CLS JEEAD-19-20 XI Che Target-5 Level-2 Chapter-12

Level-II
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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Solutions of Assignment (Level-II) Organic Chemistry : Some Basic Principles and Techniques 29
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
3. Which process is suitable for purification of aniline?
(1) Simple distillation (2) Steam distillation
(3) Fractional distillation (4) Fractional crystallisation
Sol. Answer (2)
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
(1) I and IV will have nearly same barrier of rotation
(2) II and III will have nearly same barrier of rotation
(3) At room temperature I will have frozen rotation
(4) III will have relatively higher barrier of rotation as compared to IV
Sol. Answer (4)
In II and III charge separated structures are more contributing.
5. Arrange the given species in the increasing acidic strength :
I II III IV
(1) II < I < IV < III (2) IV < III < I < II (3) II < I < III < IV (4) III < IV < II < I
Sol. Answer (3)
Stronger acids have more stable conjugate base.
–H
Least acidic
Lesser delocalization
of negative charge,
hence least stable
30 Organic Chemistry : Some Basic Principles and Techniques Solutions of Assignment (Level-II)
6. Order of basicity of the following species is
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
Sol. Answer (2)
is anti-aromatic while is aromatic.
9. Species in which all C—C bonds are equal is
(1) (2) (3) (4)
Sol. Answer (2)

(1) is anti-aromatic while (3) and (4) are non-aromatic. Therefore in these molecules less effective -
electron delocalization will occur and hence all C—C bonds will not be equal.
10. Consider the following equilibrium between two conformers of methyl cyclohexane
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
Percentage axial conformer = 5%

11. Most stable carbocation among the following is
(1) (2)
I II
(3) (4)
III IV
Sol. Answer (2)
Maximum delocalization of positive charge occur in 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
Sol. Answer (1)

In case of highly fluorinated enols the enol form is less stable than keto form. Yet enol form can be kept at
room temperature for long periods of time because the tautomerization reaction is very slow.
13. Aromatic species among the following is
(1) (2) (3) B—R (4) All of these
Sol. Answer (3)

Planar and contain 6 e–.
14. Most stable and least stable species respectively among the following are
O
O O
S S
S O S S
O O
O O
I II III IV
(1) II and I (2) IV and II (3) III and II (4) II and IV

Sol. Answer (4)
Maximum delocalization of negative charge is taking place in II. Electronegativity of S is less than oxygen.
15. Compare acidic strength of
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
Sol. Answer (2)
IV > II > I > III
Decreasing acidic strength
pKa of these acids are

Acid pKa
I 5
II 3.5
III 10
IV 1
16. Which of the following species is not used as antioxidant?
(Note : Antioxidants have capability to trap free radicals)
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?
(1) (2) (3) (4)
Sol. Answer (1, 2, 3, 4)

All of them have same molecular formula hence, they are isomers.
2. Which of the following will involve homolysis of a bond?
O O
h
(1) Ph—C—O—O—C—Ph h (2) RO — Cl 
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
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
Sol. Answer (1, 3, 4)
4. Which of the following molecular formula will exhibit functional isomerism as well as metamerism?
(1) C4H10O (2) C4H11N (3) C4H8O (4) C4H9Cl
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?
(1) (2) (3) (4)
Sol. Answer (2, 3)
+H
(1)
Stable tertiary
carbocation
+H
(2)
Stable tertiary
carbocation
(No rearrangement
possible)
6. Which of the following carbocation is stabilised by resonance?

CH2
 
CH 3 
(1) CH2  CH — CH2 (2) C (3) C (4)
CH 3
Sol. Answer (1, 2, 3, 4)

7. Which of the following carbocations have potential to rearrange?
CH3 
   CH2
(1) CH3 — C — C — O (2) (3) — CH (4)
CH3 CH3
CH3 CH 3
+
CH3—C + CO
+
 CH3—C—C = O
CH3 CH 3
+
CH—CH3 +
CH3

+ +
CH2

8. Formic acid is more acidic than

(1) Benzoic acid (2) Acetic acid
(3) Phenol (4) Benzene sulphonic acid
In benzoic acid +R effect of benzene in acetic acid. +I effect of CH3–group and in phenol formation of less
stable resonating structures makes formic acid more acidic.
9. Which of the following will have C  O bond length almost similar to C — O bond length?
O O
O
(1) (2) (3) (4) O  C  O
Sol. Answer (1, 2)

–
O
–
O
+ +
Both are aromatic.

