Test – 44

CHEMISTRY
Organic Chemistry - Some basic principles &Techniques

Q.1 The incorrect match is (a) 4-methoxy-1-methylchlorobenzene

(a) CnH2n – 2 – Alkyne (b) 2-chloro-1-methoxy-4-methylbenzene
(b) CnH2n – Alkene (c) 1-methoxy-2-chloro-4-methylbenzene
(c) CnH2n + 2 – Bicycloalkane (d) 4-methyl-2-chloroanisole
(d) CnH2n – Alkadiene CH 3 – CH 2 – CH 2 – CH – CH 3 and
–2 Q.8
Q.2 IUPAC name for the compound having |
formula C(CH3)4 is OH

(a) Tetramethylmethane CH 3 – CH 2 – CH – CH 2 – CH – CH 3 are

|
(b) 1, 1, 1, 1-Tetramethylmethane OH
(c) 2, 2-Dimethylpropane (a) Functional isomers (b) Position isomers
(d) 2, 2-Dimethylisopropane (c) Chain isomers (d) These are not isomers
Q.3 IUPAC name of the compound Q.9 The most stable alkene is
(a) CH2 = CH – CH2 – CH3
(b) CH 2  C  CH  CH 2
(a) Cyclopentylethyne (b) Ethynylcyclopentane |
CH3
(c) Cyclopentylacetylene (d) Ethynylpentane
Q.4 The IUPAC name of CH3–CHBr–CH2OH is (c) CH2 = CH – CH = CH2

(a) 3-Hydroxy 2-bromopropane (d) CH3 – CH = CH – CH3

(b) 2-Bromopropan-1-ol Q.10 The nucleophile is not
(c) 2-Bromo 3-propanol (a) Lewis base (b) Lewis acid

(d) 3-Hydroxy isopropyl bromide
(c) H 2 O (d) Carbanion
Q.5 The IUPAC name of the following compound 

CH 3 – C – C – CH 3  :
O
|| || is  |
O O Q.11 In C H 2 – HC = C – H and
(I)
(a) Butandione (b) 2,3–Butandiketone
 :

(c) Butane–2,3–dione (d) None of these O

 |
Q.6 The number of tertiary carbon atoms in the CH 2 – CH = CH – C – H most stable is
(II)
following structure is
(a) (I)
CH 3 CH 3
| | (b) (II)
CH 3 – C – CH 2 – CH – CH 3
| (c) Sometimes (I) and sometimes (II)
CH 3 (d) Both are equal stable
(a) Four (b) Three
Q.12 The correct statement for -elimination is
(c) Two (d) One
(a) It forms cyclic compounds
(b) It forms carbene or substituted carbene
Q.7 The IUPAC name of ; is (c) Two atoms are removed from  and  positions
(d) In CHCl3;  elimination is not possible

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Q.13 Which of the following represents the correct (a) Both statements are correct
order of stability of the given carbocations? (b) Statement I is correct but statement II is
incorrect
(c) Statement I is incorrect but statement II is
correct
(d) Both statements are incorrect
(a) III > I > II (b) I > III > II Q.19 The function of boiling the sodium extract
with concentrated nitric acid before testing
(c) III > II > I (d) II > III > I
halogens is
Q.14 The most stable carbanion is
(a) To make solution clear
 
