Al kane :

(a) Definition :
Saturated hydrocarbons having the general formula CnH2n+2 constitute the homologous series of
alkanes.
Ex. CH4 , C2H6 , C8H8 , C4H10, C10H22, C100H202
(b) Bonding parameters of hydrocarbons :

Bond Energy
Bond Type Bond Length A° Bond Order
(kJ/mole)
C–H 400 – 415 1
sp – S
3
1.09
sp – S
2
1.08
sp – S 1.08
C–C
sp – sp
3 3
1.54 80 – 85 kcal/mol
sp – sp
3
1.47
sp – sp
2 2
1.48
sp – sp
2
1.43
sp – sp 1.38
C=C 610 – 630 2
CH2 = CH2 1.34 140 – 145 kcal/mol
sp – sp
2 2
1.32
sp – sp
2
1.31
sp – sp 1.28
CC 835 3
sp – sp 1.20 180 – 185 kcal/mol

(c) Nomenclature of alkanes (Examples)

2, 3, 5-Trimethylhexane

4-Ethyl-2, 3, 5-trimethylheptane

3,3,5-Triethyl-2, 2, 5, 6, 6-pentamethylheptane

1
 (d) Isomerism in alkanes :
(I) Strutural Isomerism
(a) Chain Isomerism :

C4H10 : &

C5H12 : , &

C6H14 : , &

C6H12 : &

(b) Positional isomerism :

C6H14 : &

C8H16 : , &

(II) Stereoisomerism
(a) Optical Isomersion :

& Optical isomers of C7H14

(b) Conformational isomers :

Conformati onal
Isomers of
Bu tan e

Pr epar at i on of Al kanes :
1. By catalytic hydrogenation of alkenes / alkynes

R – CH2 – CH2 – R

R – CH2 – CH2 – R

e.g. CH3 – CH = CH – C2H5 CH3 – CH2 – CH2 – C2H5

C 2H5 C 2H5
| |
CH3  C  CH  C 2H5 (±) CH3  CH  C 3H7

CH3 – C  C – C2H5 CH3 – CH2 – CH2 – C2H5

Reagent : H2 + transition metal catalyst in the form of very fine particles suspended
in solvent (CH3COOH or C2H5 – OH or H2O) Ni, Pt, Pd, Ru, Rh metals
can be used.
Condition : Temperature = Room temperature (25 – 30°C)
Pressure = High pressure of H2 gas

2
2. From alkyl halides :
(A) From organometallics
(i) By wurtz Synthesis
2R-X + 2Na   R – R + 2NaX.
ether

R – X + Na + R – X 
 R – R + R – R + R – R + 2NaX
ether

 CH3 – CH3 + 2NaI

2CH3I + 2Na 
ether
e.g. (i)

 C2H5 – C2H5 + 2NaI

2C2H5I + 2Na 
ether
(ii)

+ Na 
 + CH3 – C2H5 + NaI
ether
(iii) 2

Ph – X Et
 Ph – Ph (fitting reaction)
Na
(iv) 2O

Ph – CH2 – X Et
 Ph – CH – CH – Ph
Na
(v) 2O 2 2

CH3 CH3 CH3

| | |
(vi) CH3 – CH – CH2 – X  CH3  CH  CH2  CH2  CH  CH3
Na
Et O 2



(vii) Na
ether

CH3
|
(viii) CH3  C  Cl 
Na
ether
|
CH3

Condition : The alkyl halide must be 1° or 2°. With 3° alkyl halide elimination product is formed.
Sodium is added in ethereal solution of R-X and a higher alkane containing even number of carbon
atom is formed. It is an SN2 reaction where Alkyl sodium (RNa) functions as a strong nucleophile.
If tertiary R-X is used the disproportionation reaction takes place and a mixture of an alkane and an
alkene is obtained (containing same no. of carbon atom as present in R-X).

