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ALKANES JEE ADVANCED - VOL - IV

ALKANES
Alkanes: Physical Properties
The alkanes can exist as gases, liquids, or solids at room temperature. The unbranched alkanes
methane,ethane, propane, and butane are gases; pentane through hexadecane are liquids; the homologues
larger than hexadecane are solids.
Branched alkanes normally exhibit lower boiling points than unbranched alkanes of the same carbon content.
This occurs because of the greater van der Waals forces that exist between molecules of the unbranched
alkanes. These forces can be dipole dipole, dipole induced dipole, or induced dipole induced dipole in
nature. The unbranched alkanes have greater van der Waals forces of attraction because of their greater
surface areas.
Solid alkanes are normally soft, with low melting points. These characteristics are due to strong repulsive
forces generated between electrons on neighboring atoms, which are in close proximity in crystalline solids.
The strong repulsive forces counterbalance the weak van der Waals forces of attraction.
Finally, alkanes are almost completely insoluble in water. For alkanes to dissolve in water, the van der
Waals forces of attraction between alkane molecules and water molecules would have to be greater than
the dipole dipole forces that exist between water molecules. This is notthecase.
Alkanes: Enthalpy of Combustion
Alkanes can be oxidized to carbon dioxide and water via a free radical mechanism. The energy released
when an alkane is completely oxidized is called the heat of combustion. For example, when propane is
oxidized, the heat of combustion is 688 kilocalories per mole.
In a homologous series like the straight chain alkanes, the energy liberated during oxidation increases by
approximately 157 kilocalories for each additional methylene (CH 2) unit.
Heat of combustion data is often used to assess the relative stability of isomeric hydrocarbons.Because the
heat of combustion of a compound is the same as the enthalpy of that compound in its standard state, and
because potential energy is comparable to enthalpy, the differences in heats of combustion between
two alkanes translate directly to differences in their potential energies. The lower the potential energy of
a compound, the more stable it is. In the alkanes, the more highly branched isomers are usually more stable
than those that are less branched.
Halogenation
Selectivity
When alkanes larger than ethane are halogenated, isomeric products are formed. Thus chlorination of
propane gives both 1-chloropropane and 2-chloropropane as mono-chlorinated products. Four
constitutionally isomeric dichlorinated products are possible, and five constitutional isomers exist for the
trichlorinated propanes. Can you write structural formulas for the four dichlorinated isomers?

The halogenation of propane discloses an interesting feature of these reactions. All the hydrogens in a
complex alkane do not exhibit equal reactivity. For example, propane has eight hydrogens, six of
them being structurally equivalent primary, and the other two being secondary. If all these hydrogen
atoms were equally reactive, halogenation should give a 3:1 ratio of 1-halopropane to 2-halopropane
mono halogenated products, reflecting the primary/secondary numbers. This is not what we observe. Light
induced gas phase chlorination at 25 C gives 45% 1-chloropropane and 55% 2-chloropropane.
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CH3-CH2-CH3 + Cl2 >45%CH3-CH2-CH2Cl + 55% CH3-CHCl-CH3


