molecules have stereogenic ‘C’ atoms
(a) 1, 2-dichlorobutane (b)1,1,2 trichloropropane
c) 1, chloro 2 methyl cyclopentane (d) all of these.
5 According to CIP rules which of the following will have lowest priority
(a) –CH3 (b) –CH=CH2
(c) Deuterium (d) Tritium
6 Which of the following statement is true.
(a) Enantiomers are superimposable mirror images.
(b) The chair form is the least stable conformation of cyclohexane.
(c) In Fischer projection the tetrahedral carbon atom is projected in Such a way that
the horizontal bonds are below the plane and vertical bonds are above the plane.
(d) The two highest priority groups on the same side or the double bond has ‘Z’
configuration.
7 Double bond in 1,3 cyclohexadiene shows which form ?
(a) E (b) Z
(c) E and Z (d) none of these
8 The boat conformation of cyclohexane is less stable due to --- hydrogens.
(a) equatorial (b) axial
(c) Flagpole (d) none of these
9 ………… conformation of cyclohexane is free of angle strain and torsional strain.
(a) Boat (b) Twist boat
(c) Chair (d) Half chair

10 The correct order of stabiliiy of conformations of cyclohexane is…..

(a) Chair from > boat form > twist boat form
(b) Boat form > twist boot form > chair form.
(c) Chair form > twist boat form > boat form.
(d) Twist boat form > boat form > chair form.
11 The most unstable conformation of cyclohexane is----

(a) Chair (b) Half chair

(c) Twist chair (d) Boat
12 Which or following is Z isomer?

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13 An optically active compound

(a) must contain atleast four carbons
(b) when in solution rotate the plane of polarized light
(c) must always contain an asymmetric carbon atom
(d) in solution always give a negative reading in polarimeter
14 Alkenes show geometrical isomerism due to :
(a) Asymmetry (b) Rotation around a single bond
(c) Resonance (d) Restricted rotation around a double bond
15 A meso compound :
(a) is an achiral molecule which contains chiral carbons
(b) contains a plane of symmetry or a centre of symmetry
(c) is optically inactive
(d) is characterized by all of the above
16 Which of compounds have ‘R’ configuration

(a) I only (b) II only

(c) none of the above compound (d) both I and II
17 The following compound have…..configuration

(a) Z (b) E
(c) R (d) S
18 The correct configuration for following compounds is

(a) E, E (b) E, Z
(c) Z, Z (d) Z, E
19 In oxime, if the group with greater priority and the hydroxyl group are on the same
side of the double bond, the configuration is………, if on the opposite sides it
is………..
(a) R, S (b) E, Z
(c) Z, Z (d) Z, E
20 In gauche conformation of n- butane the dihedral angle between two methyl groups
is….
(a) 60 0 (b) 90 0
(c) 180 0 (d) 360 0

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21 The stability order for conformation of n-butane is…

(a) staggered > gauche > partially eclipsed > fully eclipsed
(b) fully eclipsed > partially eclipsed > gauche > staggered
(c) staggered > gauche > fully eclipsed > partially eclipsed
(d) partially eclipsed > gauche > staggered > fully eclipsed
22 In the following compound the configuration at C2 and C3 is

(a) R, S (b) S, R
(c) S, S (d) R, R

23 The following compound have…..configuration

(a) Z (b) E
(c) R (d) S
24 The following compound have…..configuration

(a) Z (b) E
(c) R (d) S
25 Which of the following compounds will show geometrical isomerism?
(a) CH2=CHCl2 (b) ClCH=CHBr
(c) CH2=CHCl (d) Cl2C=CBr2
Answers-

1) c 2) d 3) b 4) d 5) c
6) d 7) b 8) c 9) c 10) c
11) b 12) c 13) b 14) d 15) d
16) d 17) d 18) a 19) d 20) a
21) a 22) b 23) d 24) c 25) b

Chapter 2- Nucleophilic Substitution Reaction

1 In SN2 reaction there is….
(a) Partial racemization (b) complete racemization
(c) complete inversion (d) a little inversion and mostly racemisation
2 Vinyl halides and aryl halides are
(a) reluctant to SN1 only (b) reluctant to undergo SN 2 reaction only
(c) reluctant to SN1 as well as SN2 reaction
(d) favorable to SN 1 as well as SN2 reaction

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3 For SN2 reactions increase in solvent polarity

