Unit 14- Hydrocarbons
Organic compounds having only carbon and hydrogen
Classification of Hydrocarbons
Hydrocarbons
Acyclic or open- Cyclic or closed-
chain compounds chain compounds
Alkanes Alkenes Alkynes Alicyclic Aromatic
CnH2n+2 CnH2n CnH2n-2 hydrocarbons hydrocarbons
Aliphatic Hydrocarbons
Alkanes: Open chain singly bonded hydrocarbons are
called alkanes. They are represented by a molecular
formula of CnH2n+2. Examples: CH4 (methane), CH3CH3
(ethane).
Alkenes: Open chain doubly bonded hydrocarbons are
called alkenes. They are represented by a molecular
formula of CnH2n. Examples: CH2=CH2 (ethene).
Alkynes: Open chain triply bonded hydrocarbons are
called alkynes. They are represented by a molecular
formula of CnH2n-2. Examples: CH ≡ CH (ethyne).
Unit 14.1- Saturated
Hydrocarbons (alkanes)
Preparation of alkanes:
1. Catalytic hydrogenation of alkene and alkyne
2. Wurtz reaction
3. From Grignard’s reagent
4. Catalytic reduction of haloalkanes
5. Sodalime Decarboxylation
Preparation of alkanes:
1. Catalytic hydrogenation of alkene and alkyne
Alkenes and alkynes react with Hydrogen in presence of nickel,
platinum or palladium catalyst at high temperature to form
corresponding alkanes.
H H H H
Ni,Pt or Pd,250−300 °C
H − C = C − H + H2 H−C−C−H
H H
Ethene ethane
H H
Ni,Pt or Pd,250−300 °C
H − C ≡ C − H + H2 H−C−C−H
H H
Ethyne ethane
Unsaturated vegetable oils are converted to saturated vegetable
ghee (Vanaspati Ghee) by catalytic hydrogenation as above.
Preparation of alkanes:
By Wurtz reaction
When alkyl halides are heated with sodium metal in presence of
dry ether as solvent, higher alkanes are obtained. This reaction is
called wurtz reaction.
𝑑𝑟𝑦 𝑒𝑡ℎ𝑒𝑟,∆
R-X + 2Na + X-R 𝑅 − 𝑅 + 2𝑁𝑎𝑋
Alkylhalide
Examples:
𝑑𝑟𝑦 𝑒𝑡ℎ𝑒𝑟,∆
CH3 -I + 2Na + I- CH3 CH3 − CH3 + 2𝑁𝑎I
Iodomethane Ethane
Advantage of Wurtz reaction:
• Number of carbon atoms gets doubled by this process so it is
useful for step-up process.
Limitations of Wurtz reaction:
• This method is not suitable for preparation of unsymmetrical
alkanes.
• Methane can’t be prepared by this method.
Note: Ether used in this process must be dry otherwise Na reacts
with water or alcohol giving.
2Na + 2H2 O → 2NaOH + H2
2Na + 2𝑅𝑂𝐻 → 2RONa + H2
Preparation of alkanes:
Using Grignard reagent
Alkyl halide reacts with magnesium metal in anhydrous ether to
form alkyl magnesium halide which is commonly called Grignard
reagent.
dry ether,inert atm.
RX + Mg RMgX (Grignard reagent)
RMgX + H2 O → R − H + Mg OH I
Grignard reagents react readily with water to give alkane. This
reaction is called hydrolysis of Grignard reagent.
Example RMgX + H2 O → RH + Mg OH X
dry ether,inert atm.
CH3 I + Mg CH3 MgI
CH3 MgI + H2 O → CH4 + Mg OH I
Preparation of alkanes:
Catalytic reduction of haloalkanes
Alkanes can be prepared by catalytic reduction of haloalkane in
presence of hydrogen and Ni, Pt or Pd catalyst.
𝑁𝑖,∆
R − X + H2 R − H + HX
𝑁𝑖,∆
CH3 CH2 I + H2 CH3 CH3 + HI
Preparation of alkanes:
Sodalime Decarboxylation
Sodalime is mixture of solid NaOH and quick lime (CaO) in the
ratio 3:1.
When sodium salt of carboxylic acid (sodium carboxylate) is
heated with sodalime, CO2 is removed and alkane is obtained
having one carbon less than that in acid.
