Chapter 14
Chapter 14
Chapter 14
HYDROCARBONS
Preparation of Alkanes
1. Heating sodium salts of carboxylic acid with soda-lime
Alkane
Methane
Ethane
Alkane R-X + H2
⃗
Pd
R-H + HX
alkyl halide alkane
Methane CH3I + H2
⃗
Pd
CH4 + HI
methyl iodide methane
Pd
Ethane CH3 CH2I + H2
⃗ CH3 CH3 + HI
ethyl iodide ethane
3. Reduction of Alkenes
Alkane R-CH=CH2 + H2 R-CH2-CH3
alkene alkane
Ethane CH2=CH2 + H2 CH3-CH3
ethene ethane
Propane CH3-CH=CH2 + H2 CH3-CH2-CH3
propene propane
Preparation of Alkenes
1. Dehydration of alcohols
(a) By heating with concentrated sulphuric acid at 160 °C
Alkene RCH2CH2OH R-CH = CH2 + H2O
alcohol alkene
Ethene CH3CH2OH CH2 = CH2 + H2O
ethanol ethene
Propene CH3CH2CH2OH CH3CH = CH2 + H2O
propanol propene
(b) By passing the alcohol vapour over alumina, Al2O3, heated at 350°C
Alkene RCH2CH2OH R-CH = CH2 + H2O
alcohol alkene
Ethene CH3CH2OH CH2=CH2 + H2O
ethanol ethene
Propene CH3CH2CH2OH CH3CH=CH2 + H2O
propanol propene
2. Dehydrohalogenation of alkyl halides
Alkene RCH2CH2X + KOH RCH = CH2 + KX + H2O
RCHXCH3 + KOH RCH = CH2 + KX + H2O
alkyl halide alkene
Ethene CH3CH2 Cl + KOH CH2 = CH2 + KCl + H2O
ethyl chloride ethene
Propene CH3CH2CH2Cl + KOH CH3CH = CH2 + KCl + H2O
n-propyl chloride propene
CH3CHClCH3 + KOH CH3CH = CH2 + KCl + H2O
iso-propyl chloride propene
Preparation of Alkynes
1. Hydrolysis of calcium carbide
CaC2 + 2H2O Ca(OH)2 + CH ≡ CH
calcium carbide ethyne
2. Dehydrohalogenation of ethene dibromide or ethylidene chloride
CH2BrCH2Br + 2KOH CH ¿
CH + 2KBr + 2H2O
chloroform
4. Addition of O3 and CH2 = CH2 + O3
ethene ozonide
decomposition of ethene H2O, Zn dust
ozonide (ozonolysis) H2C=O + H2O2
methanal
5. Addition of hydroxyl CH2 = CH2 + H2O+ [O] CH2OHCH2OH
group (Hydroxylation) ethene ethene glycol
(colourless)
Markownikoff's rule
When an unsymmetrical addendum (HX) adds on to an unsymmetrical alkene,
two products are possible; but that product where the negative part of the addendum
adds on to the carbon with the least number of hydrogen atoms is the major product.
CH3-CH = CH2 + HX CH3CHX-CH3 + CH3CH2-CH2X
propene addendum iso-propyl halide n-propyl halide
(unsymmetrical) (unsymmetrical) (major) (minor)
II. Alkane (single bond rsm;omyg) ESifh Alkyne (Triple bond ygNyD;
triple bonded carbon atom wGif hydrogen atom yg) compound
rsm;udkcGJjcm;jcif;
Br2 solution in ethanol oHk;ícGJ Edkifonf/ Alkyne u"mwfjyKNyD; Br2 \
ta&mifudk azsmuf Edkifonf/ alkane rSm ta&mifrazsmufEdkifyg/
tu,fí Alkyne wGif triple bond ygNyD; triple bonded carbon atom wGif
hydrogen atom vnf;yg&Sd vQif ammoniacal solution of copper (I) chloride
(or) silver oxide oHk;ívnf;cGJjcm;Edkifonf/ Alkane onf xdk solution
rsm;ESifh "mwfrjyKEdkifí rnfonfh tenfrQ rusyg/ Triple bonded carbon
atom wGif hydrogen atom yg alkyne uom"mwfjyKí tenfrsm;usrnf/
Example (2) How would you distinguish between the following pairs of
compounds?
