CLS JEEAD-19-20 XI Che Target-5 Level-2 Chapter-12
CLS JEEAD-19-20 XI Che Target-5 Level-2 Chapter-12
CLS JEEAD-19-20 XI Che Target-5 Level-2 Chapter-12
Chapter 12
Organic Chemistry : Some Basic
Principles and Techniques
Solutions
SECTION - A
Objective Type Questions (One option is correct)
1. Which of the following reactions is incorrectly matched?
CH3 CH3
+ H3C CH3
H
(1) H3C C C H C C — (elimination reaction) + rearrangement
CH3 CH3
CH3 OH
CH3 CH3
–
OH
(2) CH3 C CH2I
(aq)
H3C C CH2 CH3 — nucleophilic substitution + rearrangement
CH3 OH
OH
H3PO4
(3)
+ H2O — Elimination
CH3 CH3
NaOH
(4) CH3 C CH2 CH2Cl (aq)
CH3 C CH2 CH2OH — nucleophilic substitution + rearrangement
H H
Sol. Answer (4)
CH3 CH3
NaOH
CH3 C CH2 CH2Cl CH3 C CH2CH3 (Nucleophilic substitution + rearrangement)
aq.
H OH
2. During Lassaigne’s test ‘S’ and ‘N’ present in an organic compound change into
(1) Na2SO4 and NaCN (2) Na2S and NaCN
(3) Na2S and NaCNO (4) NaCN and NaCNO
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Sol. Answer (2)
During Lassaigne's test 'S' and 'N' present in an organic compound change into Na2S and NaCN.
Na C N NaCN
2Na S Na2S
Steam distillation process is suitable for purification of aniline from aniline-water mixture.
4. Pick out the incorrect statement about the barrier of rotation about the indicated bond in the given compounds.
I II III IV
I II III IV
(1) II < I < IV < III (2) IV < III < I < II (3) II < I < III < IV (4) III < IV < II < I
–H
Least acidic
Lesser delocalization
of negative charge,
hence least stable
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30 Organic Chemistry : Some Basic Principles and Techniques Solutions of Assignment (Level-II)
N N
N N
N
N
H N N
H
I II III IV
(1) I > II > IV > III (2) III > IV > II > I (3) IV > III > I > II (4) II > I > III > IV
Sol. Answer (4)
Conjugate acids of I and II are stabilized by resonance.
7. The correct stability order of the following resonance structures is
OMe O—Me
Me Me
N N CH2
Me CH2 Me
(I) (II)
O—Me OMe
Me Me
N CH2 N CH2
Me Me
(IV) (III)
(1) I < III < IV < II (2) I < IV < III < II (3) I < IV < II < III (4) IV < I < II < III
Sol. Answer (3)
More number of covalent bonds more contributing structures.
8. Correct statements among the following is/are
D D D D
(1) and are identical compounds
D D D D
(2) and are structural isomers
D D
D D
(3) and are not identical compounds
D D
D D
(4) and are structural isomers
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Sol. Answer (2)
Me
Keq
Me
Me at axial Me at equatorial
position position
What is the percentage of axial conformer if the equilibrium constant for the given equilibrium is 18?
(1) 5 (2) 10 (3) 15 (4) 95
Sol. Answer (1)
[Equatorial conformer] 18
K
[Axial conformer] 1
[Equatorial conformer] 18
Percentage equatorial conformer 100 100 = 95%
[Equatorial] [Axial conformer] 18 1
(1) (2)
I II
(3) (4)
III IV
Sol. Answer (2)
Maximum delocalization of positive charge occur in II.
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32 Organic Chemistry : Some Basic Principles and Techniques Solutions of Assignment (Level-II)
12. For which of the following compound tautomerization reaction is very slow?
O—H O
(1) C C
F2C CH3 HF2C CH3
O—H O
(2) C C
H2C CH3 H3C CH3
O O
(3)
H
O O
(4)
O O
H
O
O O
S S
S O S S
O O
O O
I II III IV
O O O O
NH3 H—C CH3—S—OH
O—H HH
O
I II III IV
(1) II > I > III > IV (2) IV > II > I > III (3) III > IV > II > I (4) II > IV > I > III
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Solutions of Assignment (Level-II) Organic Chemistry : Some Basic Principles and Techniques 33
Sol. Answer (2)
IV > II > I > III
Decreasing acidic strength
CH—CH2 OH OH
O
O
OH OH
(1) (2) H (3) (4)
HO OH
Sol. Answer (1)
Except naphthalene all three compounds can trap free radicals due to presence of oxygen.