NaOH+CaO,∆
R − COONa + NaOH R − H + Na2 CO3
Sodium carboxylate Alkane
Examples:
NaOH+CaO,∆
CH3 COONa + NaOH CH4 + Na2 CO3
NaOH+CaO,∆
CH3 CH2 COONa + NaOH CH3 CH3 + Na2 CO3
This reaction is laboratory method of preparation of methane and
ethane.
NEB Questions:
1. Write reaction for the preparation of methane from: CH3MgBr,
CH3COONa (Sodium ethanoate), Chloromethane,.
2. Write an example of Wurtz reaction, decarboxylation reaction.
3. What happens when sodium acetate is heated with sodalime?
OR Describe the preparation of ethane in laboratory.
4. What products would you expect when 2-bromopropane is
heated with Na/dry ether.
5. A haloalkane ‘X’ undergoes Wurtz reaction to give 2,3-
dimethylbutane as the major product. Identify ‘X’ and write
chemical reaction. OR
A haloalkane X if heated with sodium metal in presence of dry
ether produces 2,3 dimethyl butane as major product. Identify X
with chemical reaction.
6. Convert methane to ethane.
Chemical properties:
A. Substitution reactions
1. Halogenation
2. Nitration
3. Sulphonation
B. Oxidation of ethane
1. Complete Oxidation or Combustion
2. Catalytic oxidation
Chemical properties: Substitution reactions
Halogenation
Halogenation is defined as the reaction which involves the
substitution of one or more hydrogen atoms of alkanes by
halogen atoms in presence of ultraviolet (UV) light or at high
temperature.
Examples:
𝑈𝑉 𝑙𝑖𝑔ℎ𝑡 𝑜𝑟 ∆
R-H + Cl2 R − Cl + HCl
∆
CH4 +Cl2 → CH3 − Cl + HCl
∆
CH3 − Cl + Cl2 → CH2 Cl2 + HCl
∆
CH2 Cl2 + Cl2 → CHCl3 + HCl
∆
CHCl3 + Cl2 → CCl4 + HCl
Chemical properties: Substitution reactions
Nitration:
When alkane reacts with nitric acid at high temperature one
hydrogen of alkane is substituted by - NO2 group to give
nitroalkane called nitration of alkane.
Examples:
∆
R-H + HNO3 → R − NO2 + H2 O
Nitroalkane
∆
CH3 − H + HO − NO2 → CH3 − NO2 + H2 O
nitromethane
Chemical properties: (Substitution reaction)
Sulphonation
Branched chain and higher n-alkanes with six or more carbon atoms
undergo sulphonation with fuming sulphuric acid (oleum) to give
alkanesulphonic acids.
Examples:
∆, SO3
R-H + H2 SO4 R − SO3 H + H2 O
fuming sulphuric acid alkane sulphonic acid
∆, SO3
C6 H14 + H2 SO4 C6 H13 − SO3 H + H2 O
hexane sulphonic acid
Chemical properties:
Oxidation of ethane
Complete Oxidation or Combustion
Alkane burns completely to give carbondioxide, water and
releasing large amount of heat.
∆
CH3 CH3 + 3.5O2 → 2CO2 + 3H2 O + heat
Catalytic oxidation
Alkane (3° or tert) gets oxidized by oxidizing agent
(alkaline KMnO4) into alcohol.
Uses:
1. Lower alkanes in natural gas and petroleum are
used as fuels.
2. Low boiling liquid e.g. hexane are used as solvents.
3. Higher alkanes are used as lubricants.
4. Used for making explosive, rubber, synthetic
organic compound etc.
Questions:
1. An alkane A with mol. Formula C4H10 give a
mixture of 1-chloro-2-methylpropane and 2-chloro-
2-methylpropane on chlorination. Identify A and
write its structural isomer.
2. An alkane A with mol. Formula C5H12 give a
mixture of three chloroalkane on monochlorination.
Identify A.
