HYDROCARBONS

“If the size of your courage is double than the trouble than
your trouble will become a water bubble.”

 Hydrocarbons are compounds of carbon and  LiAlH4 can reduce only 1° and 2° alkyl halides. But 3°
hydrogen. R–X gives elimination product as the major product.
 NaBH4 reduces 2° & 3° R–X only.
Hydrocarbon ii. By Wurtz reaction
R–X + 2Na + X–R dry etherR–R + 2NaX
2 CH3 I NaCH3 – CH3 + 2NaI
Aromatic
Aliphatic  This reaction shows free-radical mechanism.
Eg. Benzene, Naphthalene etc.
 This method is used for preparation of alkanes
Saturated: Eg. Alkene containing even number of carbons.
Unsaturated: Eg. Alkyne  Methane cannot be prepared by this method.
 Tertiary alkyl halides cannot be converted into
Alkanes alkanes by this method because they convert into
alkenes due to elimination.
v Also called paraffins (parum = little; affins = affinity)
v General formula CnH2n+2 Note:
v All bond angles in alkanes are 109.5° with tetrahedral  If in Wurtz reaction, instead of Na; Zn is used, then the
shape/structure. reaction is called Frankland reaction.

Isomerism R–I + Zn + I–R  R–R + ZnI2

v Alkane shows chain, position, optical and C. From carboxylic Acids
conformational isomerism. i. Decarboxylation
Types of Isomerism Starts from C.No. - RCOONa + NaOH + CaO  RH + Na2CO3
Chain 4 - NaOH and CaO(lime) is used in ratio 3:1
Position 6 - Alkane obtained by this method has one carbon
Optical 7 less than the parent acid.
Conformational 2 - Decarboxylation of sodium formate fives H2
Preparation of Alkanes HCOONa + NaOH+ CaO H2 + Na2CO3
A. From unsaturated hydrocarbons iii. Kolbe's Electrolytic Method
R – CH = CH – R’ + H2 Ni R–CH2–CH2–R' - Alkenes with even number of carbons are
obtained at anode.
 Other catalyst used platinum, palladium, Nickel or
P+O2 form alkanes. RCOONa +2H2O R–R+2CO2+2NaOH+ H2
 Platinum and palladium can catalyze the reaction - Electrolysis of HCOONa produces only H2 and
at room temperature but Nickel as a catalyst CO2.
requires higher temperature. D. Reduction
Note: w Alcohol, Aldehydes, Ketones and acids is converted
to alkanes, by heating with HI and red P at 425 K
 Hydrogenation of alkene and alkyne in presence of Ni at
under pressure.
200-300°C is called Sabatier - Senderen's reaction.
R–OH + 2HI Red PR–H+H2O + I2
 Methane can't be obtained by this method.
R–CHO + 2HI Red PR–CH3 + H2O + 2I2
B. From alkyl halides reduction R-COOH + 6HI Red P R–CH3+2H2O + 3I2
i. R–X + 2[H] → R–H + HX E. Corey-House Synthesis
C2H5Cl Zn+HClC2H6 + HCl w It is applicable to both symmethical and
Note: unsymmetrical alkenes
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 w This reaction involves coupling between a lithium Note:
dialkyl copper, R2CuLi and alkyl halide
 Order of reactivity of halogen with alkanes is: F 2 > Cl2 >
R–X LiR – +R'X Ether Br2 > I2
R'–R+ RCu + LiX
 Order of reactivity of hydrogen in alkane with halogen
w Diakyl lithium cuprate is also known as Gilman is: 3°H > 2°H > 1°H
Reagent.
ii. Nitration
F. Hydrolysis of aluminium and Berylium carbide.
R–H + con.HNO3 450°CR–NO2 + H2O
w Methane can be obtained by the hydrolysis of
iii. Sulphonation: Alkanes with six or more carbon
Aluminium carbide and Berylium carbide. These
atoms on heating with fuming sulphuric acid or
are known as methanides.
oleum (con. H2SO4 + SO2) produce sulphonic acids.
Al4C3 + 12H2O ¾® 3CH4 + 4Al(OH)3
C6H13–H+H2SO4 400–500°CC6H13SO3H+H2O
Be2C + 4H2O ¾® CH4 + 2Be (OH)2
- Members lower than hexane cannot be
But CaC2 + 2H2O¾®CaC2 + C2H2+ Ca(OH)2 sulphonated.
Physical Properties B. Oxidation
i. Combustion
A. State: At 298X
CH4 + 2O2  CO2 + 2H2O + Energy
i. C1 - C4 are gases
ii. Controlled oxidation
ii. C5-C17 are liquids and
Red hot Cu or
iii. Above C17 are solids RCH2OH
Fe tube
B. Boiling point: High I & P MO2O3
 In case of alkanes, boiling point increases with RCH3 RCHOH2O
increase in the molecular weight due to increase in (CH3COO)2Mn
the Vander Waal's forces. RCOOH

