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CET OBJECTIVE QUESTIONCET OBJECTIVE QUESTION ON
1. CONCEPTS IN ORGANIC CHEMISTRY2. SYNTHETIC ORGANIC CHEMISTRY3. ISOMERISM – II4. HYDROCARBONS – II5. HALOALKANES
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1.The inductive effecta. Implies the atoms ability to cause bond
polarization b. Increases with increase in distancec. Implies the transfer of lone pair of
electrons from more electronegative atom to the lesser electronegative atom in a molecule
d. Implies the transfer of lone pair of electrons from lesser electronegative
Vikasana - CET 2012atom to more electronegative atom in a molecule
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2. The oxygen atom in phenol
a. Exhibits only inductive effect
b E hibi l ffb. Exhibits only resonance effect
c Has more dominating resonancec. Has more dominating resonance
effect then inductive effectd. Has more dominating inductive
effect than resonance effectVikasana - CET 2012
effect than resonance effect
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3. The activating effect of –OCH3 group attached to the benzene ring can be explained in terms of
a. +R effect
b. –R effect
E ff tc. + E effect
d – I effectVikasana - CET 2012
d. – I effect
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4. Orbital interaction between sigma bonds of a substituent group and a neighboring π– orbital is known as
a. Sterric effect
b. Inductive effect
El t i ff tc. Electromeric effect
d Hyperconjugation effectVikasana - CET 2012
d. Hyperconjugation effect
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5. Amongst the following the most basic compound iscompound is a. Aniline b. Benzyl amine c p – nitroanilinec. p – nitroanilined. AcetanilideI B l i h l i fIn Benzylamine, the lone pair ofElectrons on N atom of amino group
dil il bl f D tiVikasana - CET 2012
are readily available for Donation
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6. The group which exerts both +R and –R effect is a. –NO2 b. –NHRc – NOc. – NO d. –OCH3
In –NO ( Nitroso group) , release of lonepair of electrons of nitrogen away frompair of electrons of nitrogen away fromsubstituent, is +R effect, While shift of π( pi) electron pair of N=O bond is due to
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( pi) electron pair of N=O bond is due to–R effect.
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7. For an optically active compound, which of the following requirement is necessary?
a. A double bond
b. Presence of one chiral carbon
c. Presence of plane of symmetry
d none of theseVikasana - CET 2012
d. none of these
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8 A compound with molecular formula C H h ti l i i thC7H16 shows optical isomerism, the compound will bea. 2, 3-dimethylpentaneb. 2, 2-dimethylpentane, y pc. 2-methylhexaned None of thesed. None of these
The molecule has a asymmetric carbon at C S it h ti l ti it
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C3. So it show optical activity
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9. In the reaction CH3CHO + HCN → CH3CH(OH)CNC 3C O C C 3C (O )Ca chiral centre is produced. Thus product would beproduct would bea. Meso compound b R i i tb. Racemic mixture c. Laevorotatory d. Dextrorotatory
The products containing one chiral carbon are always Racemic.
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y
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10. Meso-Tartaric acid is optically inactive due to the presence ofdue to the presence ofa. Molecular asymmetryb P f hi litb. Presence of chirality c. Internal compensationd. External compensation
Cancellation of optical activity due topresence of plane of symmetry
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presence of plane of symmetry
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11. When Cyclohexane is poured in water, it floats becausefloats because
a. Cyclohexane is in boat formy
b. Cyclohexane is in chair form
c. Cyclohexane is in crown from
d. Cyclohexane is less dense than water
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12. Alcoholic potash is used in organic chemistry to bring aboutchemistry to bring abouta. Dehydrogenation b. Hydrationc. Dehydrohalogenation d. Hydrohalogenation
In Alcoholic KOH OH- acts as a base andIn Alcoholic KOH, OH acts as a base andabstracts a proton and results indehydrohalogenation
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dehydrohalogenation
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13. Isopropyl chloride is prepared in the laboratory by the action of drylaboratory by the action of dry hydrogen chloride on isopropyl alcohol in the presence of anhydrous zincin the presence of anhydrous zinc chloride. This reaction is known asa Dehydrationa. Dehydration b. Dehydrohalogenation c. Hydrolysisd. oxidation
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d. oxidation
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14. Alkyl halides on treatment with aqueous KOH giveaqueous KOH givea. Alkanes b A idb. Acids c. Alkenes d. Alcohols
In aqueous KOH, OH- acts as aIn aqueous KOH, OH acts as anucleophile which attacks the positivecenter giving substitution product