SECTION - B
Objective Type Questions (More than one options are correct)
1. Which of the following bicyclic compounds are isomers?
CH3
+ BuLi
(3) CH3—C—OH H (4)
CH3
Sol. Answer (1, 2)
O O O
h
Ph—C—O—O—C—Ph 2Ph—C—O
h
R—O—Cl R—O + Cl
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3. Species which will exhibit geometrical isomerism among the following is/are
T D
CH3
H
C C C N—OH
(1) (2) Br (3) (4) N2H2
H 3C
H Me
4. Which of the following molecular formula will exhibit functional isomerism as well as metamerism?
For molecular formula C4H11N only saturated amines are possible (1°, 2° & 3° amines are functional isomers)
Molecular formula C4H9Cl only represents saturated alkyl chloride. Therefore metamerism is not possible.
5. Out of the given isomeric hydrocarbons which will undergoes rearrangement reaction in acidic medium?
+H
(1)
Stable tertiary
carbocation
+H
(2)
Stable tertiary
carbocation
(No rearrangement
possible)
CH2
CH 3
(1) CH2 CH — CH2 (2) C (3) C (4)
CH 3
CH3
CH2
(1) CH3 — C — C — O (2) (3) — CH (4)
CH3 CH3
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Sol. Answer (1, 3, 4)
CH3 CH 3
+
CH3—C + CO
+
CH3—C—C = O
CH3 CH 3
+
CH—CH3 +
CH3
+ +
CH2
O O
O
(1) (2) (3) (4) O C O
CH2
(3) HC C H2 C CH CH3 CH2 (4)
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Me Me
(1) CH3 (2) CH2 (3) (4)
Me Me
Sol. Answer (1, 2, 4)
In CH3 and there is no hydrogen
+
In CH2 , stability is due to overlapping of p-orbital
Cl
Cl – CH = CH – Cl can show geometrical isomerism and CH 2 CH is its position isomer
Cl
(1) Metamerism (2) Functional isomerism (3) Chain isomerism (4) Position isomerism
14. Which of the following correctly represents the order of quality mentioned in bracket?
(1) sp – sp > sp2 – sp2 > sp3 – sp3 (bond energy) (2) sp – sp3 > sp – sp2 > sp – sp (polarity in bond)
(3) sp3 – s < sp2 – s < sp – s (% s character) (4) sp3 – sp3 > sp2 – sp2 > sp – sp (bond stability)
sp, sp2 & sp3 have 50%, 33% and 25% s-character.
N N
H NH2
(I) (II) (III)
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Solutions of Assignment (Level-II) Organic Chemistry : Some Basic Principles and Techniques 37
16. Which of the following correctly represent the acidic strength of given acids?
(1) Cl3CH > F3CH (2) CH3COOH > CH3CH2OH
OH OH
NO2
Sol. Answer (1, 2, 3, 4)
CCl3 is more stable than CF3– due to presence of d-orbital in CCl3 hence CHCl3 is more acidic than CFCl3.
17. Which of the following correctly represents the stability of reactive intermediate?
+
(1) CH3–CH2 < CH3OCH2 (2)
CH2 CH2
CH3
(3) > (4) CH3–CH2–C < CH3CH2
CH3
NO2 CH3
Sol. Answer (1, 2, 3)
CH3 —O— CH2 is a resonance stabilized carbocation.
18. The correct order of basic strength in aqueous medium is/are
(1) (C2H5)2NH > (C2H5)3N > C2H5–NH2
(2) (CH3)2NH > CH3–NH2 > (CH3)3N
(3) CH3 – NH – CH2 – CH3 > CH3 CH CH3 > CH3 – CH2 – CH2 – NH2
|
NH2
(4) C2H5 – NH2 > CH3 – NH2 > CH2 = CH – NH2
Sol. Answer (1, 2, 3, 4)
These orders are due to steric hindrance and different Kb value.
19. Keto-enol Tautomerism is observed in
(1) C6H5–CHO (2) C6H5–CO–CH3
O
H 2N H NH2
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H H
(1) C6H5CH = N – OH (2) (3) (CH3)2C = C(CH3)2 (4)
Me Me
Sol. Answer (1, 4)
Ph OH Ph
C N and C N
H H OH
Geometrical isomers
H H H Me
and
Me Me Me H
Geometrical isomers
O
CH—C—NH
3 2 N N CH3 — C N
sp2 sp
sp 2
sp2 H
23. Which of the following Lewis structures are valid resonating structures for the azide ion?
N
–
(1) N—
—N—N (2) N N N (3) N N N (4)
N N
N N N
Invalid resonating structure because of extension of octet around N.