 In case of chain isomers, the isomer with more Note: Normal alkanes are resistant to the attack of
branches has low boiling point. oxidizing agents (e.g. KMnO4). But alkanes of the type R3–
Eg. Among isomers of pentane, the order of boiling CH are, however, attacked by KMnO 4 and are oxidized to
point is pentane > isopentane > neopentane. corresponding alcohols.
C. Melting point: Alkanes with even number of 'C' atoms CH3 – C–H + [O]  CH3 – C–OH
have more melting points than their preceding and C. Isomerization
succeeding odd 'C' alkanes because alkanes with even
CH3–CH2–CH2–CH3conc. HCl CH3 – OH
number of carbon atoms park closely which permits
D. Aromatization or Catalytic Reforming
greater intermolecular attractions.
D. Solubility: Alkanes are non-polar, so soluble in non
polar solvent [CCl4] and insoluble in polar solvent
[H2O] solubility decreases with increase in
molecular weight. CH3–(CH2)4–CH3Cr2O3/Al2O3 Benzene + 4H2↑
CH3
Chemical Properties
 Alkanes are extremely stable and inert. Thus called
paraffins. There are inactive towards acids, bases,
oxidizing and reducing agents.
A. Substitution reactions (FRSR) n-Heptane Cr2O3/Al2O3 Methyl benzene + 4H2↑
i. Halogenation E. Step-up reaction
CH4 Cl2 CH3Cl Cl2CH2Cl2 Cl2 CHCl3Cl2CCl4. CH3–CH3 CH2N2CH3–CH2–CH3
i.e. during halogenations, mixture of halogen → CH2N2 = Diazo methane
derivatives are formed. F. Reaction with steam