(ii) By Frankland’s reaction :

2R – X + Zn  
 R – R + ZnX2
ether

2CH3I + Zn  
 CH3CH3 + ZnI2
ether
e.g.

(iii) From Grignard reagents


RMgX 
H
 RH

CH3CH2MgBr 2 CH3 – CH3 + Mg(OH)Br

HO
e.g.

Reagent : Any compound with active (acidic) hydrogen atom can be used
(iv) By corey-house synthesis (Gilmann reagent)

 R  Li 
2 Li
RX
CuX
(1) ( 2)
May be Alkylithiu m
1, 2, 3  Lix

3
 CH3Br + 2Li    CH3Li + LiBr
ether
e.g. (i)
2CH3Li + CuI  (CH3)2CuLi + LiI
(CH3)2CuLi + C2H5Br  CH3 – C2H5 + CH3Cu + LiBr

(ii) (C2H5)2CuLi + CH3 – X  CH3 – CH2 – CH3

CH3
|
(iii) + CH3 –X  CH3  C  CH3
|
CH3

   
C6H5 – Cl
(1) Li
(iv) ( 2) CuCl

(3)

Reagent : R2CuLi (Lithium dialkylcuperate = Gilmann reagent)

It is a milder reagent than Grignard reagent

Note : The gilmann reagent can be used in the presence of ester and amides. It is mainly
used for synthesis of unsymmetrical higher alkanes.

(B) By reduction of alkyl halides : (with metal and acid)

R – X    R – H + HX
Metal / acid

e.g. CH3 – I + 2[H]  CH4 + HI.

C2H5 – I + 2[H]  C2H6 + HI.

Reagents : Zn + HCl or
Zn + CH3COOH or
Zn – Cu couple + C2H5OH , (most commonly used)

(C) By reduction with LiAlH4.

R – X + LiAlH4   R – H + LiAlH3X
e.g. C3H7Cl + LiAlH4  C3H8 + LiAlH3X
Condition : Alkyl halide should be 1° or 2°.
(3° RX gives Elimination reaction)

3. From fatty acids :

(a) By Soda-lime method

RCOONa + NaOH 

CaO
RH + Na2CO3
sodium salt alkane
of acid

CH3COONa + NaOH   CH4 + Na2CO3

CaO
e.g.

The alkane formed has one carbon less than the carboxylic acid used.

(b) By Kolbe’s electrolysis

2RCOOK + 2HOH    
 RR + 2CO2 + H2 + 2KOH
Electrolysis

2CH3 – COOK + 2H2O    

 CH3CH3 + 2CO2 + H2 + 2KOH.
Electrolysis
e.g.
If n is the number of carbon atoms in the salt of carboxylic acid, the alkane formed has
2(n–1). Carbon atoms.

4
 (c) By reduction of fatty acids with hydroiodic acid :
R  COOH + 6HI  R  CH3 + 2H2O + 3I2
Acid alkanes
e.g. CH3 – COOH + 6HI  CH3 – CH3 + 2H2O + 3I2
Alkanes formed through this method contains same number of carbon atoms as in the
carboxylic acid.
5. Reduction of aldehydes, ketones :
(a) By Clemmensen’s reduction : with Zn – Hg / conc. HCl
Zn  Hg / conc . HCl
R – CHO     
 RCH + H O
3 2

O
|| Zn  Hg / conc . HCl
R  C  R       RCH2R + H2O

Zn  Hg / conc . HCl
CH3 – CHO      
 CH3CH3 + H2O

e.g.

O
||
Zn  Hg / conc . HCl
CH3  C  C 2H5 + 4[H]       CH3CH2C2H5 + H2O
Clemmensen reduction is not used for compounds which have acid sensitive group.

(b) By Wolff-kishner reduction with NH2NH2 / KOH

RCHO    
 RCH3
2 2 NH NH / KOH


RCO – R    
 RCH2R
2 2 NH NH / KOH

Wolff-kishner reduction is not used for compounds which have base sensitive groups.