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center giving substitution product
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15. The reactivity of alkyl halides follows the following orderfollows the following ordera) C2H5Cl > C2H5Br > C2H5Ib) C H I > C H B > C H Clb) C2H5I > C2H5Br > C2H5Clc) C2H5Br > C2H5I > C2H5Cld) C2H5Cl > C2H5I > C2H5Br
The alkylhalide having weaker C-X bond has greater reactivity
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has greater reactivity
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16. Which one of the following is an Aralkyl halideAralkyl halide
a. Chlorobenzene
b. Bromobenzene
c. Benzyl chloride
d. Ethyl bromide
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17. A gas formed by the action of alc. KOH on ethyliodide decolourises alkalineon ethyliodide, decolourises alkaline KMnO4. the gas is
a. CH4
b C Hb. C2H6
c C2H4c. C2H4
d. C2H2
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2 2
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18. SN1 reaction is favored by
a. Polar solvents
b N l hil b ild ib. Nucleophile can be mild in nature
c Low concentration for nucleophilec. Low concentration for nucleophile
d. All the three
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19. Complete inversion of configuration takes place intakes place in
a. SN2N
b. SN1
c. Both
d. None
Vikasana - CET 2012Walden Inversion takes place
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20. The order of reactivity of alkylhalide through S 2 mechanism isthrough SN2 mechanism is
a. 10>20 > 30
b. 10>20 < 30
c. 10<20 > 30
d. 10<20 < 30
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21. Benzene reacts with acetyl chloride in presence of AlCl to givepresence of AlCl3 to give
a. Toluene
b. Xylene
c. Acetophenone
d. Benzophenone
Vikasana - CET 2012This is Friedel- crafts acylation
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22. In SN2 reaction at chiral carbon of a compound always givescompound always givesa. An Enantiomer of the substrateb. A product with opposite optical
rotationc. A mixture of Diastereomersd. A single stereoisomerd. A single stereoisomer
Inversion of configuration takes place. Single stereoisomer is produced which
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Single stereoisomer is produced which need not be optically active
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23. SN1 reaction of alkyl halides leads to
a. Retention of configuration
b. Racemisation
c Inversion of configurationc. Inversion of configuration
d Noned. None Because both the isomers are formed.This
l d t ll ti i ti l t tiVikasana - CET 2012
leads to cancellation in optical rotation
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24. The process of separation of Racemic modification into d and I isomers is called
a. Resolution
b. Dehydration
R l tic. Revolution
d HydrationVikasana - CET 2012
d. Hydration
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25. Propene is reacted with HBr in the presence of peroxide the product ispresence of peroxide, the product is
a. 2-Bromopropane
b. 1-Bromopropane
c. 3- Bromopropane
d. None of theseThe reaction is governed by Anti-
Vikasana - CET 2012
The reaction is governed by Anti-Markwonikoff’s rule
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26. Which of the following alkylhalides is used as methylating agent?used as methylating agent?
a. C2H5Cl
b. C2H5Br
c. C2H5I
d. CH3I
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27. 1-Chlorobutane when treated with alcoholic potash givesalcoholic potash gives
a. 1-Butene
b. 2-Butanol
c. 2-Butene
d. 2-Butanol
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28. The product obtained on treatment ofethyl chloride with potassium cyanideethyl chloride with potassium cyanidewas reduced by sodium and alcohol togivegivea. Propyl amineb th l ib. ethyl aminec. acetic acidd. butyl amine
C H Cl + KCNNa/C2H5OH
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C2H5-Cl + KCN C2H5CN 2 5CH3CH2CH2NH2
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29. Butanenitrile may be prepared by heatingg
a. Propyl alcohol with KCN
b. Butyl chloride with KCN
c. Propyl chloride with KCN
d B t l l h l ith KCNd. Butyl alcohol with KCN
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30. Most reactive halide towards SN1 reaction isreaction is
a. n-Butyl chloride
b. sec-Butyl chloride
c. tert-Butyl chloride
d. Ethyl chloride
More stable carbocationVikasana - CET 2012
More stable carbocation
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31. If methyl bromide and ethyl bromide are mixed in equal proportions and theare mixed in equal proportions and the mixture is treated with sodium, the number of possible alkanes formed isnumber of possible alkanes formed is a. 1
b. 2
3c. 3
d 4Vikasana - CET 2012
d. 4
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32. Carbon―Carbon bond length in benzene isbenzene is
a. 134 pm
b. 154 pm
c. 139 pm
d. 143 pm
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33. Heating a mixture of sodium benzoate or benzoic acid and soda lime givesor benzoic acid and soda lime gives
a. Toluene
b. Phenol
c. Benzene
d. Sodium chloride
Soda lime is a decarboxylating agentVikasana - CET 2012
Soda lime is a decarboxylating agent.