N
N N Invalid structure because position N atom is changing as well as no. of -electrons are also
changing.
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24. In the given compound the hybridisation states of C atom is/are not
SECTION - C
Linked Comprehension Type Questions
Comprehension-I
Tautomerism, strictly defined could be used to describe the reversible interconversion of isomers. Interconversion
of isomers is due to mobility of an atom or a group.
R R
R—HC—C O R—CH C—O
H H
In the above examples the composition of the equilibrium mixture is of course, governed by the relative
thermodynamic stability of the two forms under the particular conditions being studied.
1. In which of the following tautomeric equilibrium concentration of right hand product is more than left hand
product?
O O
(1) CH3—N CH2—N
O O—H
H
O O
CH3 O
(2)
H3C O H2C OH
O OH
(3)
O
O OH O
(4) C
EtO OEt EtO OEt
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O O
H
H
More stable
2. In which of the following solvent percentage enol content is maximum for 2,4-pentanedione?
(1) CH3CN (2) H2O (3) n-Hexane (4) Ethanol
Sol. Answer (3)
In non-polar solvent enol content would be maximum.
Comprehension-II
Names of organic compounds are under the latest guide line of IUPAC. IUPAC means international union of
pure and applied chemistry. The main rules are longest chain rule, lowest number rule etc. We have to include
the rules for naming the substituents, multiple bonds and even functional groups.
1. Write the IUPAC name of the following compound
CN
CN
(1) 3,3-Diethenyl pentane1,5-dinitrile (2) 3,ethenyl,3-ethyl pentane 1,5-dinitrile
(3) 3,3-diethenyl pentane 1,5-dicyanide (4) None of these
Sol. Answer (1)
(4)
(5)
CN
(3)
(2)
CN
(1)
OH
2. , IUPAC name is
OH
(1) 3,3-diethenyl pentane 1,5-diol (2) 2,2-diethenyl propane 1,3-diol
(3) 2, 3-diethenyl propane 1,3-diol (4) 3,3-diethenyl propane 1,3-dialcohol
Sol. Answer (2)
(3)
(2) OH
(1)
OH
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3. Write IUPAC name of
3
4 2
1
5
6 4
3
1 2
OH OH OH OH
CH3
(1) (2) (3) (4)
CH3
CH3
Sol. Answer (1)
Alkyl group (electron donor) decreases acidic strength of phenol.
2. Which of the following is having most acidic -Hydrogen?
O
(1) CH3—NO2 (2) CH2 NO2 (3) NO2 CH NO2 (4)
NO2 NO2
O
Sol. Answer (3) H
NO2
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42 Organic Chemistry : Some Basic Principles and Techniques Solutions of Assignment (Level-II)
H H H H
H C H H C H H C H H C H
Hydrocarbon (1) is least stable, as it is not stabilized by resonance, and has lesser number of hyper
conjugative structures.
SECTION - D
Matrix-Match Type Questions
Column-I Column-II
Carbonyl compounds, unsaturated alcohols and ethers are possible. This can also exhibit geometrical
isomerism.
C4H11N can form 1°, 2° & 3° amines which are functional isomer.
Column-I Column-II
(Estimation) (Method)
Factual based
Column-I Column-II
(Estimation) (Percentage)
(C) 0.37 gm of a given compound gave 0.631 gm AgBr (r) Equivalent mass of acid is 122
(D) 0.122 gm of an organic acid required (s) 72.6% Br
N
10 cm3 NaOH for neutralisation
10
12 Mass of CO2
(A) Percentage of C = 44 Mass of organic compound 100
12 1.10
100 66.6%
44 0.45
2 Mass of H2 O
Percentage of H = 18 Mass of compound 100
2 0.3
100 7.4%
18 0.45
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18
(B) Percentage of C = 100 66.66%
27
2
Percentage of H = 100 7.40%
27
7
Percentage of N = 100 26%
27
80 Mass of AgBr
(C) Percentage of Br = 188 Mass of compound 100
80 0.631
100 72.6
188 0.37
N
(D) 10 cm3 of alkali required acid = 0.122 g
10
0.122
1000 cm3 of 1 N alkali required acid = 1000 10
10
= 122 g
But 1000 cm3 of 1 N alkali contain 1 gm equivalent of the alkali which must react with 1 gm equivalent
of acid.