The results of bromination ( light-induced at 25 C ) are even more suprising, with 2-bromopropane
accounting for 97% of the mono-bromo product.
CH3-CH2-CH3 + Br2>3%CH3-CH2-CH2Br + 97% CH3-CHBr-CH3
These results suggest strongly that 2-hydrogens are inherently more reactive than 1-hydrogens, by a
factor of about 3:1. Further experiments showed that 3-hydrogens are even more reactive toward halogen
atoms. Thus, light-induced chlorination of 2-methylpropane gave predominantly (65%) 2-chloro 2-
methylpropane, the substitution product of the sole 3-hydrogen, despite the presence of nine 1-hydrogens
in the molecule.
(CH3)3CH + Cl2 >65%(CH3)3CCl + 35% (CH3)2CHCH2Cl
It should be clear from a review of the two steps that make up the free radical chain reaction for halogenation
that the first step (hydrogen abstraction) is the product determining step. Once a carbon radical is
formed, subsequent bonding to a halogen atom (in the second step) can only occur at the radical site.
Consequently, an understanding of the preference for substitution at 2 and 3-carbon atoms must come
from an analysis of this first step.
First Step: R3CH + X >R3C + H-X
Second Step: R3C + X2 >R3CX + X
R (in RH) methyl ethyl i-propyl t-butyl
B.D.E. 103 98 95 93
phenyl benzyl allyl
110 85 88
B.D.E. = Bond Dissociation Energy(kcal/mole)
The difference in C-H bond dissociation energy reported for primary (1), secondary (2) and tertiary (3)
sites agrees with the halogenation observations reported above, in that we would expect weaker bonds
to be broken more easily than are strong bonds. By this reasoning we would expect benzylic and allylic
sites to be exceptionally reactive in free radical halogenation, as experiments have shown. The methyl
group of toluene, C6H5CH3, is readily chlorinated or brominated in the presence of free radical initiators
(usually peroxides), and ethylbenzene is similarly chlorinated at the benzylic location exclusively. The
hydrogens bonded to the aromatic ring (referred to as phenyl hydrogens above) have relatively high bond
dissociation energies and are not substituted.
h
C6 H 5 CH 2 CH 3 + Cl2 C6 H 5 CHClCH 3 + HCl
Since carbon-carbon double bonds add chlorine and bromine rapidly in liquid phase solutions, free radical
substitution reactions of alkenes by these halogens must be carried out in the gas phase, or by other
halogenating reagents. One such reagent is N-bromosuccinimide (NBS), shown in the second equation
below. By using NBS as a brominating agent, allylic brominations are readily achieved in the liquid phase.

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The covalent bond homolyses that define the bond dissociation energies listed above may are described
by the general equation:
R3C-H + energy >R3C + H
Since the hydrogen atom is common to all the cases cited here, we can attribute the differences in bond
dissociation energies to differences in the stability of the alkyl radicals (R3C) as the carbon substitution
changes. This leads us to the conclusion that:
alkyl radical stability increases in the order: phenyl < primary (1) < secondary (2) < tertiary
(3) < allyl H < benzyl.
Because alkyl radicals are important intermediates in many reactions, this stability relationship will prove to
be very useful in future discussions. The enhanced stability of allyl and benzyl radicals may be attributed to
resonance stabilization. Formulas for the allyl and benzyl radicals are shown below. Draw structural formulas
for the chief canonical forms contributing to the resonance hybrid in each case.

The poor stability of phenyl radicals, C6H5, may in turn be attributed to the different hybridization state of
the carbon bearing the unpaired electron (sp2 vs. sp3).
Since the H-X product is common to all possible reactions, differences in reactivity can only be attributed
to differences in C-H bond dissociation energies. In the case of carbon-hydrogen bonds, there are significant
differences, and the specific dissociation energies (energy required to break a bond homolytically) for
various kinds of C-H bonds have been measured. These values are given in the following table.
alkyl radical stability increases in the order: phenyl < primary (1) < secondary (2) < tertiary
(3) < allyl H benzyl.
Because alkyl radicals are important intermediates in many reactions, this stability relationship will prove to
be very useful in future discussions. The enhanced stability of allyl and benzyl radicals may be attributed
to resonance stabilization.Formulas for the allyl and benzyl radicals are shown below. Draw structural
formulas for the chief canonical forms contributing to the resonance hybrid in each case.

The poor stability of phenyl radicals, C6H5, may in turn be attributed to the different hybridization state of
the carbon bearing the unpaired electron (sp2 vs. sp3).

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LEVEL-IV

STRAIGHT OBJECTIVE QUESTIONS

1. Observe the following reaction sequence

X Br2 /hv Y Mg/Ether Z W dil. H2SO4 U O3 / Zn /H2O


X can be

CH 3
a) b) c) d)

2. Which of the following is correct potential energy diagram for the given chain propagating step.


CH 3 H F
CH 3 H F H 32 kcal / mol
B . E . 435 kJ / mol B . E . 569 kJ / mol


* *
F ........H......C H3
*
CH 4 F *
C H 3 HF
*
C H 3 HF H East 32 kcal mol 1
a) b)
H East 32 kcal mol1 *
CH 4 F


* * * *
C H 3 ....H..... F F .....H..... C H 3
*
CH 4 F Eact 5.0 kJ mol 1
*
C H 3 HF *
c) d) C H 3 HF
H 32 kcal mol 1
CH 4 F
*
Eact 32 kcal mol1

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3.

a) b)

c) d)