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34. Catalytic hydrogenation of benzene givesg
a. Benzoic acid
b. Toluene
c. Cyclohexane
d X ld. Xylene
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35. Benzene is converted into toluene by
fa. Friedel – crafts reaction
b Grignard reactionb. Grignard reaction
c. Wurtz reaction
d. Perkin reaction
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36. Nitration of toluene using fuming sulphuric acid and nitric acids givesulphuric acid and nitric acids give
a. Trinitro toluene
b. o – nitro toluene
c. m – nitrobenzene
d. p- nitro phenol
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37. Which of the following theories can explain the stability of Cyclohexaneexplain the stability of Cyclohexane and its higher members?
B i ha.. Bayer strain theory
b Sachse Mohr’s theoryb. Sachse-Mohr s theory
c. Arrhenius theory y
d. None of the above
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38. Which of the following deactivates benzene substitution?benzene substitution?
a. –NHR
b. –OH
c. –OR
d. –COOR
COOR is a electron withdrawing groupVikasana - CET 2012
–COOR is a electron withdrawing group
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39. In nitration Conc. H2SO4 acts as
Sa. Sulphonating agent
b Helps in producing NO +b. Helps in producing NO2
c. Produces SO33
d. Dehydrating agent
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40. -COOH group present on the benzene ring directs the incoming group toring directs the incoming group to
a. o-position
b. p-position
c. m-position
d. o and p
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41. Isopropyl chloride undergoes hydrolysis byhydrolysis bya. SN1 mechanismb. SN2 mechanismc. SN1 mechanism and SN2 mechanismN N
d. None
20 halides may undergo SN1 as well SN2
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42. The ratio of л to σ bonds in benzene isis
a. 1:2
b. 1:3
c. 1:4
d. 4:1
Vikasana - CET 2012There are 3 л and 12 σ bonds in benzene
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43. Which of the following is the most reactive Cycloalkane?reactive Cycloalkane?
a. Cyclopropane
b. Cyclobutane
c. Cyclopentane
d. CyclohexaneBecause it is most strained Cycloalkane
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Because it is most strained Cycloalkane
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44. Select the true statement from the followingga. Because of unsaturation benzene undergoes addition reactionundergoes addition reaction.b. There are two types of C–C bonds in benzene moleculebenzene molecule.c. There is a cyclic delocalization of л l t i belectrons in benzene.
d. Monosubstitution of benzene
Vikasana - CET 2012molecule gives 3 isomeric substances.
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45. Which of the following can be used as a catalyst in Friedel Crafts reaction?a catalyst in Friedel- Crafts reaction?a. AlCl3b. BF3
c. Bothd. None
Any Lewis acid can be used as a catalystAny Lewis acid can be used as a catalyst in Friedel –Crafts reaction
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46. An enantiometrically pure acid is treated with a Racemic mixture of an alcohol having one chiral carbon. The ester formed isa. Optically active mixtureb Pure enantiomerb. Pure enantiomerc. Racemic mixtured M dd. Meso compound
Optically active compound when treated
Vikasana - CET 2012with Racemic mixture give optically active isomers
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47. Cis-2-butene and trans-2-butene can be distinguished bybe distinguished bya. Their Physical propertiesb. Their reduction propertiesc. Products on Ozonolysisd. Their addition product with Br2
Addition of Br2 to alkene is a trans addition Hence products of two isomers
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addition . Hence products of two isomers are different
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48. The bond angle in Chair and boat form of Cyclohexane isform of Cyclohexane is
a. 1200
b. 1090 28|
c. 600
d. 1800
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49. A compound that undergoes b i ti il ibromination more easily is
a. Benzoic acida. Benzoic acid
b. Toluene
c. Benzene
d. Phenol
Vikasana - CET 2012+R effect is predominant in Phenol
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50. Benzene can be obtained by heating either benzoic acid with ‘X’ or phenoleither benzoic acid with X or phenol with ‘Y’. X and Y are respectivelya Zinc dust and NaOHa. Zinc dust and NaOHb. Soda lime and copper c. Zinc dust and soda lime d. Soda lime and Zinc dust
C 6 H 5 C O O N a + N a O H C 6 H 6 + N a 2 C O 3
C H O H + Z n C H + Z n O
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C 6 H 5 O H + Z n C 6 H 6 + Z n O
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