(c) Reduction of aldehydes, ketones alcohols & fatty acids with conc. HI & red
phosphorus :

R – CH2 – OH + 2HI   R – CH3 + H2O + I2

Re d P
150C

R – CHO + 4HI    R – CH + H O + 2I
Re d P
150C 3 2 2

R – COOH + 6HI   R – CH3 + 2H2O + 3I2

Re d P
150C
6. By the action of water on carbides :
Al4C3 + 12H2O  3CH4 + 4Al (OH)3
Be4C + 4H2O  CH4 + 4Be(OH)2

7. By electric ark method :

C
C + 2H2 1200
  CH4
electric ark

1200 C
2C + 3H2 electric
  C H
ark 2 6

8. By Desulfurisation of :

R – S – S – R + H2    R – H + RH + 2S
Raney Ni

R – SH 2    
 2R – H + S
H ; Raney Ni

RSR 2    
 RH + RH + S
H ; Raney Ni

5
Physi cal Pr oper t i es of Al kanes :
1. Physical state :
The first four members (C1 to C4) are gases ; the next thirteen members, (C5 to C17) are liquids while
the higher members are waxy solids.
2. Boiling points :
The boiling points of n-alkanes increase regularly with the increase in the number of carbon atoms.

Among the isomeric alkanes, the branched chain isomers have relatively low boiling points as
compared to their corresponding straight chain isomers. Greater the branching of the chain, lower
is the boiling point. This is due to the fact that branching of the chain makes the molecule more
compact and brings it close to a sphere, so the magnitude of VDM forces decreases.

3. Melting Points
It is evident that the increase in melting point is relatively more in moving from an alkane having odd
number of carbon atoms to the higher alkane with even no. of ‘C’ while it is relatively less in moving
from an alkane with even number of carbon atoms to the higher alkane. Explanation : The alkanes
with even no. of ‘C’ atoms are more closely packed.

4. Solubility
In keeping with the popular rule “like dissolves like” hydrocarbons are insoluble in polar solvent like
water because they are predominantly non-polar in nature.

5. Density
The densities of alkanes increase with increasing molecular weight but become constant at about
0.8 g cm–3. This means that all alkanes are lighter than water.

6
Mel t i ng Poi nt & Boi l i ng Poi nt of Al kanes :

M.p., °C B.p., °C
Relative density
(at 20° C)
Name

Methane – 183 – 162

Ethane – 172 – 88.5
Propane – 187 – 42
n-Butane – 138 0
n-Pentane – 130 36 0.626
n-Hexane – 95 69 0.659
n-Heptane – 90.5 98 0.684
n-Octane – 57 126 0.703
n-Nonane – 54 151 0.718
n-Decane – 30 174 0.73
n-Undecane – 26 196 0.74
n-Dodecane – 10 216 0.749
Isobutane – 159 – 12
Isopentane – 160 28 0.62
Neopentane – 17 9.5
Isohexane – 154 60 0.654
3-Methylpentane – 118 63 0.676
2,2-Dimethylbutane – 98 50 0.649
2,3-Dimethylbutane – 129 58 0.668

Heat of Combustion of Alkanes :

M olar Heat of
No. of C atoms Name of Alkane
Combustion (Kj / M ole)
1 m ethane 890
2 ethane 1560
3 propane 2200
4 butane 2859
5 pentane 3510
6 hexane 4141
7 heptane 4817
8 octane 5450

Heat of Combustion of Cycloalkanes :

Heat of combustion Heat of combustion

Ring size Ring size
per CH2, kcal/mol per CH2, kcal/mol
3 166.6 10 158.6
4 164.0 11 158.4
5 158.7 12 157.6
6 157.4 13 157.8
7 158.3 14 157.4
8 158.6 15 157.5
9 158.8 17 157.2