Equivalent weight of acid = 122
4. Match the carbocation in column-I with the effect which is major, stabilizing factor for it in column-II.
Column-I Column-II
(A) Carbocation (p) Nucleophile
(B) Carbanion (q) Electrophile
(C) Free radical (r) Stabilized by +I effect
(D) Carbene (s) Stabilized by resonance
Sol. Answer A(q, r, s), B(p, s), C(r, s), D(p, q, s)
Carbocation is electrophile and stabilised by +I effect resonance and hyperconjugation.
Carbanion is nucleophiles and stabilized by resonance and –I effect.
Free radical is electrophile and stabilised by resonance and hyperconjugation.
Carbene can act as electrophile and nucleophile both.
5. Match the carbocation in column-I with the effect which is major, stabilizing factor for it in column-II
Column-I Column-II
+
CH3 CH has 6 –H for hyperconjugation and 2 methyl groups for + I effect.
CH3
+
is aromatic resonance stabilised cation
CH3 –O– CH2 is resonance stabilised because it can form CH3 – O CH2 .
SECTION - E
Assertion-Reason Type Questions
1. STATEMENT-1 : In naphthalene all C—C bonds are equal.
Naphthalene
and
STATEMENT-2 : Like benzene naphthalene is also aromatic.
Sol. Answer (4)
HO O OH
O
Squaric acid
Phenol
and
Br
5. STATEMENT-1 : When is treated with excess of Ag+ ion. One mole of the compound reacts
Br
Br
Br
(X)
with four moles of Ag+.
and
STATEMENT-2 : Ag+ is a Lewis acid hence it reacts with Br– ion on which is a Lewis base.
6. STATEMENT-1 : Bridge head carbocation is less stable than Bridge head carbanion.
and
7. STATEMENT-1 : Aldehydes and ketones having same molecular formulae are structural isomers.
and
and
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9. STATEMENT-1 : Cyclopentanone exhibits keto-enol tautomerism.
and
STATEMENT-2 : Cyclopentanone has two hydrogen atoms attached to the carbon atom adjacent to carbonyl
group.
Sol. Answer (1)
O OH
Tautomers
10. STATEMENT-1 : CH3 CH2 CH2 is less stable than CH3 – N – CH2
|
H
and
STATEMENT-2 : Carbocation with adjacent hetero-atom like N, O are less stable.
Sol. Answer (3)
If ‘N’ or ‘O’ are attached to carbocation. These groups participate in the delocalization of +ve charge.
11. STATEMENT-1 : Cyclopropane is more stable than cyclobutane.
and
STATEMENT-2 : Angle strain in cyclopropane is higher than cyclobutane.
Sol. Answer (4)
1
Angle strain of cyclic compound.
stability
O
||
12. STATEMENT-1 : Keto form is less stable than enol form.
O
||
and
STATEMENT-2 : Enol form is stabilized by aromaticity.
Sol. Answer (1)
O OH
O
OH
13. STATEMENT-1 : Aniline undergoes Friedel-Craft alkylation more readily than Toluene.
and
STATEMENT-2 : Aniline undergoes fast electrophilic substitution than Toluene.
Sol. Answer (4)
Aniline does not follow Friedel-Craft reaction.
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48 Organic Chemistry : Some Basic Principles and Techniques Solutions of Assignment (Level-II)
SECTION - F
Integer Answer Type Questions
1. One mole of a compound with molecular formula C30H43N absorbs 8 moles of H2 gas under catalytic
hydrogenation. Then what is the ratio of number of bonds to the number of rings in the compound?
43 1
Degrees of unsaturation in the compound = 31 = 31 – 21 = 10
2
Out of which 8 bonds are present.
bond 8
Hence 4
ring 2
2.
How many intermediates are possible (excluding stereoisomer) when above mentioned molecule is attacked
by 1 equivalent H+?
F F F F
–
NH3, NH4, CH3 and OH are not electrophiles, infact they are nucleophiles .
5. How many bicyclic isomers are possible for the molecular formula C6H12O?
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Solutions of Assignment (Level-II) Organic Chemistry : Some Basic Principles and Techniques 49
6. How many of the given species will evolve CO2 with NaHCO3?
OH OH OH
HO O O CH CH2
O2N NO2 O OH OH
, , , , H
,
O
HO HO OH
NO2
(i) (ii) (iii) (iv) (v)
O O OH OH
NO2 NO2
, , , ,
O
O NO2
(vi) (vii) (viii) (ix)
y
x+ 7.5
2
x
x 7.5
4
x = 6, y = 6
10. Total number of ketones (including stereoisomer) with molecular formula C6H12O is
Sol. Answer (7)
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