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 CH4 + H2O Ni/DCO + 3H2  Trans-alkene is obtained with Na/Liq. NH 3. (Birch
G. Pyrolysis or cracking reduction).
Decomposition of a compound on strong heating is RC  CR + 2[H] Na/Liq. NH3\o(H
called pyrolysis while conversion of high boiling B. By dehydrohalogenation of alkyl halides (-
hydrocarbon into low boiling hydrocarbon is called elimination)
cracking.  Reagents: alc. KOH or NaNH2
CH3CH2CH3 HeatCH4 + CH2 = CH2 CH3CH2Br alc.KOHCH2 = CH2 + KBr + H2O
Golden Key Points  Order of ease of dehydrohalogenation
 Characteristics reaction of alkane is free radical R-X: 3° > 2° > 1°
substitution reaction. (FRSR) w Reactivity order of R–X: R–I > R–Br > R– Cl
 Methane: w Saytzeff’s Rule: When two possible alkenes are
 Known as marsh gas or fire damp. obtained reaction then the alkene containing
 Obtained on a large scale from neutral gas by maximum number of alkyl group on double bonded
liquefaction. c-atoms will be the major product.
 CO + 3H2 Ni+CCH4 + H2O C. By dehalogenation of vicinal or geminal dihalides.
 LiG (liquefied Petactium Gas) is a mixture of n- w From vicinal dihalides
butane and iso-butane. Zn (dust) C2H5OHCH2 = CH2 + ZnX2
Interconversion of Alkanes w From geminal dihalides
 Ascent on alkane series CH3 CH X2 + Zn + X2 CH CH3 CH3 CH = CH - CH3 + ZnX2
i. Methane to Ethane
D. Dehydration of alcohols
CH4 Cl2CH3Cl Wurtz reactionCH3–CH3
Typing remaining
ii. Butane from ethane
CH3 – CH3 Al2O3CH3 – CH = CH2 + H2O
C2H6 Cl2C2H5Cl Wurtz reactionC2H5 – C2H5
 But with H2SO4 at 140°C, ether is obtained at 110°C,
Desired of alkane series sulphonic acids are formed.
 Ethane to methane H2SO4
CH3CH2HSO4
C2H6Cl2C2H5ClAq.KOHC2H5OH[O]CH3 110°C
CHO[O]CH3COOHCH3COONaNaOH/CaO CH4 CH3CH2OH
H2SO4
Alkenes CH3 CH2 O CH2 CH3
140°S
 Also known as olefins (oil forming compounds).
w Ease of dehydration of alcohol  3° > 2° > 1°
 Common name alkylene
w Most stable alkene is formed as major product (given
 General formula CnH2n
by saytzeff's rule).
 Carbon atom holding the double bond is Sp²
E. Kolbe's synthesis
hybridized, bond angle of 120° with triagonal planar
+ 2H2O Electrolysis\o\al(CH2
structure.
f. By dehydrogenation of alkenes
 They show chain ring chain or functional, position,
CH3–CH2–CH2–CH3Cr2O3.Al2O3CH3–CH = CH – CH3 + H2
geometrical and optical isomerization.
Physical Properties
Preparation of alkenes
A. Partial reduction of alkyne  First three alkenes are gases, next fourteen alkenes
 Cis-alkene is obtained with Lindlar's catalyst i.e., - are liquid and higher alkenes are solids.
Pd + BaSO4 or Pd + CaCO3 poisoned with sulphur or  Melting point and boiling point increases with the
quinoline. increase in molecular weight.
RC  CR + H2 Lindlar's \o(R Chemical properties
A. Addition reactions
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 i. Addition of H2 CH3 – CH = CH2 (i) B2H6CH3 CH2CH2OH
R–CH  CH + H2 Pt/Pd/NiR – CH3 – CH3 v. Addition of HOX
ii. Addition of halogens  Reaction is stereo - specific and HOX is added by anti
R – CH = CH2 Br2/CCl4R – addition.
 In the above reactions reddish brown orange  Electrophilic addition reaction following
colour of Br2 in CCl4 is discharged. markovnikov's rule.
iii. Addition of H–X CH3 – CH = CH2 + HOCl  CH3 –
a. Addition of HX to symmetrical alkene vi. Addition of sulphur monochloride, S2Cl2
CH2 = CH2 + HBr → CH2 – CH2 – Br CH2 + S2Cl2 CH2  CH2Cl CH2  CH2Cl
 Out of reactivity: HI > HBr > HBr > HF CH2 CH2 CH2
b. Addition of HX to unsymmetrical alkenes
S
 This gives two products
Mustard gas
CH3 – CH = CH3 + HBr H+CH3–\o\al(CH– CH3+ CH3CH2CH2 – Br
 This electrophilic addition reaction follows ( - dichloro diethyl sulphide)
Markonikov's rule.  Poisonous gas used in 1st world war.
 Markonikov's Rule: It states that negative part of the B. Oxidation reactions
addendum (attacking molecule) attack the carbon
i. Combustion
atom that contains lesser number of hydrogen atoms
C2 H4 + 3O2  2CO2 + 2H2O
or the electrophile attacks the carbon of double bond
in such a way that more stable carbocation is formed ii. By Baeyer's reagent
as intermediate.  Beyer's reagent is cold dilute aqueous solution of
Note: KMnO4. Alkenes are oxidized by Baeyer's reagent to
corresponding diols. It is syn addition of two OH
 Peroxide effect/Anti-markonikov's addition/ Kharasch groups.
effect
CH2 = CH2 1% Alk. KMnO4\o\al(CH2 –