7
Chemi cal React i ons of Al kanes :
1. Halogenation :
h
RH + X2   RX + HX
Reactivity : X2 : F2 > Cl2 > Br2 > I2
Reactivity of H : 3° > 2° > 1° > CH3 – H
h
e.g. CH3 – CH3 + Cl2 
 CH3 – CH2Cl + HCl
Br
|
h
CH3 – CH2 – CH3 + Br2  CH3  CH  CH3

Cl
|
h
CH3 – CH2 – CH3 + Cl2  CH3  CH  CH3  HCl + CH3 CH2 CH2Cl
( 55%) ( 45%)

2. Nitration : Alkanes are reactive toward nitration but one H is substituted by – NO2 at high
temperature.
400  500C
CH4 + HNO3    
 CH3.NO2 + H2O
400  500C
CH3 – CH2 – CH3 + HNO3    
 CH3 – CH2 – CH2 – NO2

+ CH3  CH  CH3 + CH3CH2 – NO2 + CH3 – NO2

|
NO 2
With higher alkanes due to oxidative nature of HNO3 C– C bond dissociates.

3. Sulphonation : Lower alkanes are not easily sulphonated but hexane & higher members are
sulphonated on heating with oleum (conc. H2SO4 + SO3) at 400°C
400C
C6H14 + H2SO4   C6H13SO3H + H2O

4. Reaction with steam :

CH4 + H2O     CO  3H2

Ni, 1273 K
water gas

5. Isomerisation :

CH3CH2CH2CH3      
 CH3  CH  CH3
Anhyd. AlCl / HCl
3

300C
|
CH3
Isobu tan e

CH3
|
   
    CH3
AlCl3 / HCl
CH3 – (CH2)3 – CH3 300C
CH3 C
|
CH3
Neopentane

8
6. Alkylation : Isoalkanes add to isoalkenes in presence of conc. H2SO4 or HF to give higher
branched alkane

CH3 CH3
| |
CH3  C  H + H C  C  CH     
conc. H2SO4 CH3  C  CH2  CH  CH3
2 3
| | | |
CH3 CH CH3 CH3
3
Isobu tane Isobutene Isooc tan e

7. Aromatisation :
Alkanes containing 6 or more number of C atoms are oxidised (dehydrogenate & cyclised) in
presence of oxidising agent at higher temp. and form benzene derivatives.

CrO  Al O
CH3 – (CH2)4 – CH3    
3 2 3

600C
+ 4H2

CrO  Al O
CH3 – (CH2)5 – CH3  
3
 
2 5

600C

CH3(CH2)6CH3  +

CH3
|
CH3  (CH2 ) 4  CH  CH3 

CH3
|
CH3  (CH2 )3  CH  CH2  CH3 

8. Combustion :
 3n  1 
CnH2n+2 +   O     nCO2 + (n + 1) H2O (Hcombustion = -ve)
combustion
 2  2 
exothermic reaction
 y
CxHy +  x   O2     xCO2 +
combustion y
 
HO
4  2 2

C5H12 + 8O2     5CO2 + 6H2O

combustion


Heat of combustion : Amount of heat i.e. liberated when 1 mole of hydrocarbon is completely
burnt into CO2 & H2O.

9
Heat of combustion as a measure of stability of alkane :
Combustion is used as a measurment of stability.
More branched alkanes are more stable and have lower heat of combustion.

CH3
|
e.g. CH3 – CH2 – CH2 – CH3 CH3  C  CH3
|
I H
II
stability : II > I
Hcomb. : I > II

More branched alkane has more no. of primary C – H bonds. (therefore it has more bond energy).
Homolouges : Higher homologes have higher heat of combustion.
Isomers : Branched isomer has lower heat of combustion.
Cyclo-alkanes : More strained ring has higher heat of combustion per – CH2 – unit.