The deuterium kinetic isotope effect for chlorination of an alkane is defined as follows :

4. Which of the following is correct comparison for the above effect ?


Rate of homolytic clevage of C-H bond by Cl
Deuterium Kineticisotopic effect=
Rate of homolytic clevage of C-D bond by Cl
a) IBr IC1 b) IBr IC1 c) IBr IC1 d) cannot be predicted
5. In the given conformation if C2 is rotated about C2 C3 bond anti clockwise by an angle of 1200
then the conformer obtained is

a) Fully eclipsed b) Partly elipsed c) Gauche conformer d) Anti-confirmer

MULTIPLE CORRECT ANSWER TYPE QUESTIONS

82 82
6. Radioactive Br Br adds to 1- bromocyclohexene. The product is

a) is 1,1,2- tribromocyclohexane b) has radioactive bromine at vicinal positions
c) has radioactive bromine trans to each other d) has radioactive bromine cis to each other

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7. CH 4 is not obtained by
a) Wurtz reaction b) Corey-house synthesis
c) Reduction of alkylhalide d) kolbes electrolysis

LINKED COMPREHENSION TYPE QUESTIONS

Passage-1: In the study of chlorination of propane, four products (A,B,C&D) of the formula
C3 H 6Cl2 were isolated. Each was further chlorinated to provide trichloro products C3 H 5Cl3 .
It was found that A provide one trichloro product, B gave two and C&D each gave three. It is
found that D is optically active.
8. Formula of the compound A is

a) b) c) d)

9. Correct formula of the product of chlorination of B is -

a) b) ClCH 2CHClCH 2Cl c) Both A and B d)

10. Correct formula of the compound D is


a) b) c) d)
Passage-2:
Wurtz reaction involves the condensation of two molecules of alkyl halides in the presence of
sodium and dry ether

R - X + 2Na + R - X dry ether R - R + 2NaX

In this reaction small amount of alkene is also formed as by-product.

Tertiary alkyl halides do not give Wurtz reaction. Frankland reaction is similar but has certain
advantages over Wurtz reaction. It is useful in the synthesis of symmetrical alkanes. Frankland
reaction is shown by primary, secondary as well as tertiary alkyl halide.
11. Among all isomers of hexane which of the following isomer cannot be obtained in a good yield by
Wurtz reaction (from symmetrical alkyl halides)?
1) n-hexane 2) iso hexane 3) 2,3,-dimethyl butane 4) Neo hexane
a) 1,4 b) 2,4 c) 1,3 d) 3,4
12. Which among the following compounds will give Wurtz reaction with good yield?
a) CH 2 CH Br b) ph Br
c) CH 2 CH CH 2 Br d) CH 3 CH CH Br .

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13. A mixture of ethyl iodide and methyl iodide is subjected to Wurtz reaction. The product that will
not be formed is
a) Ethane b) Butane c) Propane d) Pentane

MATRIX MATCH TYPE QUESTIONS

14. Column I Column II


Li CH 3CH 2Cl
A) CH 3CH 2Cl
Cul
? p) (CH3)2CHCH2CH(CH3)2
Li CH 3 2 CHCH 2 Br
B) CH 3 2 CHI
Cul
? q) CH 3CH 2CH 2CH 3
Li CH3CH2Br
C) CH3CH2C CH3 Br
Cul
? r) CH 3 3 CCH 2CH 3

Li CH3CH2Br
D) (C H 3)3C C l s) CH 3CH 2C CH 3 2 CH 2CH 3
CuI

15. Match the Column that are used to get cyclohexane.

Column I Column II

A) (p) Electrolysis followed by H 2 / Ni

COONa
B) (q) NaOH CaO /

C) Br2CH 2 CH 2 4 CH 2 Br (r) H 2 / Ni /

COONa

D) (s) Zn /
COONa

ASSERTION-REASONING TYPE QUESTION

16. Statement - 1: Alkanes are monochlorinated with (CH 3 )3 COCl.


Statement - 2: The initiating step is the heterolytic cleavage of hypochlorite
a) Statement - 1 is true, Statement - 2 is true; Statement - 2 is a correct explanation for Statement - 1.
b) Statement - 1 is true, Statement - 2 is true; Statement - 2 is NOT a correct explanation for Statement
-1
c) Statement - 1 is True, Statement - 2 is False
d)Statement - 1 is False, Statement - 2 is True.
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INTEGER ANSWER TYPE QUESTIONS