(a) increases rate of reaction ( b) decreases rate of reaction
(c) doesn’t alter rate of reaction (d) reaction stops
4 The observed reactivity sequence for halides in SN or SN2 is…
1

(a) R-I > R-Br > R-Cl > R-F (b) R-F > R- Cl > R-Br > R-I
(c) R-I > R- Cl > R-Br > R-F (d) R-I > R- F > R-Br > R-Cl
5 The rate of reaction SN 1 depends on
(a) the carbon skeleton (b) the leaving group
(c) solvent (d) all of above
6 An SN2 reaction goes with ……….. of configuration at carbon atom under the attack
but SN1 reaction generally goes with……….
(a) retention, inversion ( b) inversion, retention
(c) inversion, racemisation (d) retention, racemisation

7 The concentration of nucleophile….

(a) do not alter the rate of SN 1 and SN2 reaction (b) do not alter the rate of SN 1
(c) alters the rate of SN 2 reaction (d) both b and c

8 In the series,

The order of probability of SN 1 is …

(a) IV > III > II > I (b) IV > III > I > II
(c) III> II > I > IV (d) I > II > III > IV
9 In neighboring group participation product is obtained with….
(a) inversion (b) retention
(c) racemisation (d) none of these

10 In SNi mechanism rate of reaction is proportional to concentration of…

(a) alcohol only (b) SOCl2
(c) alcohol and thionyl chloride (d) substrate only

11 SN2 mechanism proceeds through intervention of…

(a) carbonium ion (b) transition state
(c) free radical (d) carbanion
12 Which of the following statement is false.
(a) In SN1 mechanism nucleophile attack in 2 nd step.
(b) In SN1 mechanism leaving group departs in 1 st step.
(c) In SN1 mechanism step 1 st is rate determining step.
(d) In SN1 mechanism nucleophile attack in 1 st step.
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 QB MSc-I (Chemistry) Sem-I & II

14

(a) 1-propanol (b) 1-propanol

(c) 1- chlorobutane (d) none of above
15 Which of the following statement regarding SN2 mechanism is wrong?

16 Which of the following statement regarding SN1 mechanism is wrong?

17 Which is the most reactive compound by the SN l mechanism?

18 Which of the following is most reactive as a nucleophile?

(a) PhO- (b) PhS-
(c) PhCH2O- (d) PhCH2NH2
19 Which of the following is least basic?
(a) PhO- (b) PhS-
(c) PhCH2O - (d) PhCH2NH2
20 Which is the main product of the following reaction?

21 Which is the main product of the following reaction?

22 Which of the following statements regarding nucleophilicity is wrong?

(a) Ethoxide ion is more nucleophilic than -butoxide in spite of its lower basicity.
(b) Ethoxide ion is more nucleophilic than t-butoxide due to the lower steric
hindrance.
(c) Chloride ion is more nucleophilic than iodide ion because of its higher basicity.
(d) Bromide ion is more nucleophilic than fluoride in spite of its lower basicity.
23 Which of the following is an ambident nucleophile?
(a) nitrite ion (b) cyanide ion
(c) phenoxide ion (d) all of these

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24 Which one of the following is aprotic polar solvent?

(a) H2O (b) DMSO
(c) Ethanol (d) Methanol
25 Which is the main product of the following reaction?

Answers-

1) c 2) c 3) b 4) a 5) d
6) c 7) d 8) a 9) b 10) c
11) b 12) d 13) d 14) d 15) d
16) c 17) c 18) b 19) b 20) a
21) b 22) c 23) d 24) b 25) a

Chapter 3- Electrophilic Substitution Reaction

1 Which gives a meta nitro compound as the main product upon nitration with a nitric
acid-sulfuric acid mixture?

2 In aromatic substitution reactions, attacking reagent is…

(a) Electrophile (b) Nucleophile
(c) Free radical (d) Both a and b
3 In Friedel-Craft’s acylation of an aromatic ring, the role of AlCl3 is to ….

(a) form (b) function as Lewis base

(c) hlorinate the aromatic ring (d) withdraw electrons from the ring
4 Benzene reacts with acetic anhydride in the presence of AlCl3 to form…..
(a) acetophenone (b) benzophenone
(c) phenyl acetic acid (d) phenyl acetate
5 In chlorination of benzene, FeCl3 is used to generate…..
a) Cl- b) Cl+ c) Cl2 d) HCl
6 Benzene undergoes substitution reaction more easily than addition because.
(a) it has a cyclic structure (b) it has three double bonds
(c) it has six hydrogen atoms (d) there is delocallization of
electrons
7 Which is most reactive in electrophilic substitution?