 Addition of HBr to unsymmetrical alkene follows anti  Alkene de colourize KMnO4. Hence above is used to
Markonikov's rule in presence of peroxide. test unsaturation.
 Secondary free radical is more stable than primary free iii. Ozonolysis
radical.  This reaction is used to detect the position of
 Order of stability of free radical: 3° > 2° > 1° unsaturated ie.double or triple bond.
 So major product is obtained by attack of electrophile CH3–CH2 O3CH3 CO CH3 +HCHO
on secondary free radical.  The main use of Zn have is to remove H 2O2 that is
 Peroxide effect is not observed in case of addition of HF, formed during the reaction is also called the reductive
HCl and HI ozonolysis.
 If Zn is not used, then the intermediate H 2O2 that is
iv. Addition of H2O
formed during the reaction. Thus it is also called the
a. Alkenes add a molecule of water in presence of
reductive ozonolysis.
dil.H2SO4 to form alcohols.
 If Zn is not used, then the intermediate H 2O2 (being an
CH3 – CH2 + H2O H+CH3 – CH3
oxidizing agent) oxidise the aldehydes, (and not
b. Oxymercuration - demercuration ketones) into acids. Thus it is called the oxidative
 Product is alcohol obtained by adding water according ozonolysis.
to markovnikov's rule. CH3 – CH2O3CH3COCH3 + HCOOH
CH3 – CH2 (i) (CH3COO)2HgCH3 – CH3
Note: If its only said 'ozonolysis' that means its saying
c. Hydroboration - oxidation 'reductive ozonolysis.
 Product is alcohol obtained by adding according to
iv. Oxo reaction or hydroformylation
Anti-Markounikov rule.
 Addition of oxygen (Epoxidation)
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C = C+ O2 AgCH2 – CH2 Preparation of Alkynes
v. Oxidation by strong oxidizing agent A. Hydrolysis: With calcium carbide (CaC2) [WOHLER
 Agents may be hot alk. KMnO4, Acidic KMnO4, Acidic reaction]
K2Cr2O7 or NaIO4 + K/InO4 CaC2 + 2H2O → C2H2 (Ethyne) + Ca(OH)2
 In this oxidation reaction - With magnesium carbide
= CH2 part got oxidized to CO2 + H2O Mg2C3 + H2O → CH  C–CH3 + Mg(OH)2
= CHR part get oxidized to RCOOH B. From vicinal dichlorides
= CR2 part get oxidized to RCOR Br CH3 – CH2Bralc. KOHHC  CH+ KBr + H2O
(CH3)2 = CH2 KMnO4/H+(CH3)2C = O + CO2 + H2O C. Kolbe's Electrolysis
C. Allylic substitution Electrolysis\o\al(CH + 2CO2+ 2KOH+ H2
= CH2 + Br2 500°C D. Dehalogenation of tetrachloride
w It is free radical substitution and given with Cl 2 or Br2 CHBr2 – CHBr2 Zn dustCHCH + ZnBr2
at high temperature. E. From trihalides (Chloroform and Iodoform)
D. Isomerization 2CHCl3 6AgCH  CH + 6AgCl
w Reagent is Al2(SO4)3/AlCl3 and conc. H2SO4 F. Synthesis from C and H2 [Berthelot's reaction]
CH3CH2CH = CH2 Al2(SO4)3CH3CH= CH–CH3 + CH2 = \o\ 2C + H2 Electric arcC2H2
al(C–CH3 G. Formation of long chain alkyne
F. Polymerization CH2 CH2 CH  CH + Na → HC  CNa R–XHC C–R
nCH2 = CH2 1500 atm
(Low density polyethene) Physical properties
 State:
CH2 CH2
n i. C2–C4 = colourless gases
nCH2 = CH2 Zeigler Matta catalyst (High density polyethene) ii. C5–C12 = liquid
Golden Key Points iii. C13 and higher = solids
 The characteristics reaction of alkene is  The garlic order of acetylene is due to phosphine
Electrophilic Addition Reaction. impurity.
 Uses of Alkene Chemical properties
i. For manufacture of polyethene, plastic materials.  Alkynes are more reactive than alkenes towards
ii. For artificial ripening of fruits Nucleophilic Addition reaction
A. Addition reaction
iii. In oxy. Ethylene welding
i. Addition of halogens (Trans addition)
iv. As general anaesthetic (C2H4 with 100% O2)
CH3 – C  CH Br2CH3 – Br2H
Alkyenes  Reactivity order of X2: F2 > Cl2 > Br2 > I2
 General formula: CnH2n–2 ii. Additon f HX (cis-addition)
 Carbon containing  bond is sp hybridized and  Addition occurs+ according to Markounikov's rule.
contains 2x and 1  (sigma) bond; bond angle is 180° R–C  CH + HBr  R – CBr = CH2 HBrR – C Br2 – CH3
and shape is linears.  Reactivity order of HX: HI > HBr > HCl > HF
 Number of linear atoms in alkyne = number of sp iii. Addition f H2
carbons CH3 – C  C – CH3 +H2CH3–CH2–CH2–CH3
 Minimum number of carbon atoms in alkynes to show  Controlled addition of H2 with Pd + BaSO4 or
following isomerism Lindlor catalyst give alkene
i. Chain-5C ii. Position-4C iv. Addition of H2O (NAR)
iii. Functional-3C iv. Ring chain-3C  Nucleophilic Addition reaction: In there reactions
v. Geametricol-6C v. Optical-6C some heavy metal cations like Hg2+, Pb2+, Cu2+ are