10. The correct order of stability is/are
  
(1) HC  C  H2 C  CH  CH3  CH2 (2) HC  C > H C = CH > CH3–CH
2 2
CH2
  
(3) HC  C  H2 C  CH  CH3  CH2 (4)

 Due to percentage S-character (electronegativity) anion of sp hybridized carbon is most stable.
 Due to lower bond energy of allylic H as compared to benzylic H, allyl radical is more stable than benzyl
radical.
11. Which of the following is not stabilised by hyperconjugation?
Me Me

 
(1) CH3 (2) CH2 (3) (4) 
Me Me

 In CH3 and there is no  hydrogen
+
 In CH2 , stability is due to overlapping of p-orbital
12. Dichloro ethene shows

(1) Geometrical isomerism (2) Position isomerism (3) Metamerism (4) Chain isomerism
Sol. Answer (1, 2)
Cl
Cl – CH = CH – Cl can show geometrical isomerism and CH 2 CH is its position isomer
Cl
13. A compound having molecular formula C4H10O can show
(1) Metamerism (2) Functional isomerism (3) Chain isomerism (4) Position isomerism
Sol. Answer (1, 2, 3, 4)
All four isomerism are possible. Optical isomer is possible by 2-methyl-1-butanol.
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.
15. Consider the following compounds
N N
H NH2
(I) (II) (III)
Which of the following statements are correct?

(1) I is more basic than II (2) II is more basic than I and III
(3) III is more basic than II (4) I is weakly acidic
Sol. Answer (2, 4)
Due to higher Kb for II, it is more basic than I and II.
16. Which of the following correctly represent the acidic strength of given acids?
(1) Cl3CH > F3CH (2) CH3COOH > CH3CH2OH
OH OH
(3) H2O > CH3CH2OH (4) >
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

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
(3) (4) C6H5–CO–CH2–CO–CH3

NH2
C6H5 CHO has no –H. Therefore it will not exhibit tautomerism.
O O H
H 2N H NH2
20. Which of the following can exhibit geometrical isomerism?
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
21. The compounds which cannot react with NaOH is/are

OH
(1) CH3  C  CH (2) NH3 (3) C2H5OH (4)

OH– cannot neutrallise CH3—C  CH, NH3 and C2H5OH due to their very low acidic strength (weaker acids
than H2O).
22. The hybridisation of N is correctly given in
(1) sp3 in acetamide (2) sp2 in pyridine (3) sp2 in pyrrole (4) sp in methyl cyanide
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
Sol. Answer (1, 3)
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.
24. In the given compound the hybridisation states of C atom is/are not
(1) sp2 (2) sp3 (3) sp (4) dsp2
All carbon atoms are sp2 hybridised due to resonance.

25. In Lassaigne’s test, the sodium extract of an organic compound containing both N and S on treatment with FeCl3
solution produces a blood-red colour. The appearance of this blood red colour is due to
(1) [Fe(SCN)4]– (2) FeCl2(SCN) (3) [Fe(SCN)(H2O)5]2+ (4) Na4[Fe(CN)5NOS]

All of three are possible and (4) is Prussian blue coloured.
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
Sol. Answer (3)

In dienone phenol tautomerism phenol form is more stable due to its aromatic character.
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
3. Write IUPAC name of
3
4 2
1
5
6 4
3
1 2
(1) 5-(3,3-dimethyl cyclobutyl) 1,2,2,3-tetra ethyl cyclohexane

(2) 5-(3,3-dimethyl cyclobutyl) 1,3-diethyl 2,2-dimethyl cyclohexane
(3) 1,2,2,3-tetra ethyl 5-(3,3-dimethyl cyclobutyl) cyclohexane
(4) None of these
Sol. Answer (1)
Fact
Comprehension-III
Weak Acid does not dissociate completely into its ions. It is in equilibrium with its conjugate base. Greater is the
K
stability of conjugate base, greater is value of k for that equilibrium making the equilibrium move in (HA a H++A–)
forward direction. i.e., more is the degree of dissociation of that acid. Same is the case for weak bases. Factors
affecting the stability of conjugate acid or base are electronic effect like resonance effect and inductive effect acting
upon the species.
1. Which of the following is strongest acid?
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
Conjugate base of O2N C NO2 is
NO2
Stabilized by three strong electron withdrawing groups

i.e., O O

N C N
O O
N
O O
Stabilized by –I and –M effect of three –NO2 groups.
3. Which of the following is most basic due to +R effect of any substituent?
NH2 NH2 NH2