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8 Which is more reactive in electrophilic substitution?

9 Which will be the main product upon chlorination of m-nitrotoluene with

Cl2/AICI3?

10 Which one of the following is the drawback of F.C. alkylation?

(a) Polyalkylation (b) rearrangement
(c) Dealkylation (d) All of these
11 Benzene reacts with propene in presence of HCl and BF3, to produce…
(a) n-propyl benzene (b) Cumene
(c) benzophenone (d) nothing happens
12 For reactions of ethyl benzene, the ethyl group is considered as….
(a) ortho director (b)ortho-para director
(c) meta-director (d) ortho-meta director
13 Which gives a meta nitro compound as the main product upon nitration with a nitric
acid-sulfuric acid mixture?

14 Which will be the main product upon bromination of phenyl benzoate with
Br2/AlBr3?

15 Which is least reactive in electrophilic substitution?

16 Which of the following statements regarding Friedel-Crafts reactions is wrong?

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 QB MSc-I (Chemistry) Sem-I & II

(a) Alkylation of benzene with an alkyl chloride requires only a catalytic amount of
a Lewis acid such as aluminum chloride.
b) Alkylation of benzene with an alcohol requires only a catalytic amount of a
Bronsted acid such as phosphoric acid.
(c) Acetylation of benzene with acetyl chloride requires only a catalytic amount of a
Lewis acid.
(d) Acetylation of benzene with acetic anhydride requires m re tha one equivalent
of a Lewis acid
17 Which gives a para nitro compound as the main product upon nitration with a nitric
acid-sulfuric acid mixture?

18 Which gives a meta nitro compound as the main product upon nitration with a nitric
acid-sulfuric acid mixture?

19 Which of (a)-(d) does not give isopropylbenzene as a product upon reaction with
benzene?
(a) (CH3)2CHCl / AICl3 (b) CH3CH2CHCl / AICl3
(c) CH3CH=CH2 / H3PO4 (d) (CH3)2C=CH2 / H3PO4
20 Which pair of compounds are the most probable main products of the following
reaction?

21 Which of the following statements regarding electrophilic aromatic substitution is

wrong?
(a) Acetyl and cyano substituents are both deactivating and m-directing.
(b) Alkyl groups are activating and o,p-directing.
(c) Ammonio groups are m-directing but amino groups are and op-directing.
(d) Chloro and methoxy substituents are both deactivating and o.p-directing.
22 Diazonium cation can be obtained from.
(a) Primary aromatic amine (b) Aniline
(c) Secondary aromatic amine (d) Both a and b
23 P-chloro toluene on reaction with NaNH 2 and liquid ammona gives….
(a)p-amino toluene (b) m-amino toluene
(c)o-amino toluene (d) a and b both

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 QB MSc-I (Chemistry) Sem-I & II

24 Sulphonation of aromatic compounds cannot be carried out by…

(a) Conc. H2SO4 (b) Fuming H2SO4

(c) Dilute H2SO4 (d) Oleum
25 Which of the following statements regarding electrophilic aromatic substitution is
wrong?
(a) Sulfonation of toluene is reversible.
(b) Friedel-Crafts alkylation of benzene can be reversible.
(c) Friedel-Crafts alkylation with primary alkyl chloride may involve
rearrangement.
(d) Friedel-Crafts acylation of nitrobenzene readily gives a meta substitution
product.

Answers

1) c 2) d 3) a 4) a 5) b
6) d 7) b 8) d 9) a 10) d
11) b 12) b 13) b 14) c 15) c
16) c 17) c 18) d 19) d 20) a
21) d 22) d 23) d 24) c 25) d

Chapter 4- Addition Rection

1 Main product of the following reaction

2 Addition of one equivalent of Br 2 to 1,3-pentadiene produces….

a) 4,5-dibromo-2-pentene (b) 1,4-dibromo-2-pentene
(c) 3,4-dibromopentene (d) 3,4-dibromo-2-pentene
3 During addition of HX to alkene the formation of alkyl carbocation is…
a) Slow step b) Fast step
c) sometime slow and sometime fast d) cannot be predicted.
4 Addition of HX to alkene occurs by..
a) Peroxide effect b) Anti Markownikoff's rule
c) Inductive effect d) Markowmikoff's nule
5 Which of the following is the predominant product in the reaction of HOBr with
propene ?
(a) 2-Bromo-1-propanol (b) 3-Bromo-1-propanol
(c) 2-Bromo-2-propanol (d) 1-Bromo-2-propanol
6 During addition of HOX to alkene…
a) OH has nucleophilic character b) H has electrophilic character
c) OX has nucleophilic character d)X has nucleophilic character
7 Propene on reaction with diborane followed by reaction with alkaline H 2O2
produces….