Unit 14.2- Unsaturated
Hydrocarbons (Alkenes)
Preparation of Alkene:
Dehydration of alcohol
𝐶𝑜𝑛𝑐.𝐻2𝑆𝑂4,160−170°𝐶
C2 H5 OH H2 –C=C –H2 + H2 O
Or Alumina, 350°𝐶
Dehydrohalogenation
Catalytic hydrogenation of alkyne
Pd /BaSO4,,Partially poisoned
H − C ≡ C − H + H2 H − CH = CH − H
Ethyne (𝐿𝑖𝑛𝑑𝑙𝑎𝑟 𝑐𝑎𝑡𝑎𝑙𝑦𝑠𝑡) ethene
Preparation of Alkene:
Dehydration of alcohol
Alkene can be obtained by dehydrating alcohol with excess of
concentrated sulphuric or phosphoric acid (dehydrating agent )
OR by passing vapour alcohol over heated alumina(Al2O3). This
process is called dehydration of alcohol.
𝐴𝑐𝑖𝑑,∆
–C–C– –C=C – + H2 O
Examples:
𝐶𝑜𝑛𝑐.𝐻2𝑆𝑂4,160−170°𝐶
H– C – C –H H2 –C=C –H2 + H2 O
Ethanol Ethene- Lab Prepn Method
Alumina, 350°𝐶
H– C – C –H H2 –C=C –H2 + H2 O
Preparation of Alkene:
Dehydrohalogenation
When monohaloalkane (alkyl halide) is boiled with alcoholic
solution of caustic alkali, an alkene is formed with the elimination of
hydrogen and halogen. This reaction is called dehydrohalogenation.
𝐵𝑜𝑖𝑙,∆
– C – C – +KOH –C=C – +KI + H2 O
Examples:
𝐵𝑜𝑖𝑙,∆
H– C – C –H+KOH H2 –C=C –H2 +KI+ H2 O
Preparation from alkenes:
Catalytic hydrogenation of alkyne
Alkynes react with Hydrogen in presence of palladium catalyst
deposited over BaSO4 which is partially poisoned by sulphur or
quinoline (Lindlar catalyst) at high temperature to form
corresponding alkenes. This process is called catalytic
hydrogenation.
H H
Pd /BaSO4,,Partially poisoned
H − C ≡ C − H + H2 H−C=C−H
Ethyne ethene
(𝐿𝑖𝑛𝑑𝑙𝑎𝑟 𝑐𝑎𝑡𝑎𝑙𝑦𝑠𝑡)
Properties of Alkene: Markovniko’s rule
Addition reaction with HX
Anti-Markovniko’s rule
Addition of H2O
Addition of H2SO4 indirect hydration
𝐻2𝑂
CH3- CH2OH + H2SO4
Addition of Ozone (Ozonolysis)
Chemical properties of Alkene:
Addition reaction with HX
When dry gas of hydrogen halide is passed into alkene, alkyl halide
is formed which is called hydrohalogenation.
Note: Aq. HX is not used to avoid hydrolysis.
H H H H
H-C = C-H + HI → H – C – C –H
H I
CH3-CH = CH-CH3 + HCl → CH3-CH - CH-CH3
H Cl
Unsymmetrical Alkene and Unsymmetrical reagent:
Alkene which can not be divided into two equal halves are called
unsymmetrical organic compounds.
Example:
CH2 = CH2 CH3-CH = CH2
Symmetrical Unsymmetrical
Reagent which can not be divided into two equal halves are called
unsymmetrical reagent.
H-H, Br-Br H-Cl, H-OH
Symmetrical Unsymmetrical
Markovniko’s Rule for Addition
When and unsymmetrical reagent is added to unsymmetrical
unsaturated hydrocarbon, negative part of the reagent is added to the
unsaturated carbon having less number of hydrogen. This is called
Markovniko’s rule.
Example:
CH3-CH = CH2 + H-Cl → CH3-CH - CH2
Cl H
CH3-CH = CH2 + H-Cl → CH3-CH - CH2
H Cl
Mechanism involves electrophilic addition of
H+ into double bond to form carbocation.
Anti-Markovniko’s Rule for Addition (Peroxide Effect)
When and HBr is added to unsymmetrical unsaturated hydrocarbon
in presence of traces of organic peroxide(R-O-O-R), bromine is
added to the unsaturated carbon having more number of hydrogen.
This is called Anti-Markovniko’s rule or Peroxide effect.
Example:
organic peroxide
CH3-CH = CH2 + H-Br CH3-CH - CH2
H Br
organic peroxide
CH3-CH = CH2 + H-Br CH3-CH - CH2
Br H
Mechanism involves free radical addition of
Br· into double bond to form carbocation.
