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CAREER POINT .

PRE-MEDICAL
HYDROCARBONS
(ALKANE)

AIPMT Syllabus

1. Alkanes and cycloalkanes.

2. Classification of hydrocarbons.

3. Nomenclature & conformations of alkane and cycloalkane.

Total No. of questions in ALKANE are:

Exercise # 1 …….…………………………….70
Total No. of questions……………………….70

*** Students are advised to solve the questions of exercises in the same sequence or as
directed by the faculty members.

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Index : Preparing your own list of Important/Difficult Questions

Instruction to fill

(A) Write down the Question Number you are unable to solve in column A below, by Pen.
(B) After discussing the Questions written in column A with faculties, strike off them in the
manner so that you can see at the time of Revision also, to solve these questions again.
(C) Write down the Question Number you feel are important or good in the column B.

COLUMN :A COLUMN :B
EXERCISE
NO. Questions I am unable
Good/Important questions
to solve in first attempt

Advantages

1. It is advised to the students that they should prepare a question bank for the revision as it is
very difficult to solve all the questions at the time of revision.

2. Using above index you can prepare and maintain the questions for your revision.

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ALKANE

GENERAL INTRODUCTION :

  These are the hydrocarbons in which Carbon - Carbon contains single bond. (Saturated hydrocarbon).
  These are also called as ‘Paraffins’ (Parum + Affinis i.e. less reactive).
  In alkane if chiral carbon or unsymmetrical carbon is present, then it shows optical isomerism.
  General reagents such as dil. and conc. HCl, dil. and conc.H2SO4, dil. and conc. HNO3, acidic and basic KMnO4
and K2Cr2O7 usually does not react with alkane.
  General formula is CnH2n+2 .(n = 1, 2, 3, 4..............)

  Hybridisation state of carbon is sp3.


  Geometry of carbon is tetrahedral.
  Bond angle is 109º28’.
  Number of bond angle in methane are six, while in ethane are twelve.
H H H
H 4

3 1 2
1 6 5 5
2 3 6
2
H 1 3
4 5 4
H 6 H H H H
Methane Ethane

  C–C bond length is 1.54 Å while C–H bond length is 1.12 Å.


  C–C bond energy is 84 kcal/ mole while C–H bond energy is 98 kcal /mole.
  Alkane shows only chain, position isomerism.
  First three members methane, ethane and propane does not exhibit any isomerism, while butane and pentane
shows only chain isomerism.
H
|
H– C –H CH3–CH3 CH3–CH2–CH3 CH3–CH2–CH2–CH3 CH3–CH –CH3
| |
H CH3
Methane Ethane Propane n-Butane Isobutane
CH3
|
CH3–CH2–CH2–CH2–CH3 CH3–CH –CH2–CH3 CH3–C–CH3 CH3–CH2–CH2–CH2–CH2–CH3
| |
CH3 CH3
n-Pentane IsoPentane NeoPentane n-Hexane
CH3
CH3–CH2–CH–CH2–CH3 CH3–C–CH2–CH3 CH3–CH–CH2–CH2–CH3 CH3–CH–CH–CH3
CH3 CH3 CH3 CH3 CH3

3-Methyl pentane Neohexane Isohexane 2, 3-Dimethyl butane

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 The molecules of alkanes are angular , so carbon chains in these molecules are zig- zag type (not straight) which

may be branched or unbranched as shown below.

(Unbranched) (branched)

PHYSICAL PROPERTIES :

  Alkanes are colourless, odourless and tasteless.

  Physical state:

C1– C4 Gaseous state

C5 – C17 Liquid state (except neo pentane)

C18 & above – Solid like wax

  Alkanes are lighter than water, so it floats over water.

  Solubility : [Like dissolves like]

Alkanes are non-polar or weakly polar compounds so these are soluble in non-polar solvents (benzene, ether,

chloroform, carbontetrachloride etc.) and are insoluble in polar solvents (water etc.).

  Boiling point :

For homologues B.P.  Molecular weight

because Mol. wt.  = Surface area  = Intermolecular Vander wall's interaction  = B.P. 