Alkenes & cyclo-alkanes : Alkenes have higher heat of combustion.

e.g. 1. CH4 < C2H6 < C3H8

C C
| |
2. C – C – C – C – C > C  C  C  C > C  C  C
|
C

3. > > > (Hcomb. per ‘CH2’ unit)

Octane Number : It is a scale of fuel efficiency when the fuel burns during combustion, more
branched alkanes have lower knocking (cracking sound). so are better fuels. On commercial scale
iso-octane has been alotted a rating i.e. octane no. 100 & n-heptane - ‘0’

C
|
CCCCC
| | octane number = 100
C C
C–C–C–C–C–C–C octane number = 0

If the octane no. of a fuel is 80, it means that the efficiency of the fuel is equivalent to the efficiency
of mixture of 80% isoctane and 20% n-heptane.

9. Pyrolysis / Cracking

CH3 – CH2 – CH3 CH3CH3 + CH3CH = CH2 + CH2 = CH2+ CH4 + H2

Higher alkanes are heated in absence of air so these break down into smaller alkanes which are
better fuel. Mixture of products contains all lower alkanes, all alkenes & hydrogens.

1 0
Part - A
1. The reactivity order of photochemical monohalogenation of following alkanes is –
CH3 CH3 CH3
| | |
(1) CH4 (2) C2H6 (3) H3 C  C  CH3 (4) CH3  C  C  CH3
| | |
CH3 CH3 CH3
(A) 1 > 2 > 3 > 4 (B) 2 > 1 > 3 > 4 (C) 4 > 3 > 2 > 1 (D) 2 > 3 > 1 > 4

2. Which of the following reaction has zero activation energy –

(A) CH 4  Cl  CH 3  H  Cl (B) Cl  Cl Cl   Cl 
(C) CH 3  CH 3 CH 3  CH 3 (D) CH 3  Cl  Cl CH 3  Cl + Cl 

3. Photochemical fluorination is explosive while iodination is too slow to occur. The reason for this is
(A) Bond dissociation energy of I2 is minimum
(B) Formation of CH3 – F is most exothermic
(C) Formation of H – F is most exothermic while formation of H – I is endothermic
(D) F2 has lower bond dissociation energy than Cl2 or Br2

4. Which statement is incorrect about free radical halogenation of alkanes –

(A) The number of product molecules formed by one photon is very high
(B) If O2 is added, initially the rate of reaction decreases, then it increases
(C) Inhibitors combine with free radical and terminate the chain reaction
(D) presence of C 6H5  CO  OC  C 6H5 inhibits the free radical reaction.
|| ||
O O

5. Which statement is correct about photochemical bromination of Butane

Br2 , h
CH3 – CH2 – CH2 – CH3  
(A) 1-Bromobutane and 2-Bromobutanes are formed in equal amounts.
(B) 2-Bromobutane is formed with faster rate than 2-chlorobutane in the other experiment of chlo-
rination.
(C) The major product is an equimolar mixture of two compounds
(D) Homolysis of C – H bond has lower activation energy than homolysis of Br – Br bond.

6. Which of the following is not the chain propagation step in the chlorination of an alkane
(A) R • + SO2Cl2  RCl + •SO2Cl (B) •SO2Cl SO2 + Cl•
(C) Cl + R – H
•  R + H – Cl (D) R' OOR + 2RH
• 2R'OH + 2R•

7. An alkane can not be chlorinated by using the following reagent/s –

(A) Cl2/h (B) SO2Cl2 (C) t–Bu–O–Cl (D) HCl

8. Which of the following is/are endothermic reactions –

(A) Combustion of CH4 (B) Decomposition of H2O
(C) Dehydrogenation of ethane to ethene (D) Conversion of graphite to diamond
9. The correct order of heat of combustion of the following hydrocarbons is :
(1) Pent-1-ene (2) n-Pentane (3) neopentane (4) isopentane
(A) 1>2>4>3 (B) 2>4>3>1 (C) 1>2>3>4 (D) 4>3>2>1

1 1
Part - B
1. Allot IUPAC nomenclature to the following compounds :

(a) (b) (c)