Chemical properties of Alkene:
Addition of H2O
Alkene reacts with water at high temperature and pressure in
presence of phosphoric acid catalyst to give alcohol. This is
direct hydration and it follows Markovnikov’s rule.
Example:
H3𝑃𝑂4,240°𝐶
CH3-CH = CH2 + H-OH CH3-CH - CH2
OH H
Chemical properties of Alkene:
Addition of H2SO4
Alkene reacts with cold and concentrated sulphuric acid to form
alkyl hydrogen sulphate which on heating with water gives
alcohol. So it is called indirect hydration.
Example:
CH3-CH = CH2 + H-OSO3H → H3-CH - CH2
OSO3H H
𝐻2𝑂
CH3-CH - CH3 + H-OH CH3-CH - CH2 + H2SO4
OSO3H OH H
Chemical properties of Alkene:
Addition of Ozone (Ozonolysis)
When ozone is passed through alkene dissolved in CCl4,
addition product called ozonide is formed which on distillation
with water in presence of Zn dust gives aldehydes or ketones or
their mixture.
Zn dust here acts as reducing agent and also absorbs H2O2
which otherwise oxidizes aldehyde into carboxylic acid.
+ H2O2
distillation
Its is used to locate position of double bond, and also to prepare
aldehydes and ketones.
Questions:
1. Write an example of peroxide effect.
2. Write an example of Markonikov’s rule.
𝐴𝑙𝑐.𝐾𝑂𝐻,∆ 𝑜𝑧𝑜𝑛𝑜𝑙𝑦𝑠𝑖𝑠,∆
3. Identify A and B in: H3 C − CH2 − Br A B.
𝐴𝑙𝑐.𝐾𝑂𝐻,∆ 𝐻𝐵𝑟
4. Identify A and B in:H3 C − CH2 CH2 − 𝐵𝑟 A B.
𝐻𝐵𝑟 𝑁𝑎,∆,𝑑𝑟𝑦 𝑒𝑡ℎ𝑒𝑟
5. Identify A and B in:H3 C − C𝐻 = CH2 A B.
ozonolysis
6. Identify product:2 − Methylbut − 2 − ene product.
7. Write an example of wurtz reaction.
8. The ozonolysis of a compound gave acetone as the only product.
Identify the compound.
9. How is ethene prepared in Lab?
Unit 14.3- Unsaturated
Hydrocarbons (Alkynes)
Preparation of Alkyne:
From Carbon and Hydrogen
Dehydrohalogenation (From 1,2 dihaloalkane or vicinal dihalide)
Chloroform/ iodoform
Lab Preparation (From calcium carbide)
CaC2(s) + 2H2 O(l) → H − C ≡ C − H(g) + Ca(OH)2(aq)
Preparation of Alkyne:
From carbon and hydrogen:
Ethyne can be prepared by passing electric spark in the mixture
of C and hydrogen gas.
Preparation of Alkyne:
From 1,2 dihaloalkane
When 1,2-dihaloalkane (alkyl halide) is boiled with alcoholic
solution of caustic alkali, an alkyne is formed with the elimination of
hydrogen halide in two steps. This reaction is called
dehydrohalogenation.
H Br H Br
𝐵𝑜𝑖𝑙,∆ 𝐵𝑜𝑖𝑙,∆
– C – C – +KOH(alc) –C=C – –C ≡ C –
-KI, - H2 O -KI, - H2 O
Br H
If NaNH2 (Sodamide) is used instead of KOH it directly give alkyne
with removal of NaBr and NH3.
Preparation of Alkyne:
Chloroform/ iodoform
When iodoform or chloroform is heated with metallic silver
powder acetylene gas is produced.
Preparation of Alkyne:
Lab Preparation
Ethyne is prepared in Lab by reacting calcium carbide with
water which is a exothermic reaction.
CaC2(s) + 2H2 O(l) → H − C ≡ C − H(g) + Ca(OH)2(aq)
Properties of Alkyne:
Addition of hydrogen
Addition of Hydrogen halide
Addition of water
Acidic Nature of Alkyne
Chemical properties of Alkyne :
Addition reaction with hydrogen
Alkynes react with Hydrogen in presence of nickel, platinum or
palladium catalyst at high temperature to form corresponding
alkanes.