17. The number of types of monochloroalkanes formed by chlorination of isobutane is


18. The number of moles of CH 4 formed by reacting 96 grams of CH 3OH with excess CH 3 MgI is
19 The number of structural isomers of alkane containing six carbon atom is
20. The number of different types of substitution products possible when bromine and ethane react
in presence of light is
21. The maximum number of carbon atoms in the expected products of the following reaction

CH 3CH 2 Br + CH 3 - CH - CH 2 Br
CH 3
Na / Ether
Product

22 The number of possible enantiomeric pairs that can be produced during monochlorination of
2-methylbutane is

CH 3
Cl2 , hv
isomeric products
23 (including sterioisomers)
H 3C C5 H11Cl
CH 3

24. is mono chlorinated through free radical substitution reaction. What is the total number

of possible optical isomers that can be formed.

SUBJECTIVE TYPE QUESTIONS

25. Chlorination of optically active 2-chlorobutane yields a mixture of isomers with the formula
C4H8Cl2
a) How many different isomers would you expect to be produced? What are their structures?
b) Which of these fractions would be optically active?
26. Two isomeric organic compounds (A) and (B) of molecular formula C4H8Br2 on hydrolysis gave
two compounds (C) and (D) of formula C4H8O. (C) and (D) gave two isomeric acids (E) and (F) of
formula C4H8O2 on oxidation. Both the acids on decarboxylation with soda-lime gave propane.
Identify (A) to (F).
27. n-Butane is produced by the monobromination of ethane followed by Wurtz reaction. Calculate
the volume of ethane at STP required to produce 55 g n-butane, if the bromination takes place
with 90% yield and the Wurtz reaction with 85% yield.

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KEY
LEVEL -IV

STRAIGHT OBJECTIVE QUESTIONS

1) A 2) D 3) C 4) A 5) C

MULTI CORRECT ANSWER

6) A,B,C 7) A,B,D

LINKED COMPREHENSION TYPE QUESTIONS

8) B 9)C 10) D 11) B 12) C 13) D

MATRIX MATCHING TYPE QUESTIONS

14) (A q), (B p), (C s), (D r) 15) (A-r) , (B- q) ,(C- s), (D- q)

ASSERTION-REASONING TYPE QUESTIONS

16) C 17) 2 18) 3 19) 5 20) 9 21) 8


22) 2 23) 6 24) 8

HINTS

LEVEL-IV

STRAIGHT OBJECTIVE QUESTIONS

1.

3 Aromatisation

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4 Because a bromine radical is less reactive than a chlorine radical , a bromine radical has a greater preference
for the more easily broken C-H bond. Bromination , therefore would have a greater deuterium kinetic
isotope effect than chlorination
5 Conceptual

MULTIPLE CORRECT ANSWER TYPE QUESTIONS


82 82 82 82
6 Br Br Br Br
Br
82
82 Br Trans addition
Br
Br 82
Br
Br
82 Br
Br H
7 Conceptual

LINKED COMPREHENSION TYPE QUESTIONS

(B)

(C)
(D)

9.

(B)
(C)
(D)

10.

(B)

(C)
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(D)
11. Conceptual
12. Conceptual
13. Conceptual

MATRIX MATCHING TYPE QUESTION

15. Conceptual

INTEGER ANSWER TYPE QUESTIONS

CH 3 CH 3 CH 3

17. CH CH 3 Cl 2

h
CH CH 2 Cl + CH 3 c Cl
CH 3 CH 3 CH 3

CH 3OH CH 3 MgI CH 4 Mg OH I
18. 32 g 1 mole
96 g 3 mole
CH3 CH3
H3C
H3C H3C H3C
CH3 H 3C
19. CH3
, , CH3, H C
3
, CH3
CH3 H3C CH3 H 3C
20. Monosubstituted =1, disubstituted=2, trisubstituted =2
tetrasubstotuted = 2, pentasubstituted=1, hexasubstited=1
Total =9
CH 3 CH 3
CH 3

21. 2 CH CH 2 Br
Na / Ethers CH CH 2 CH 2 CH

CH 3 CH 3 CH 3

CH 3 CH 3

H c CH 2 Cl Cl CH 2 c H
22. C2 H 5 C2 H 5 CH3 CH(CH 3 )CH(Cl)CH 3 and its mirror image