(a) ethane and ethyne (acetylene) (2010) (Try yourself)
(b) propane and propyne (methylacetylene) (2009)
CH3CH2CH3 + Cu2Cl2 + NH3 → No reacation
propane (No ppt)
CH3-C ≡ CH + ½Cu2Cl2 + NH3 → CH3-C ≡ C Cu↓ + NH4Cl
propyne methyl copper acetylide (red ppt)
(c) n-butane and 1-butyne (2011) (Try yourself using either method)
(d) n-butane and 2-butyne (Try yourself using Br2 solution in ethanol)
III. Alkene (double bond yg) ESifh Alkyne (triple bond ygNyD; triple bonded
carbon atom wGif hydrogen atom &Sdaom) compound rsm;udk
cGJjcm;jcif;
xkd compound (2) rsdK;vHk; Br2 solution ESifh "mwfjyKEdkifí Br2
solution oHk;NyD; cGJjcm;í r&Edkifyg/ Ammoniacal solution of copper
(I) chloride (or) silver oxide oHk;ícGJ&rnf/ Alkane rsm;u "mwfrjyKí
tenfrus? Alkyne rsm;om "mwfjyKEdkifí tenfusonfudk awGU&rnf/
Example (3) How would you distinguish between the following pairs of
compounds?
(a) ethene (ethylene) and ethyne (acetylene) (2002,03,04,08,09,11)
CH2 = CH2 + Cu2Cl2 + NH3 → No reaction
ethene (No ppt)
CH ≡ CH + Cu2Cl2 + 2NH3 → C-Cu ≡ C-Cu↓ + 2NH4Cl
ethyne dicopper acetylide (red ppt)
IV. Alkyne &Sd triple bonded carbon atom wGif hydrogen atom &Sdaom
compound ESifh hydrogen atom r&Sdaom alkyne compound
rsm;udkcGJjcm;jcif;
Alkyne wdkY\ triple bonded carbon wGif&Sd hydrogen atom udk metal
atom jzifh tpm;xdk;Edkifonf/ xdkYaMumifh ammoniacal solution of
copper (I) chloride (or) silver oxide ESifh "mwfjyKEdkifNyD; Cu (or) Ag
tpm;xdk;0ifa&mufaeaom metallic acetylide tenfrsm;usvmrnf/ Triple
bonded carbon wGif hydrogen atom r&Sdaom alkyne wdkYudk metal atom
u tpm;rxdk;Edkifí tenfrusEdkifyg/
Example (4) How would you distinguish between the following pairs of
compounds?
(a) ethyne (acetylene) and 2-butyne (dimethyl acetylene)
CH ≡ CH + Cu2Cl2 + 2NH3 → C-Cu ≡ C-Cu ↓ + 2NH4Cl
ethyne dicopper acetylide (red
ppt)
Manufacture of ethanol
(a) From petroleum refinery products
(i) When hydrocarbons of very high molecular weight are heated at 520°C under
12 atm pressure, they break down to give alkanes (C5H12 to C9H20) and
ethene.
(CH3CH2)2SO4 + 2H2O
⃗
Δ
2CH3CH2OH + H2SO4
ethanol
(iv) Ethanol formed is fractionally distilled.
(b) Fermentation method
n malt n
(i) (C6H10O5)n + 2 HO
(diatase) 2C H O
2 12 22 11
starch maltose
(ii) C12H22O11 + H2O 2 C6H12O6
maltose glucose
(iii) C6H12O6 2 CH3CH2OH + 2CO2
↑
glucose ethanol
(iv) Ethanol obtained (11%) is fractionally distilled to yield the rectified spirit
(95 % ethanol).
Chemical properties of alcohols
1. Reaction with metallic sodium
CH3CH2OH + Na
⃗ CH CH ONa + 1/ H
3 2 2 2
CH3CH2OH + H2SO4
⃗
100∘ C
CH3CH2SO4H + H2O
ethanol ethyl hydrogensulphate
4. Butene has 3 isomers. Write their structural formulae and name them.
10. Complete the following equations and name the organic compounds.
(a) CH3-CH2CH2COONa + NaOH ?
⃗
(b) CH2 = CHBr + HBr ?
(c) RCH2CH2OH ?
Ans: (a) CH3CH2CH2COONa + NaOH CH3CH2CH3 + Na2CO3
sodium butanoate propane
(b),(c) See in respective reaction
11. (a) By heating a mixture of sodium propionate and soda-lime, a gas “A” is
evolved. What is gas “A”? Write down the equation.
(b) Gas “A” can also be formed by hydrogenation of an alkene using a nickel
catalyst at 300 ºC. Name the alkene. Write down the equation.
(c) Is the gas “A” saturated or unsaturated hydrocarbon? Write down the
general formula.
Ans: (a) Gas A is ethane.
CH2=CH2 + H2 CH3-CH3
ethene ethane
(c) The gas “A” is saturated hydrocarbon. It's general formula is C2H4.