2. Arrange the following in decreasing order of :

(i) Reactivity towards Cl2 / h
(A) CH4 (B) CH3 – CH3
CH3
|
(C) CH3 – CH2 – CH3 (D) CH3  CH  CH3

(ii) Relative reactivity in photochemical halogenation :

CH3
|
(A) CH3 – CH2 – CH2 – CH2 – CH3 (B) CH3  CH  CH2  CH3

CH3
|
(C) CH3  C  CH3 (D) CH3 – CH3
|
CH3
(iiii) The reactivity of following free radicals :
 
(A) C H3 (B) C H2 – CH3
 
(C) (CH3)2 C H (D) (CH3)3 C
(iv) The stability of following free radicals :

(A) (B) (C) (D)

(v) Heat of combustion :

CH3
|
(A) (B) (C) CH3 – CH2 – CH2 – CH3 (D) CH 3  CH  CH3

(vi) Reactivity of X2 :
X
(CH3)3CH 
  ;
2

(A) Br2 (B) Cl2 (C) F2 (D) I2

3. Predict the proportions of isomeric products from chlorination at room temperature

(in presence of light) of :
(a) propane (b) isobutane (c) 2,3–dimethylbutane

(d) n-pentane (e) isopentane (f) 2, 2, 3-trimethylbutane

(g) 2, 2, 4-trimethylpentane.

1 2
4. Write major organic products for the following reactions :

Sec-butylbromide  H  J 2 

  K
Li
CuI 5 CHI
(a)

  
LiAlH
4
(b)

   
Electrolysis
(c)

NaOH  CaO
   
(d) 

+ Na  
ether
(e)

+ D2 

Pt
(f)

5. Complete the following reactions by writing monohalogenation products.

Br / h
(i) 2 

Br / h
(ii) 2 

Br / h
(iii) 2 

CH3
|
(iv) CH3  C  H  CCl4 2  
R O
2

|
CH3
h
(v) (CH3)4C + Cl2 


h
(vi) + Br2 

h
(vii) + Br2 

1 3
6. Identify X, Y, Z and W in the following reaction
H2 / Ni Br / h
X, Y, Z (C 4H8 )   2   W
Isomer (1) ( 2)

7. For the given reaction :

CH3 CH3
| |
Br / h
CH3  C  CH2  CH  CH3 2  
|
CH3

(a) Write the number of possible monobromo products. (all isomers)

(b) Arrange all the monobromo products in decreasing order of rate of their formation.
(c) Arrange in decreasing order of % yield of monobromo products.
(d) How many products are optically active ? (all isomers)

8. Identify the unknown compounds in the following sequence of reaction .

9. An alkane with the formula C6H14 can be synthesized by treating (in separate reactions) five
different alkyl chlorides (C6H13Cl) with zinc and aqueous acid. Give the structure of the alkane and
the structures of the alkyl chlorides.

10. An alkane with the formula C6H14 can be prepared by reduction (with Zn and HCl) of only two alkyl
chlorides (C6H13Cl) and by the hydrogenation of only two alkenes (C6H12). Write the structure of this
alkane, give its IUPAC name, and show the reactions.

11. Ignoring compound with double bonds, write structural formulas and give names for all of the
isomers withthe formula C5H10.

12. Write product with proper mechanism for the following reaction
SO Cl  R O
CH3 – CH2 – CH3  
2

2

2 2

1 4
 Answers
EXERCISE
Part - A
1. C 2. C 3. C 4. D
5. C 6. D 7. D 8. B, C, D 9. B

Part - B
1. (a) 2,5–Dimethyl–4,4–dipropylheptane
(b) 4,4–Diisobutyl–2,6–dimethylheptane
or 2,6–Dimethyl–4,4–bis(2–methylpropyl)heptane
(c) 2–Bromo–4–chloro–3–ethyl–3–isopropylpentane

2. (i) D > C > B > A (ii) B > A > C > D (iii) A > B > C > D
(iv) D > A > C > B (v) C > D > A > B (vi) C > B > A > D
3. (a) CH3 – CH2 – CH2 – Cl (44%) , CH3  CH  CH3 (56%)
|
Cl