CH 3
CH 2 Cl
23.
CH 3 c Cl
CH 3 CH CH 2 CH 3
C2 H 5
(d & l)
CH 3
CH3 CH(CH 3 )CH(Cl)CH 3 and its mirror image
CH 3 CH CH 2 CH 2 Cl
Total isomeric products = 6
24). 2 - Methyl and 3 - Methyl chloro-cyclohexanes can have optical isomerism

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SUBJECTIVE TYPE QUESTIONS
CH3 CH2Cl CH3 CH3
CH3
CCl2 CHCl CHCl CHCl
25. a)H3C Cl Cl2

CH2 CH2 CHCl CH2
CH2CH3
CH3 CH3 CH3 CH2Cl
4 possible isomers
b)The compounds which are having chiral centres (asymmetric carbon) will be optically active
CH2 Cl CH3 CH3

Cl H H Cl H Cl
; ;
C2 H 5 Cl H CH2
CH3 CH2Cl
(I) (II) (III)
Three fractions are optically active
H3C Br
H3C Br H3C
H3C O
O
26. A D
Br H3C Br C H3C
B
OH
H3C
O H3C
E O
F
HO H3C
27. 55.57 Lts

LEVEL-V
STRAIGHT OBJECTIVE QUESTIONS
1.
CH2 Cl
Na (Dry ether)
CH3
CH2 Cl
Product Obtained in above Wurtz reaction is:
CH3

a) b)

CH3 CH3 CH3

c) d) Both (a) and (b)

CH3 CH3

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2. An alkane C7 H16 is produced by the reaction of lithium di(3-pentyl) cuprate with ethyl bromide.
The structural formula of the product is
a) 3-ethylpentane b) 2-ethylpentane c) 3-methylhexane d) 2-methylhexane
3. What is the IUPAC name for the following compound?
H CH3

CH3 H
a) dimethylcyclohexane b) 1,3-dimethylcyclohexane
c) cis-1,3-dimethylcyclohexane d) trans-1,3-dimethylcyclohexane
4. The most stable conformational isomer of cis-1-bromo-2-chlorocyclohexane will have...
a) both halide atoms in axial positions. b) both halide atoms in equatorial positions.
c)the bromine atom in an axial position and the chlorine atom in an equatorial position.
d) the bromine atom in an equatorial position and the chlorine atom in an axial position.
5. The most stable conformational isomer of trans-1-ethyl-2-methylcyclohexane will be...
Et
Et H
H
Et Et
H H H
H
a) CH3 b) c) CH3 d)
H H3C H CH3

6. Which Newman projection shows the most stable conformation of the following compound?

Br H H

Cl H Br

7. Which of the these compounds represents the major monochlorination isomer formed in the
following reaction?

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8. How many dichlorinated isomers can be formed by the halogenation of CH3CH2CH2CH3 with Cl2
in the presence of light?
A) 2 B) 3 C) 5 D) 6
9. Which of the following cycloalkanes has the smallest heat of combustion per CH2 group?
A)cyclopropane B)cyclobutane C)cyclopentane D)cyclohexane
10. Which has the greatest molar heat of combustion?
A) trans-1,2-dimethylcyclopentane B) cis-1,2-dimethylcyclopentane
C) trans-1,3-dimethylcyclopentane D) methylcyclohexane

MORE THAN ONE ANSWER QUESTIONS

11. Which of the following alkanes cannot be synthesized by the Wurtz reaction in good yield?

a) b) c) d)

LINKED COMPRENHESION TYPE QUESTIONS

Passage-1:
Halogenation is a substitution reaction, where halogen replaces one or more hydrogens of hydrocarbon.
h
R H X 2 R X HX

Chlorine free radical make 10 , 20 ,30 radicals with almost equal ease, where as bromine free radicals have
a clear preference for the formation of tertiary free radicals. So, Bromine is less reactive, and more selective
whereas chlorine is less selective and more reactive.
30 20 10
The relative rate of abstraction of hydrogen by Br is (1600) (82) (1)

30 20 10
The relative rate of abstraction of hydrogen by Cl is (5) (3.8) (1)
Consider the above argument and answer the following:
12. 1-halo-2,3-dimethyl butane will be obtained in better yields, if halogen is:
a) Br2 b) Cl2 c) I2 d) Cant be predicted
CH3 CH3
X
X 2 / h
13.