H H
Ni,Pt or Pd,250−300 °C
H − C ≡ C − H + H2 H−C−C−H
H H
Ethyne ethane
Chemical properties of Alkyne:
Addition reaction with HX
When dry gas of hydrogen halide is passed into alkyne,
dichloroethane is formed which is called hydrohalogenation.
Note: Aq. HX is not used to avoid hydrolysis.
H-C ≡ C-H + HCl → H – C = C –H (Chloroethane)
H Cl
H Cl
H-C = C-H + HCl → H-C – C-H
H Cl H Cl
Chloroethane 1,1-Dichloroethane
Chemical properties of Alkyne:
Addition of H2O
Ethyne reacts with water in presence of 1 % HgSO4 and H2SO4 to give
ethanol which is unstable and rearrange to give ethanal.
Example:
1% HgSO4,H2SO4 rearrange
H- C = C-H + H-OH H-C = C-H H3C=C=O
OH H H
Ethyne Unstable Ethanal
Chemical properties of Alkyne:
Acidic Nature of alkyne
Compound Ethyne Ethene Ethane
Hybridization sp sp2 sp3
% of s character 50 33.33 25
Acidic nature decreases→
In alkyne shared electron is pulled more strongly by s orbital
and it have more tendency to lose proton.
Chemical properties of Alkyne:
Acidic Nature-
Test of Unsaturation (Ethene and Ethyne):
Bromine water test
Alkene and alkyne react with bromine solution dissolved in carbon
tetrachloride as a solvent to give dihalide and tetrahalide
respectively. Here the reddish-brown color of bromine is
decolorized.
Test of Unsaturation (Ethene and Ethyne):
Bayer’s test
Ethene is oxidized by Bayer’s reagent (alkaline solution of
KMnO4) to give glycol. This reaction is called Baeyer’s test.
Here, the pink colour of KMnO4 is discharged.
Ethyne is reacted with Baeyer’s reagent to give oxalic acid.
Here, pink color of KMnO4 is discharged.
Comparative studies of Physical properties of alkane, alkene
and alkyne
Properties Alkane Alkene Alkyne
Addition Does not give Most reactive Less reactive
reaction
Physical states Gases (upto C4), Gases (upto C4), Gases (upto C4),
Liquids (C5-C17), Liquids (C5-C18), Liquids (C5-C12),
Higher solids Higher solids Higher solids
Color and Odor Colorless and Colorless and Colourless and
odorless (upto C4), odorless (except odorless except
Colorless with odor ethylene) acetylene
(C5-C17), Higher
members are white
solid with no odor
Volatility More volatile Less volatile Less volatile
M. Pt and B. Pt. Lowest B. Pt. Slightly higher Highest
Kolbe’s Electrolysis methods for the preparation of alkane
Electrolysis of concentrated solution of sodium carboxylates
gives alkane at anode.
Kolbe’s Electrolysis methods for the preparation alkene
Electrolysis of concentrated solution of sodium or potassium
salt of succinic acid gives ethene at anode.
Kolbe’s Electrolysis methods for the preparation alkynes
Electrolysis of concentrated solution of sodium or potassium
salt of maleic or fumaric acid gives ethene at the anode.
Questions:
1. How is acetylene prepared in the lab from calcium carbide? Give
a reaction to detect unsaturation in acetylene.
𝐻2𝑂 𝑎𝑚𝑚𝑜𝑛𝑖𝑐𝑎𝑙 𝐴𝑔𝑁𝑂3
2. Identify A and B in: CaC2 A B.
𝐻2𝑂 ∆,𝑐𝑜𝑛𝑐.𝐻2𝑆𝑂4/𝐻𝑔𝑆𝑂
3. Identify A and B in: CaC2 A B.
𝐻2𝑂 ∆,𝐹𝑒 𝑡𝑢𝑏𝑒
4. Identify A and B in: CaC2 A B.
𝐴𝑔 𝑝𝑜𝑤𝑑𝑒𝑟,∆ 𝐻2,𝑃𝑑,𝐵𝑎𝑆𝑂4
5. Identify A and B in: CHCl3 A B.
𝐻2𝑂 ∆,𝑟𝑒𝑑 ℎ𝑜𝑡 𝑡𝑢𝑏𝑒
6. Identify A and B in:CaC2 A B.
7. Write a chemical test to distinguish ethyne from ethene.
8. How would you convert ethyne into ethene and benzene.
9. Give a chemical reaction to show acidic nature of ethyne.
10.What happens when ethyne reacts with aq. alkaline potassium
permanganate solution?