Target MDS for CEE |333|

 used. There cation attract the e¯ of alkynes and R–C  CH AmmonicalR–C  C Cu
decreases the e¯ density and hense a nucleophile Note: There substitution reactions are given by 1-alkynes
can attack an alkynes. only. So they can be used to separate 1-alkynes from
 Alkynes add water in presence of dil. H 2SO and Hg2+ other substrates.
ions to form carbonyl compounds.
Eg. CH3 – C  C – CH3 Ammonical AgNO3No Reaction
 Acetylene is hydrated to acetaldehyde.;
CH3–CH = CH2 Ammonical AgNO3 No Reaction
 Higher alkynes are hydrated to ketones.
D. Isomerization
CH3–C  CH + H2SO4 HgSO4CH3 –
w When alkyne-1 is heated with alc. KOH, alkyne-2 is
TautomerizationCH3 – CH3
obtained.
v. Addition of AsCl3 (NAR)
CH3–CH2–C = CH alc. KOHCH3–C = C – CH3
CH = CH + AsCl3 Cu2Cl2Cl–CH= CH– AsCl3
w When 2-alkyne is heated with NaNH 2, 1-alkyne is
Notes: obtained.
w Lewisite gas was used in world war II. CH3–C = C – CH3NaNH2CH3–CH2–C = CH
w It is more poisonous than mustard gas. E. Polymerization
w Antidote of Lewisite gas is BAL (British Anti
Lewisite).
B. Oxidation reaction
i. Combustion (Complete oxidation) 3HC  CH Fe tube Benzene
C3H4 + 4O2 ¾® 3CO2 + 2H2O + heat CH3
ii. By Baeyer's Reagent
CH  CH 1% Alk. KMnO4\o\al(COOH (Oxolic acid)
CH3 – C  CH + [O] Alk. KMnO4CH3 – \o\al(C –
CH3
iii. Ozonolysis 3CH3 – C  CHFe tube H3C
CH3 – C  C – CH3 + O3 Zn+ H2O2 (mesitylene)
iv. By SeO2 (Selenium dioxide) Golden key points
w Acetylene is oxidized to glyoxol  Characteristic reaction of alkyne is Electrophilic
+ 2[O] ¾® Addition reaction.
v. By strong oxidizing agents  Liquid acetylene is explosive thus it is stored and
w Terminal alkyne gives formic acid as one of the transported in acetone solution.
product which is further oxidized to CO2.  Comparative study
CH3 – C  C–CH3 Hot.alk 2CH3– C –OH a. Bond length
CH3 – CH2 – C  CH H+CH3CH2COOH + HCOOH
1.54 A° → Alkane
C. Substitution reaction
1.34A° → Double bond of Alkene
w Given by 1-alkynes only due to their acidic
1.20A° → triple bond of Alkyne
character.
i. Reaction with NaNH2 b. Acidic character

CH  CH + NaNH2 ¾® CH  CNa + NH3 As % of S-charater in hybrid orbitals increases, acidic

nature increases.
w Alkene do not respond this reaction
ii. Reaction with ammonical AgNO3 CH  CH > CH2 = CH2> CH3 = CH3
w Tollens's reagent = Ammonical AgNO 3 (NH4OH + Overall acidic strength
AgNO3)
R–C  H AmmonicalR–C  C Ag
iii. Reaction with ammonical Cu2Cl2
w Ammonical Cu2Cl2 = [NH4OH + Cu2Cl2]
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 COOH OH
Note: All other compounds, not following Huckel's (4n+2) 
rule, are categorized under non-aromatic compound.

HCOOH > >CH3COOH > > H2O > R–

Benzene
OH > CH  CH > NH3 > CH2 = CH2> CH–CH3 v It was first isolated by Faraday from the cylinders of
c. Reactivity compressed illuminating gas obtained by the pyrolysis
of whale oil.
- Towards Electrophilic Addition Reactions.
v Hoffmann obtained benzene by fractional distillation
Alkene > Alkyne > Alkane
of coal tar.
- Towards Nucleophilic Addition Reaction
Structure of benzene
Alkyne > Alkene > Alkane
v The stability and the structure of benzene have been
d. Melting point and boiling point explained on the basis of two modern theories. These
Alkynes > Alkenes > Alkanes theories are:
1. Resonance or valence-bond theory
Aromatic Hydrocarbon
2. Molecular orbital theory
Aromaticity
 Proposed by Erich Huckel, also known as (4n+2) 
rule or Huckel's rule. I II