..
(1) N (2) (3) (4)
H
NO2 CH3 OCH3
Sol. Answer (4)

+R effect of –OCH3 predominates over –I effect.
Comprehension-IV
Hyperconjugation is defined as No bond resonance. The concept of hyperconjugation arose from the discovery
of electron releasing pattern for alkyl groups. It involves  electrons of C–H bond. Greater the number of C–H
bond (  -hydrogen atom w.r.t. double bond) more will be hyperconjugative structures, more will be stability. Heat
of hydrogenation of alkene are affected by hyperconjugative effects.
1. Which of the following is incorrect hyperconjugative structure?
H H H H
H C H H C H H C H H C H
(1) (2) (3) (4)
Sol. Answer (3)

H is released as H+ not as H–.
2. Which of the following has highest magnitude of enthalpy of hydrogenation?
(1) (2) (3) (4)
Sol. Answer (1)
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
1. Match the following.
Column-I Column-II
(Molecular formula) (Type of isomerism)
(A) C6H12O (p) Functional isomerism
(B) C4H11N (q) Geometrical isomerism
(C) C6H12 (r) Metamerism
(D) C5H12O (s) Tautomerism
(t) Position isomerism

Sol. Answer A(p, q, r, s, t), B(p, r, t), C(p, q, t), D(p, r, t)
C6H12O has one degree of unsaturation.
 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.
C6H12 can show ring chain isomerism.
Column-I Column-II
(Estimation) (Method)
(A) C (p) Liebig method
(B) H (q) Duma method
(C) N (r) Kjeldahl's method
(D) X (Chalcogen) (s) Carius method
Sol. Answer A(p), B(p), C(q, r), D(s)
Factual based
Column-I Column-II
(Estimation) (Percentage)
(A) 0.45 gm organic compound gives 1.1 gm (p) 66.6% C
CO2 and 0.3 gm H2O 7.4% H
(B) C : H : N ratio in compound 18 : 2 : 7 (q) 26% N
(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
Sol. Answer A(p), B(p, q), C(s), D(r)
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
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
(A) (p) Aromatic character
(B) CH3 — CH (q) Resonance

CH3
(C) (r) Hyperconjugation
(D) CH3 — O — CH2 (s) Inductive effect
Sol. Answer A(q), B(r, s), C(p, q), D(q, s)


is resonance stabilised but antiaromatic.
+
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)
More contributing Less contributing
 All C—C bonds are not equal.

2. STATEMENT-1 : p-Nitroaniline is more polar than nitrobenzene.
and
STATEMENT-2 : Nitro group has – M effect.
Sol. Answer (2)
Both statements are correct but reason for this is combined effect of –NO2 and –NH2.
3. STATEMENT-1 : All C—C bonds are equal in [10]-Annulene.
and
STATEMENT-2 : [10]-Annulene is a non-aromatic compound.
Sol. Answer (4)

All C—C bonds are not equal in [10]-Annulene.
HO O OH
4. STATEMENT-1 : is less acidic than

HO
O
Squaric acid
Phenol
and
STATEMENT-2 : Conjugate base of phenol is resonance stabilized.
Sol. Answer (4)
Infact squaric acid is more acidic than phenol.
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.
Sol. Answer (4)
Compound (X) will give only two moles of AgBr.
6. STATEMENT-1 : Bridge head carbocation is less stable than Bridge head carbanion.
and
STATEMENT-2 : C atom in carbocation is sp2 generally hybridized.
Sol. Answer (2)
Carbocation and carbanion are generally sp2 and sp3 hybridised.
7. STATEMENT-1 : Aldehydes and ketones having same molecular formulae are structural isomers.
and
STATEMENT-2 : Aldehydes and ketones are metamers.
Sol. Answer (3)
Aldehydes and ketones cannot be metamers.
8. STATEMENT-1 : Carbocationic rearrangement is known as electrophilic rearrangement.
and
STATEMENT-2 : Carbocations are stabilized by both hyperconjugation and +I effect.
Sol. Answer (4)
Carbocationic rearrangement is known as nucleophilic rearrangement.
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.
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?
Sol. Answer (4)
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+?
Sol. Answer (6)
3. On how many atoms positive charge is delocalized in the given ion?
Sol. Answer (4)
F F F F
Hence positive charge is delocalized over four atoms.
4. How many of the given species will behave as an electrophile?
CCl2, NH3, CH3, NH 4, CH 3, OH, BF3, AlCl3, Br
Sol. Answer (5)
–
NH3, NH4, CH3 and OH are not electrophiles, infact they are nucleophiles .
5. How many bicyclic isomers are possible for the molecular formula C6H12O?
Sol. Answer (0)
Index of hydrogen deficiency is 1.
 Bicyclic system is not possible for this.
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)
Sol. Answers (4)