11.Give suitable reaction for preparation of ethene and ethyne. How
does ethyne react with water and cuprous chloride.
12.How would you convert ethyne into ethane?
Questions:
1. What happens when ethyne is treated with dil. H2SO4 in
presence of HgSO4?
2. Suggest two chemical reactions to show the acidic nature of
acetylene.
3. A compound A (C3H7Br) reacts with alcoholic KOH to form a
compound B. When B is reacted with HBr, two isomeric
compounds (C and D) are obtained. Both C and D on reduction
with LiAlH4 give E. Identify A, B, C , D and E with IUPAC
name and reaction.
4. An unsaturated compound A (C2H4) is reacted with HBr to form
B. When B undergoes the Wurtz reaction, C is formed. Identify
A, B and C with IUPAC name and suitable reactions.
5. Write short notes on: Bayer’s test and Bromine water test.
Questions: (Unit 14: Hydrocarbon-1)
1. The organic compound obtained by electrolysis of fumaric acid is: ethane, ethene,
ethyne, ethanol
2. Write the name of salt of acid which gives ethane from Kolbe’s electrolysis.
3. Write a reaction between 2-chlorobutane and alcoholic solution of KOH.
4. An alkene (A) having two carbon atoms react with broine to give 1,2-dibromoethane.
a. What type of reaction is this?
b. How can you test chemically the compound (A) in the laboratory?
5. In following sequence of reaction[5]
𝑐𝑜𝑛𝑐 𝐻2𝑆𝑂4,170°𝐶 𝐻2,𝑃𝑡 𝐶𝑙2,𝑆𝑢𝑛𝑙𝑖𝑔ℎ𝑡 𝑁𝑎,𝑑𝑟𝑦 𝑒𝑡ℎ𝑒𝑟
Ethanol 𝐴 𝐵 𝐶 D
The compound D has molecular formula C4H10.
a. Identify A,B,C and D and write their IUPAC name
b. Write the name of reaction for conversion of C to D.
6. An unsaturated hydrocarbon B upon treatment with Hydrogen bromide produces
compound C. Compound C reacts with sodium metal in the presence of organic ether
produces compound D of molecular formula C6H14.
a. Give the chemical equations for the conversion of compound B to compound C and
compound C to compound D. [2]
b. Write down the IUPAC name of compound C and D. [2]
c. Give the structural formula of positional isomer of compound C. [1]
7. Draw unsymmetrical alkene with 4 carbon atoms. What happens when the alkene react
with chlorine gas? Draw the structural formula of the product when the unsymmetrical
alkene react with HBr gas.
Questions: (Unit 14: Hydrocarbon-2)
8. A saturated hydrocarbon ‘A’ on chlorination gives compound ‘B’. Compound ‘B’ on
boiling with alc. KOH gives compound ‘C’. Compound ‘C’ on ozonolysis gives
formaldehyde whose aqueous solution is used to preserve the biological specimens.
[2+2+1]
a. Write chemical reactions for the conversion of A to B to C with IUPAC names of each.
b. Also write the reaction to convert C to formaldehyde.
c. What happens when C reacts with Baeyer’s reagent (alkaline KMnO4)?
9. An alkene X undergoes ozonolysis and gives two compounds Y and Z of molecular
formula C3H6O. Y and Z are functional isomer of each other.
a. Write the two-steps chemical equation for the conversion of X and Y and Z. [2]
b. Write the structural formula of Y and Z. Why are they called functional isomers?[3]
c. What happens when hydrogen gas in the presence of nickel catalyst is passed over X?[1]
d. What is the application of ozonolysis in the organic reaction mechanism?[1]
e. How can you proce chemically the compound X is unsaturated? [1]
10. What is the structural formula of the major product when hydrogen bromide reacts with
2-methylbut-2-ene? CH2BrCH(CH3)CH2CH3, (CH3) 2CBrCH2CH3, (CH3)
2CHCHBrCH3, (CH3) 2CHCH2CH2Br
11. Deviation from Markonikov’s rule occur in presence of: Zinc, peroxide, Zn/HgCl, all
12. Ozonolysis of 2-methylbut-2-ene gives: Propanone/ethanal,
Propanone/propanal/Propanal/ethnal. Methanol/Buranone
13. The double bond present in the alkene and its position can be identified by: a) Bromine
water, b) Ammonical AgNO3, c) ozonolysis, d) None of the above
Questions: (Hydrocarbon-3)
14. 1-bromopropane on treatment with sodium and dry ether forms compound A. [2+1+2]
a. What is the name of this reaction? Write the complete reaction.
b. Write the IUPAC name of compound A.
c. Write all the possible isomers of compound A.