1
For isomers B.P. 
No. of branches

because Branches  = Spherical shape  = Surface area  = B.P. 

  Melting point :

The melting point of alkanes depends upon molecular weight as well as packing in crystal lattice

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Variation of boiling point and melting point in alkanes

Name Formula Molecular mass B.P. (ºC) M.P. (ºC)


Methane CH4 16 –162 –183
Ethane CH3CH3 30 –88.5 –172
Propane CH3CH2CH3 44 –42 –187
n-Butane CH3(CH2)2CH3 58 0 –138
Isobutane (CH3)2CHCH3 58 –12 –159
n-Pentane CH3(CH2)3CH3 72 36 –130
Isopentane (CH3)2CHCH2CH3 72 28 –160
Neopentane (CH3)4C 72 9.5 –17
n-Hexane CH3(CH2)4CH3 86 69 –95
n-Heptane CH3(CH2)5CH3 100 98 –90.5
n-Octane CH3(CH2)6CH3 114 126 –57
  Graphical representation :

[regular graph] [Irregular or zig-zag graph]


B.P. M.P.

No. of carbon atoms No. of carbon atoms

 M.P. (odd to even) >  M.P. (even to odd)

Ques. Boiling point order ?


(i) CH4 < CH3CH3 < CH3CH2CH3
CH3 CH3
(ii) CH3–C–CH3 < CH3–CH–CH2–CH3 < CH3CH2CH2CH2CH3
CH3
Ques. Melting point order ?
(i) CH3CH2CH3 < CH4 < CH3CH3
CH3 CH3
(ii) CH3–CH–CH2–CH3 < CH3CH2CH2CH2CH3 < CH3–C–CH3
CH3

 Maximum packing due to


symmetrical spherical shape

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CHEMICAL PROPERTIES OF ALKANE :

Halogenation
R–X
X2/h or UV light
(F2 > Cl2> Br2 > I2)

O
Nitration
R–N
HNO3/400ºC O

Sulphonation
R–SO3H
H2S2O7

Reed reaction
R–SO2Cl
SO2 + Cl2/h

SO2Cl2/h
R–Cl

R–H
Isomerisation
or Branched alkane
R–R AlCl3/HCl

Pyrolysis or Cracking
Alkenes + CH4 or C2H6
500º–700ºC

Cr2O3 + Al2O3
Aromatic compound
500ºC

CH2N2/
Higher alkane
step up reaction

O2
CO2 + H2O + HC (exothermic)
combustion

O2 / Cu R–CH2OH
Catalytic Mo2O3
R–CHO
Oxidation (AcO)2 Mn
R–COOH

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PREPARATION METHODS OF ALKANE :

NaOH + CaO/
RCOOH
Soda lime

Kolbe's electrolysis
RCOONa

Na / ether
R–X
Wurtz reaction

Zn / Ether
R–X
Frankland's reaction

(i) Li (ii) CuX (iii) R–X


R–X
Corey-House synthesis

R–H
Zn/HCl or LiAlH4
R–X or
Reduction
R–R

HOH or ROH
R–Mg–X
or NH3 or RNH 2

HI / red P / 140ºC
RCOOH or ROH or R–C–R or RCHO
Reduction
O

Zn–Hg/HCl
R–C–R or R–C–H
Clemmenson's reduction
O O

H2N–NH2 / KOH
R–C=O or R–C=O
Wolff Kishner reduction
R H

200–300ºC, H2/Ni
R–CCH or R–CH=CH2
Sabatier Senderen's reaction

SPECIAL POINTS :
  LPG is called as liquefied petroleum gas or kitchen gas which is a mixture of propane and butane.
  CNG (compressed natural Gas) mainly contains CH4.
  A mixture of n-butane and isobutane is called as Calore gas.
  Methane reacts with ozone to make formaldehyde.
  When methane is heated (at about 1500º C) in presence of nickel it makes acetylene.
  Sabetier Senderen's reaction :
Ni/200ºC
CO + 3H2 CH4 + H2O

Ni/200ºC
     CO2 + 3H2 CH4 + 2H2O
  Preparation of synthesis gas :
     CH4 + H2O     CO + 3H2
Ni / 1000º C

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