Above product will obtained in better yield if X is


a) Cl2 b) I2 c) Br2 d) Cant be predicted

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CH 3
14. |
Cl 2 / h
CH 3 CH CH 3 Product
Major product in the above reaction is
CH 3
CH 3 |
| CH 3 CH CH3
a) b) |
CH 3 CH CH 2 Cl
Cl

CH 3 CH CH 2 CH3
c) CH 3 CH 2 CH 2 Cl d) |
Cl

ASSERTION REASONING TYPE QUESTIONS:

Directions: In each of the following questions, a statemenet of assertion (A) is given and a
corresponding statement of reason (R) is given just below it. Of the two statments, mark the
correct answer as.
a) If both A and R are true and R is the correct explanation of A
b) If both A and R are true and R is not the correct explanation of A
c) If A is true but R is false
d) If A is false and R is true
H Br
H3C D
15. Assertion (A): When H is subjected to dehydrohalogenation using NaOEt/EtOH,
H

the product contains no deuterium.


Reason (R): E2 follows anti elimination.

INTEGER TYPE QUESTIONS

16. Identify number of chiral centers present in product obtained by following reaction:
Br2
CCl4

CH3 H
ADDITIONAL QUESTIONS

1. The number of carbons in simplest optically active alkane.


2. The number of possible enantiomers of simplest possible optically active alkane of formula
Cx H y .
3. The number of Primary carbons in the branched isomer of first simplest alkane that react with
bayers reagent to give alcohol.
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4. The number of dichloro derivatives of propane is equal to number of mono chloro derivatives of
C x H y ( straight chain alkane). The number of possible isomers for this compounds including
stereo isomers.
5. Sequence that represents progressive difference between number of hybrid to pure orbitals
involved in homologues series of alkanes.
a) 1,3,5,7,.... b) 2,4,6,8,.... c) 1,2,3,4... d) 1,4,9,16,......
6. A( C x H y , alkane where x = 6) undergoes aromatisation in presence of a catalyst to form compound
B which on reduction with H 2 / Ni form compound C. Difference in number of hydrogens of C
and A.
a) 2 b) 4 c) 6 d) 8
Na
7. t-Butylchloride
DryEther
X(major)
Number of SP 2 hybridised carbons present in the product molecule.

Column - I Column - II
a) CH Cl
h
Products p) CH3Cl
4 2
excess (Possible)

b) Will not react with amm. AgNO3 q) CH2Cl2


8. c) Have dipole moment r) CHCl3
O Cl2
d) s) CCl4
NaOH Products

KEY
LEVEL-V
STRAIGHT OBJECTIVE QUESTIONS
1. D 2.A 3.D 4. D 5.C 6. A 7. B 8.D
9. D 10. B
MORE THAN ONE CORRECT ANSWER
11. A,C,D
LINKED COMPREHENSION QUESTIONS
12. B 13. C 14.A
ASSERTION AND REASON
15.A
INTEGER TYPE
16.3
ADDITIONAL QUESTIONS
1. 7 2. 4 3. 3 4. 11 5. B 6. A 7. 2
8. (A p, q, r ,s), (B r, s), (C p,q,r), (D r)

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HINTS

LEVEL -V

1. Wurtz reaction

CH3CH2
CH CuLi+BrCH2CH3
2. CH3CH2
2

CH 2 CH 3
|
CH 3CH 2 CHCH 2 CH 3 (CH3CH 2 )2 CHCu LiBr
8. The products are (1,1), (1,2), (1,3), (1,4), (2,2), (2,3) dichlorobutanes.

LINKED COMPREHENSION QUESTIONS

C C
12. , Cl2 is less selective
x-C-C-C-C
10 halide will be obtained in better yield
13. To obtain 30 halide Br2 must be used.
CH 3
14. |
CH 3 CH CH 2 Cl
Relative formation is 9 1
% yield 9 /14 100
ASSERTION AND REASON
Br
H 3C D CH3
EtO
15.
EtOH

(Hoffmann product due to anti-coplanarity between H and Br)

INTEGER TYPE
16.
Br
Br2
CCl4
Br
H3C H H3C H

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