(a) CH 3  CH 2 (b) CH 2  CH (b) To destroy CN– and S2– ions

(c) To make the solution acidic

(c) CH  C (d) (CH 3 ) 2 CH (d) To disproportionate CN– and S–2
Q.15 The correct order of stability of Q.20 If 0.2 g of an organic compound on complete
    combustion produces 0.18 g of water then
CH 3 , CH 3CH 2 , (CH 3 )2 CH, (CH 3 )3 C; is % of hydrogen in it is
(I) (II) (III) (IV) (a) 5 (b) 10
(a) (IV) > (III) > (II) > (I) (c) 1 (d) 20
(b) (I) > (II) > (III) > (IV)
(c) (II) > (I) > (III) > (IV) Q.21
(d) (IV) > (II) > (III) > (I)
Q.16 Statement I : General formula of alkene = CnH2n Above two molecules are
Statement II : Resonance present in buta-1, 3- (a) Chain isomers (b) Position isomers
diene. (c) Metamers (d) All of these
(a) Both statements are correct Q.22 Aromatic enol is not possible in
(b) Statement I is correct but statement II is
incorrect
(c) Statement I is incorrect but statement II is
(a) (b)
correct
(d) Both statements are incorrect
Q.17 Statement I : NH2 is strong +R effect than –OH.
Statement II : Electronegetivity of nitrogen is
less than oxygen.
(a) Both statements are correct (c) (d)
(b) Statement I is correct but statement II is
incorrect
(c) Statement I is incorrect but statement II is
correct Q.23 The correct order of +I effect is
(d) Both statements are incorrect (a) COO  O   NH  CH 2

(b) CH 2  O  COO  C(CH3 )3

Q.18 Statement I : is a aeromatic compound.
(c) C(CH3 )3  O  COO   NH
Statement II : Aeromatic compound has (4n + 2) 
electrons. (d) O  COO  C(CH3 )3   NH

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Q.24 The stability of alkyl free radicals is due to
(a) Hyperconjugation (b) + I effect
(c)
(c) – I effect (d) Both (a) & (b)
Q.25 In the given compound

(d)

Q.28 The least reactive alkene towards dil. HCl is

The correct order of reactivity of H atoms
towards free radical substitution is
(a) 2 > 4 > 6 > 5 > 3 > 1 (a) (b) CH 3  CH  CH 2
(b) 2 > 4 > 5 > 6 > 1 > 3
(c) 1 > 4 > 2 > 5 > 6 > 3
(d) 3 > 1 > 5 > 6 > 4 > 2 (c) (d) CH 2  CH 2
Q.26 Which of the following is the correct order
of reactivity of chlorides for given
compounds? Q.29 Which of the following should be a sp 3
hybridised free radical?


(a) (b) CF3

(a) I > II > III > IV > V (b) I > III > II > IV > V (c) (d) Both (b) & (c)
(c) III > I > IV > V > II (d) I > III > IV > V > II
Q.27 In the given reaction Q.30 The charge on given atom cannot be dispersed
on other atom in
 
(a) NH2  CH  CH3 (b)

(c) (d) All of these

Q.31 The correct order of stability of given

A and B are respectively carbocations is

(a)

(a) I > IV > III > II

(b) I > IV > II > III
(b) (c) IV > I > III > II
(d) IV > I > II > III

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Q.32 The correct order of stability of given Q.36 Which of the following carbocations is expected
carbocations is to be most stable?
  
NO 2  CH 2  CH 2 NH 2  CH 2  CH 2 CH3  O  CH 2
(I) (II) (III)
HO  CH 2 NH 2  CH 2 NO 2  CH 2
(IV) (V) (VI)
 (a) (b)
CH 3O  CH 2  CH 2
(VII)
(a) VII > III > II > IV > V > I > VI
(b) V > III > IV > II > VI > I > VII
(c) V > IV > III > II > VII > I > VI
(d) VI > I > VII > III > II > V > IV
(c) (d)
+
H
Q.33  Intermediate (Major)