 The carbon compounds with the following 80% 20%

characteristics can exhibit aromaticity. Kekule's Structures Dewar's structures

i. Planarity v The carbon to carbon bond length in benzene has been

ii. Complete delocalization of the  electrons in the found to be 1.39 A°, which indicates C–C bond length
ring. in benzene is in between single and double bond
lengths.
v Greater the resonance energy greater will be the
iii. Presence of (4n+) electrons in the ring where n is
stability.
an integer (n=0,1,2 ………..). This is referred to as
Huckel's rule. v More the number of resonating structures, more will
Benzene
be the stability.
Orbital model of Benzene
v In benzene the total number of hybridized orbitals and
Eg. pure orbitals are 18 and 12 respectively.

It has 6 electrons v The total number of  and  bond in benzene are 12

and 3.
4n+2=6
 n=1 Preparation of Benzene
A. Fractional distillation of coal tar.
Anti-aromarity upto 170°C (Benzene, toulene,
Light oil xylene)
v According to Huckel,”monocyclic, planer and
completely conjugated polyenes containing (4n+2) 170°C - 230°C
Middle oil (Phenol, cresol)
electrons are destabilized by resonance show anti- Fractional
Coal tar
aromatic character.” distillation 230°C - 270°C Heavy oil (Naphthalyne)

270°C - 360°C
Green oil (Anthracene)

B. From acetylene (By cyclic polymerization)

Cyclopropane 2 electrons, no conjugation
w Benzene was first synthesized by Berthelot by
passing acetylene through red hot tube.

Target MDS for CEE |335|

 Benzene v It is an extremely poisonous substance, Inhalation of
vapours or absorption through skin has a toxic effect.
Chemical properties
 CH Red hot v Characteristic reaction of Benzene is Electrophilic
substitution reaction.
CH
A. Addition reaction
C. From Benzoic acid (sodalime decarboxylation) Complete Hydrogen
COOH

CaO + 3H2 Ni
+ NaOH + Na2CO3 + H2O
 Partial hydrogen
Sod. benzoate Benzene

D. From Phenol (By deoxygenation)

OH + Na/Liq.NH3
ii. Addition of O3
+ Zn duct

Benzene + 3O2  Benzene triozonide
(i) O3 CHO
E. From Aniline 3 (Reductive
NH2 (ii) H2O/2n ozoanlysis)
N2Cl CHO
(Glyoxal)
+ HNO2 + HCl + 2H2O SnCl2 + NaOH
+ N2 + HCl
 2 [H]
Anline
(Benzene diazonium (Benzene) CHO
chloride) (i) O3
3 (Oxidative
F. From Chlorobenzene (ii) H2O/2n ozoanlysis)
CHO
Cl (Oxylic acid)
iii. Addition of X2
Ni=Al Alloy Cl
+ 2[H] + HCl
 Cl Cl
Chlorobenzene
(Benzene)
Cl
Cl
G. From Benzene sulphiric acid
Cl
SO3H
C6H6 Cl6
3Cl2
+ H2O + H2SO4 v Benzene hexachloride or lindane or 666
v Used as insecticide
(Benzene (Benzene)
(Super
Sulphoric Heated v This reaction proceeds by free radical addition
acid) stem) mechanism.

Physical properties Note: Benzene does not give addition reaction Br 2/CCl4 or
alkaline KMnO4.
v Benzene is colourless, mobile, and volatile liquid. It is
characteristic odour. B. Electrophilic substitution reaction
v It is highly inflammable and burns with sooty flame.
v It is lighter than H2O and insoluble in water. i. Halogenation
v It is used as solvent and also soluble in organic
solvents.