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 QB MSc-I (Chemistry) Sem-I & II

a) Propan-2-O1 b) Propan - 1-Ol

c) Propanal d) Propenal
8 Cis-2-butene on Cis hydroxylation in presence of OsO 4 produces…
a) Threo 1,2-diol b) Meso- 1,2-diol
c) Trans 1,2-diol d) None
9 Markovnikov's addition of HBr is not applicable to…
(a) Propene (b) 1-butene
(c) 1-pentene (d) 2-butene
10 2-Methyl-2-butene reacts with HBr in the presence of peroxide to give….
(a) A primary alkyl bromide (b) A secondary alkyl bromide
(c) A tertiary alkyl bromide (d) A vicinal dibromide
11 Which of the following alkenes reacts with HBr in the presence of a peroxide to give
anti-Markovnikov's product?
(a) 1-Butene (b) 2,3-Dimethyl-2-butene
(c) 2-Butene (d) 3-Hexene
12 Which of the following on reaction with alkaline KMnO 4 produces cis 1,2-
cyclohexane diol..
a) Cyclohexene b) Cyclohexadiene
c) Cyclohexatriene d) Cyclohexane
13 Trans-2-butene on reaction with organic per acid produces…
a) Cis diol b) Trans diol
c) Epoxide d) Alkoxide
14 Molozonide breaks up into a..
a) Zwitter ion b) carbonyl compound
c) Carbonyl compound and zwitter ion d) carboxylic acid
15 2-methyl-2- butanol can be obtained by hydration of….
a) 2-methyl - 1 butene b) 2-methyl-2-butene
c) Both a and b d) 2-butene
16 Bromoethene on reaction with HBr gives..
a) 1.2-dibromo ethane b) 1, 1- dibromo ethane
c)1,2-dibromo ethane d) 1,1-dibromo ethene
17 When HX is added to alkene, hybridization of carbon changes from
a) SP3 to SP2 b) SP2 to SP3
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c) SP to SP d) SP to SP2
18 The correct order of reactivity of Halo acid for reaction with alkenes is…
a) HF> HC > HBr > HI b) HF < HCI< HBr< HI
c) HI< HF< HCl < HBr d) HBr < HCI< HF < HI
19 Alkenes undergo electrophilic addition reaction with hypochlorous acid to
produce…..
a) Alkyl chloride b) Chlorohydrin
c) Alkane d) Dichloro ethane
20 Ozonolysis of isobutylene produces
a) Propanone and ethanol b) propanone and methanol
c) Ethanal and propanone d) propionic acid and ethanoic acid
21 Predict the product

a) Ph-CH2-CH2-OH b) Ph-CH(OH)-CH3

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c) Ph-CH2-CH2-CH(OH)-CH3 d) Ph-CH2-CH2-OCH3
22 Unsaturated compounds undergo which of the following reactions easily?
a) Electrophilic substitution reactions b) Electrophilic addition reactions
c) Nucleophilie substitution reactions d) Nucleophilic addition reactions
23 The most suitable catalyst for the hydrogenation of 2-hexyne to cis-2-hexene is.
(a) Pd-BaSO4 (b) (PPh 3)3RhCl
(c) 10%-Pd-C (d) Raney Ni
24 3-Hexyne reacts with Na/liq. NH 3 to produce…
a) cis-3-hexene (b) trans-3-hexene
c) 3-hexylamine (d) 2-hexylamine
25 Reduction of 1-butyne with sodium in liquid ammonia gives predominantly…
(a) cis-2-butene (b) trans-2-butene
c) n-butane (d) no reaction

Answers-

1) b 2) b 3) a 4) d 5) d
6) a 7) b 8) b 9) d 10) b
11) a 12) a 13) c 14) c 15) c
16) b 17) b 18) b 19) b 20) b
21) a 22) b 23) a 24) b 25) c

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