CH3 CH3
| |
(b) CH3  CH  CH2  Cl (64%) , CH3  C  CH3 (36%)
|
Cl

CH3 CH3 CH3 CH3

| | | |
(c) CH3  CH  CH  CH2  Cl (55%) , CH3  C  CH  CH3 (45%)
|
Cl

(d) CH3 – CH2 – CH2 – CH2 – CH2 – Cl (21%) , CH3  CH2  CH2  CH  CH3 (53%)
|
Cl
CH3  CH2  CH  CH2  CH3 (26%) ,
|
Cl

CH3 CH3
| |
(e) Cl  CH2  CH  CH2  CH3 (28%) , CH3  C  CH2  CH3 (23%)
|
Cl

CH3 CH3
| |
CH3  CH  CH  CH3 (35%) , CH3  C  CH2  CH2  Cl (14%)
|
Cl

CH3CH3 CH3 CH3 CH3 CH3

| | | | | |
(f) Cl  CH2  C  CH  CH3 (45%) , CH3  C  C  CH3 (25%), CH3  C  CH  CH2  Cl (30%)
| | | |
CH3 CH3 C l CH3

1 5
 CH3 CH3 CH3 Cl CH3
| | | | |
(g) CH3  CH  CH2  C  CH2  Cl (33%) , CH3  CH  CH  C  CH3 (28%)
| |
CH3 CH3

CH3 CH3 CH3 CH3

| | | |
CH3  C  CH2  C  CH3 (18%) , CH2  CH  CH2  C  CH3 (22%)
| | | |
Cl CH3 Cl CH3

Li C 2H5
 C 2H5 
|   |
H : CH3  CH  CH2  CH3 J:  |  CuLi K : CH3  CH  CH2  CH3
 CH  CH  
4. (a)
 3 2

CH3
|
(b) (c) (d) Ph  C  CH3
|
H

CH3 CH3
| |
(e) CH3  CH2  CH  CH  CH2  CH3 (f)

CH3
|
5. (i) CH3  C  CH3 (ii) +
|
Br

CH3 CH3
| |
(iii) (iv) CH3  C  Cl  CHCl3 (v) CH3  C  CH2  Cl
| |
CH3 CH3

(vi) (vii)

6. (X) CH3 – CH2 – CH = CH2, (Y)

(Z) , (W) CH3  CH  CH2  CH3

|
Br

7. (a) 6 monobromo products (b) 3° > 2° > 1° (9) > 1° (6)
(c) 3° > 2° > 1° (9) > 1° (6) (d) 4 products are optically active

1 6
8. (R) (S) (T)

(U) (V) (W) CH2 = O

CH3
|
9. Alkane : CH 3  CH  CH2  CH2  CH3
Alkyl chlorides :

CH2Cl CH3
| |
(I) CH3  CH  CH2  CH2  CH3 (II) CH3  C  CH2  CH2  CH3
|
Cl

CH3 CH3
| |
(III) CH3  CH  CH  CH2  CH3 (IV) CH3  CH  CH2  CH  CH3
| |
Cl Cl

CH3
|
(V) CH3  CH  CH2  CH2  CH2Cl

CH3 CH3
| |
10. Alkane : CH3  CH  CH  CH3 2, 3-Dimethylbutane

CH3 CH3 CH3 CH3

| | | |
Alkyl chloride : (I) CH2  CH  CH  CH3 (II) CH3  C  CH  CH3
| |
Cl Cl

CH3 CH3 CH3CH3

| | | |
Alkenes : (I) CH  C  CH  CH (II) CH  C  C  CH
2 3 3 3

11. cyclopentane Methylcyclobutane Ethylcyclopropane

1, 2-Dimethylcyclopropane 1, 1-Dimethylcyclopropane

Cl
|
12. CH3  CH  CH3

1 7