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 Cl CH3
Al Cl3 CH
Al Cl3 + CH3  CH2CH2 Cl CH3
+ Cl2 + HCl
Fa Cl3 Cumene
(Isopropyl Benzene)
CH3 CH3 CH3
 Since intermediate is carbocation in Friedel craft's
Cl
Al Cl3 reaction, there occurs H¯ or, hydride shift.
+ Cl2 +
v. Gattermann's Koch reaction
(minor) CHO
Cl
(major) Al Cl3
+ CO  HCl
iii. Nitration
NO2
vi. Gattermann's aldehyde synthesis
CHO
con. HNO3 + conc. H2SO4
(Nitrating mixture) Al Cl3
+ HCN  HCl
Nitrobenzene
conc. HNO3 acts as to a base. The electrophiles used in the aromatic substation are:
iii. Sulphonation Name of Electrophile Source
SO3H substitution Involved Cl²
reaction (Chloronium)
i. Chlorination Cl¯ (Chloronium) Cl2 + AlCl3 or FeCl3
+ fuming H2SO4 + H2O
ii. Nitration NO2+ (Nitronium) Conc. HNO3 +
conc. H2SO4
Benzene sulphonic iii. Sulphonation SO3 (Sulphur Fuming sulphuric
acid trioxide) acid conc. H2SO4
iv. Friedel crafts R+ (Alkyl Fuming sulphuric
Friedel crafts reaction alkylation carbonium ion) acid conc. H2SO4
v Alkylation or acylation in presence of Lewis acid v. Friedel craft's R–(Acyl ROCl + AlCl3
[FeCl3, AlCl3, etc] acylation carbonium)
v CS2 or nitrobenzene is used as solvent in Friedel crafts C. Oxidation reaction
reaction. i. Combustion
v Friedel crafts Alkylation. 2C6H6 + 15O2 6CO2 + 3H2O
CH3 ii. Catalytic oxidation
Al Cl3
+ CH3  Cl OH
+ HCl
300°C
Methyl Benzene (Phenol)
Benzene
Cl2O5
v Friedel craft Acylation + O3
O CH - CO
(Benzene) 450°C CH - COOH H2O O
C  CH3 CH - COOH CH - CO
Al Cl3 + HCl
+ CH3 COCl (Maleic acid) (Maleic anhydride)

Some special reactions

Note: i.
Red hot
2 + H2
Fe tube

(Biphenyl)
Target MDS for CEE |337|
ii. Side chain oxidation 3. Antiknocking compounds: To reduce the knocking
At least one benzyllic –H containing alkyl benzene property or to improve the octane number of a fuel
gives benzoic acid in presence of strong oxidizing certain chemicals are added to it known as antiknock
agents like K2Cr2O7/H+, KMnO4/H+, KMnO4/OH¯; compounds.
regardress the length of the alkyl benzene Eg. Tetraethyl Led (TEL) i.e. (C2H5)4Pb.
CH3 CH3CH3 CH2 CH2 ........... COOH However, because of lead poisoning caused by TEL,
nowdays, in developed countries, a new compound
[H+] + CO2 + H2O
+ , , , cyclopenta dienyl manganese carbonyl (called as AK -
CH3 33 - X) is used as antiknocking compound.
CH3 4. Cetane number: Quality of diesel fuel is measured in
CH3
terms of cetane number.
Flash Point
The lowest temperature at which an oil gives sufficient
CH3
vapours to forms an explosive mixture with air is
C CH3 [1-Butyl Benzene] referred to as flash point of the oil. It is usually
CH3 determined by means of "Abel's apparatus".
But,
Doesnot give benzoic acid because of absence of benzylic
H.
Sources of Hydrocarbons
 Petroleum and natural gas are a major source of
aliphatic hydrocarbon.
 Coal tar is a major source of aromatic hydrocarbon. PAST QUESTIONS
Characteristics of hydrocarbons
HYDROCARBONS
1. Knocking: The metallic sound during working of on
internal combustion engine is termed as knocking, The 1. Liquid hydrocarbons can be converted into
fuel which has minimum knocking property is always gaseous hydrocarbons by: [BPKIHS 2019]
preferred. The tendency to knock falls off in the a. Cracking b. Oxidation
following order: Straight chain alkanes > branched c. Disproportionation d. Knocking
chain alkanes > Olefins > Cyclo alkanes > aromatic 2. Gobar gas contains [BPKIHS 2019]
hydrocarbons.
a. CH4 + CO2 b. CO + H2
2. Octane number: Quality of petrol or gasoline is c. CH2 + O2 d. CO + H2 + N2
measured in terms of octane number. It measures the
3. Which of the following contains isopropyl group:
knocking character of fuel. The octane number of a
given sample may be defined as the percentage of by [BPKIHS 2018]
volume of iso-octane present in a mixture of iso- a. 2 methyl butane
octane and n-heptane which has the some knocking b. 2,2 dimethyl propane
performance as the fuel itself. c. 2,2,2 trimethyl pentane
CH3CH2CH2CH2CH2CH3 d. None
CH3 – \o(C – 4. In benzene  electron is attached to [BPKIHS
For eg. a given, sample has the knocking performance 2018]
equivalent to a mixture containing 60% iso-octane and a. 2 carbons b. 3 carbons
40% heptanes. The octane number of the gasoline is, c. 4 carbons d. 6 carbons
therefore 60. 5. The hybridization of methane is [BPKIHS 2017]
- Higher the octane number, better the fuel. a. SP3 b. SP2
- isomerization Alkylation, Aromatization increases c. SP d. dsp2
the octane number.
|338| General Medicine - Loading Dose
6. The number of & c–c bond in ethyne 17. Which of the following has highest octane no. of
100? [BPKIHS 2008]
[BPKIHS 2017]
a. 2, 2 Dimethylpentane
a. 1& 3 b. 1& 2 
b. 2, 2, 4 Trimethylhexane
c. 2& 2  d. 3  only
c. 2,2,4 Trimethylpentane
7. Which of the following has 0 dipole moment d. n-octane
[BPKIHS 2017, IOM 2018] 18. LPG gas used for cooking purposes contain.
a. CHCl3 b. CCl4 [BPKIHS 2006]
c. CHCl2 d. CH3Cl
a. Methane b. Propane
8. The no. of alkyl groups in isobutene is c. Mixture of butane and isobutane
d. Mixture of propane and ethane.
[BPKIHS 2017, 2002]
a. 1 b. 2 19. Which of the following is obtained when acetylene
c. 3 d. 5 reacts with conc. H2SO4? [BPKIHS 2006]
a. Mesitylene b. Ethylene
9. TEL is used [BPKIHS 2017, 2004]
c. Acrolein d. Ethylidene hydrogen
a. As petrol additive sulphate
b. To decrease volatility of the petroleum product
c. For hydrogenation of oil 20. Ozonolysis of propene gives: [BPKIHS 2003]
d. None a. Formic acid and formaldehyde
b. Acetic acid and acetaldehyde
10. TEL is used as [BPKIHS 2015]
c. Formic acid and acetic acid
a. Petroleum additive b. Bleaching agent d. Formaldehyde and acetaldehyde
c. Oxidizing agent d. All
21. Which of the following is most stable?
11. Which of the following Rxn doesn't involve metal
or metallic salt? [BPKIHS 2015] [BPKIHS 2002]
a. Wurtz Rxn b. Kolbe's electrolysis a. (CH3)2 C=CH2 b. (CH3)CH=CH (CH3)
c. Frankland Rxn d. Transesterification c. (CH3)2 C=C (CH3)2 d. All are equally stable