The most stable carbocation is Q.37 Which of the following is correct with respect
to – I effect of the substituents?
(R = alkyl)
(a) (b)
(a) – NH2 < – OR < – F
(b) – NH2 > – OR > – F
(c) – NR2 > – OR > – F
(c) (d)
(d) None of these
Q.34 In which of the following rearranged 3° Q.38 The correct statement regarding electrophile is
carbocation will not be formed? (a) Electrophile is a negatively charged species
and can form a bond by accepting a pair of
electrons from a nucleophile
(a) (b) (b) Electrophile is a negatively charged species
and can form a bond by accepting a pair of
electrons from another electrophile
(c) Electrophiles are generally neutral species
(c) (d) Both (a) & (c) and can form a bond by accepting a pair of
electrons from a nucleophile
Q.35 The most stable carbocation is (d) Electrophile can be either neutral or positively
charged species and can form a bond by
accepting a pair of electrons from a
nucleophile
Q.39 Statement I : Aniline is more acidic than
(a) (b) nitrobenzene.
Statement II : Anti-aeromatic compounds are
least stable than non-aeromatic compound.
(a) Both statements are correct
(b) Statement I is correct but statement II is
(c) (d) incorrect
(c) Statement I is incorrect but statement II is
correct
(d) Both statements are incorrect
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Q.40 The IUPAC name of the compound Q.44 Which among the given molecules can
exhibit tautomerism?

is _______.

(a) 3-keto-2-methylhex-4-enal
(b) 5-formylhex-2-en-3-one (a) III only (b) Both I and III
(c) 5-methyl-4-oxohex-2-en-5-al (c) Both I and II (d) Both II and III
(d) 3-keto-2-methylhex-5-enal Q.45 For the following reactions :
Q.41 In which of the following molecules, all atoms (a) CH 3CH 2CH 2Br + KOH  CH 3CH =
are coplanar? CH2 + KBr + H2O

(b)

(a) (b)
(c)

Which of the following statements is correct?

(c) (d) (a) (a) is substitution, (b) and (c) are addition reactions
(b) (a) and (b) are elimination reactions and (c)
is addition reaction
Q.42 In pyrrole the electron density is (c) (a) is elimination, (b) is substitution and (c) is
addition reaction
(d) (a) is elimination, (b) and (c) are substitution
maximum on reactions
(a) 2 and 3 Q.46 The pair of electron in the given carbanion,
(b) 3 and 4 CH 3C  C, is present in which of the following
(c) 2 and 4 orbitals?
(d) 2 and 5 (a) sp (b) 2p
3
Q.43 The correct corresponding order of names (c) sp (d) sp2
of four aldoses with configuration given below Q.47 The correct statement regarding a carbonyl
compound with a hydrogen atom on its alpha-
carbon, is
(a) A carbonyl compound with a hydrogen atom
on its alpha-carbon rapidly equilibrates with
its corresponding enol and this process is
known as keto-enol tautomerism
(b) A carbonyl compound with a hydrogen atom
on its alpha-carbon never equilibrates with
its corresponding enol
respectively, is (c) A carbonyl compound with a hydrogen atom
on its alpha-carbon rapidly equilibrates with
(a) L-erythrose, L-threose, L-erythrose, D-threose its corresponding enol and this process is
(b) D-threose, D-erythrose, L-threose, L-erythrose known as aldehyde-ketone equilibration
(c) L-erythrose, L-threose, D-erythrose, D-threose (d) A carbonyl compound with a hydrogen atom
(d) D-erythrose, D-threose, L-erythrose, L-threose on its alpha-carbon rapidly equilibrates with
its corresponding enol and this process is
known as carbonylation

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Q.48 2,3-Dimethyl-2-butene can be prepared by Q.50 Statement I : The IUPAC name of CH2=CH–C=CH
heating which of the following compounds is but-3-en-1-yne.
with a strong acid? Statement II : The priority of triple bond is more
(a) (CH3)2C = CH – CH2 – CH3 than double bond.
(b) (CH3)2CH – CH2 – CH = CH2 (a) Both statements are correct

(c) (CH 3 )2 CH  CH  CH  CH 2 (b) Statement I is correct & II is incorrect

| (c) Statement I is incorrect & II is correct
CH 3
(d) Both statements are incorrect
(d) (CH3)3C – CH = CH2
Q.49 Statement I : Addition of HCN in alkene is a
type of electrophilic substitution reaction.
Statement II : In first step, H3O+ attacks on
double bond.
(a) Both statements are correct
(b) Statement I is correct & II is incorrect
(c) Statement I is incorrect & II is correct
(d) Both statements are incorrect