Trinitrophenol, squaric acid, v and viii can give CO2 with NaHCO3.
7. How many total types of products are formed by dehydrohalogenation of 2-chlorobutane?
Sol. Answer (3)
1-Butene, Cis-2-butene,trans-2-butene
8. The total number of structural dihaloderivatives possible in n-pentane are ____.
Sol. Answer (9)
(1, 1), (1, 2), (1, 3), (1, 4), (1, 5), (2, 2), (2, 3), (2, 4), (3, 3)
Dihaloderivatives are nine different compounds.
9. Hydrocarbon P on complete combustion produce x mol of CO2 and y mol of H2O and x = 2y . 1 mol of P for
complete combustion required 7.5 mol of oxygen (O2) and P contain only C and H. The number of mol of
carbon atom in 1 mol of P are
Sol. Answer (6)
CxH2y + 7.5O2  xCO2 + yH2O
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)


CLS JEEAD-19-20 XI Che Target-5 Level-2 Chapter-12

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Level-II

3. Which process is suitable for purification of aniline?

(1) Simple distillation (2) Steam distillation

(3) Fractional distillation (4) Fractional crystallisation

Sol. Answer (2)

(1) I and IV will have nearly same barrier of rotation

(2) II and III will have nearly same barrier of rotation

(3) At room temperature I will have frozen rotation

(4) III will have relatively higher barrier of rotation as compared to IV

Sol. Answer (4)

In II and III charge separated structures are more contributing.

5. Arrange the given species in the increasing acidic strength :

Sol. Answer (3)

Stronger acids have more stable conjugate base.

6. Order of basicity of the following species is

is anti-aromatic while is aromatic.

9. Species in which all C—C bonds are equal is

(1) (2) (3) (4)

Sol. Answer (2)

Percentage axial conformer = 5%

Sol. Answer (1)

(1) (2) (3) B—R (4) All of these

Sol. Answer (3)

(1) II and I (2) IV and II (3) III and II (4) II and IV

pKa of these acids are

(1) (2) (3) (4)

Sol. Answer (1, 2, 3, 4)

Sol. Answer (1, 3, 4)

(1) C4H10O (2) C4H11N (3) C4H8O (4) C4H9Cl

Sol. Answer (1, 2, 3)

(1) (2) (3) (4)

Sol. Answer (2, 3)

6. Which of the following carbocation is stabilised by resonance?

Sol. Answer (1, 2, 3, 4)

8. Formic acid is more acidic than

Sol. Answer (1, 2)

Both are aromatic.

Sol. Answer (2, 3, 4)

11. Which of the following is not stabilised by hyperconjugation?

12. Dichloro ethene shows

13. A compound having molecular formula C4H10O can show

Sol. Answer (1, 2, 3, 4)

All four isomerism are possible. Optical isomer is possible by 2-methyl-1-butanol.

Sol. Answer (1, 2, 3)

15. Consider the following compounds

Which of the following statements are correct?

(3) H2O > CH3CH2OH (4) >

(3) (4) C6H5–CO–CH2–CO–CH3

20. Which of the following can exhibit geometrical isomerism?

21. The compounds which cannot react with NaOH is/are

(1) CH3  C  CH (2) NH3 (3) C2H5OH (4)

Sol. Answer (1, 2, 3)

Sol. Answer (1, 3)

(1) sp2 (2) sp3 (3) sp (4) dsp2

Sol. Answer (2, 3, 4)

All carbon atoms are sp2 hybridised due to resonance.

(1) [Fe(SCN)4]– (2) FeCl2(SCN) (3) [Fe(SCN)(H2O)5]2+ (4) Na4[Fe(CN)5NOS]

All of three are possible and (4) is Prussian blue coloured.

Sol. Answer (3)

(1) 5-(3,3-dimethyl cyclobutyl) 1,2,2,3-tetra ethyl cyclohexane

Conjugate base of O2N C NO2 is

Stabilized by three strong electron withdrawing groups