1. Complete the reaction sequence with proper reagent.
𝐵 𝐾𝑀𝑛𝑂4/𝑂𝐻−
A→ 𝐻3𝐶 − 𝐶𝐻 = 𝐶𝐻2 𝐶
15. An organic compound A is produced by the dehydrohalogenation of C3H7Br. The
compound A is treated with ozone in the presence of CCl4, compound B and C is formed.
The compound B is reduced in the presence of Zn/Hg/HCl, compound D is obtained.
[3+2+1+2]
a. Write the reaction sequence of the conversion of A to D.
b. Write the IUPAC name of C and D.
c. How can you prove chemically the compound A is unsaturated?
d. How can you convert compound A into 2,3-dimethylbutane?
16. An alkene X undergoes ozonolysis and gives two compounds Y and Z of molecular
formula C2H4O and CH2O respectively.
a. What happens when hydrogen bromide is added to the compound X?
b. How can you prepare compound X from 1-chloropropane?
c. How can you prove chemically the compound X is unsaturated?
d. Convert compound Y into ethane.
e. How can you prepare ethene from Kolbe’s electrolysis?
Questions: (Hydrocarbon-4)
17. An alcohol (A) on heating with conc.H2SO4 at 170 °C (dehydration) gives compound (B)
which on ozonolysis forms the mixture of methanal and ethanal.
a. Identify A and B, and write the complete reaction for the conversion of A into B.
b. Write the ozonolysis reaction of compound B.
c. What happens when compound B reacts with HBr in presence of organic peroxide?
d. What happens when the product formed in question reacts with alc.KOH?
18. An unsaturated hydrocarbon A upon treatment with hydrogen iodide produces compound
B. Compound B undergoes a Wurtz reaction to give 2.3-dimethylbutane as the major
product.
a. Give the chemical equations for the conversion of compound A to compound B and
compound 2,3-dimethylbutane.
b. Write the IUPAC name of compound A nd B.
c. What is the role of dry ether in Wurtz reaction? Also mention the limitation of this
reaction.
19. Alkynes and alkenes are homologous series of unsaturated hydrocarbons. All alkynes
contain a C≡C triple bond.
a. Write structure and name of second member of alkyne.
b. What happens when first member of alkyne is heated with ammonical solution of silver
nitrate solution?
c. What product is formed when second member of alkyne is on ozonolysis?
Questions: (Hydrocarbon-5)
20. An organic compound (X) is obtained by the treatment of calcium carbide with water and it is
unsaturated hydrocarbon. [2+1+2]
a. Convert compound (A) into butane.
b. What happens when compound (A) is passed through red hot copper tube at 400 °C
temperature?
c. How can you prepare compound (A) from Kolbe’s electrolysis?
21. The organic compound A is formed by reacting water with calcium carbide. The compound A is
treated with 42% H2SO4 and 1% HgSO4 to give compound B. The compound A is heated with
Fe-tube to give C with molecular formula (C6H6).. [2+2+1]
a. Write the conversion of A to B.
b. Write the IUPAC name of compound B and C.
c. How can you test the compound A?
22. Converting one organic compound to another organic compound by using one or more other
organic compounds or reagent by a single or multiple steps is called an organic conversion.
What happens when? [2+1+1+1]
a. 2-chloropropane is heated with sodium metal in presence of dry ether. Write the IUPAC name of
the product.
b. Sodium acetate is heated with soda-lime in presence of quicklime.
c. Ethyne is treated with ammonical cuprous chloride.
23. When propene reacts with HBr in the presence of organic peroxide gives major products
opposite to Markovnikov’s rule. Only unsymmetrical reagents are used for Markovnikov’s rule.
[2+2+2+2]
a. Write the complete reaction with major products. State peroxide effect.
b. Why is it found with HBr but not with HCl and HI?
c. What are unsymmetrical reagent? Write example.