12. Bayer's Reagent is [BPKIHS 2015] 22. Carbide of metal on hydrolysis form hydrocarbon,
also give test with Tollen’s reagent is: [IOM 2019]
a. Alkaline KMNO4 b. Acidified KMnO4
c. Alkaline K2Cr2O7 d. Acidified K2Cr2O7 a. Methane b. Ethane
c. Ethene d. Ethyne
13. Tollen's reagent give white ppt. With [BPKIHS
2014] 23. Which of the following increases anti-knocking
properties? [IOM 2018]
a. 1- Butyne b. 2 -Butyne
c. 1- Butene d. 2-Butene a. Cyclic chain olefins
b. Branched chain olefins
14. In the given structure, number of σ and π bonds c. Aromatic chain olefins
are: [BPKIHS 2011] d. Straight chain olefins
C¿ 24. 2,2 dibromo propane is formed by [IOM 2017]
a. 9σ and 9 π b. 9σ and 11 π
a. CH3 -C  CH + HBr
c. 11σ and 9 π d. 11σ and 11 π b. CH3 -C  CH + 2HBr
15. Calorific value per – CH2 is minimum in: c. CH3 -C C -CH3 + HBr
d. CH3 - C C- CH3 + 2HBr.
[BPKIHS 2010]
a. Cyclopropane b. Cyclobutane 25. Heat involved in reaction C2 H6 + O2→ 2CO2 + 3H2O
c. Cyclopentane d. Cyclohexane is [IOM 2017]
a. Heat of formation
16. CH3CHCl2 + NaNH2 = ? [BPKIHS 2010]
b. Heat of combustion
a. CH3 – CH = CH2 b. CH3–CH= CH2 c. Heat of neutralization
c. CH3–CH d. CH3 – CH  d. Heat of vaporization
Target MDS for CEE |339|
26. Most volatile alkane among the following is d. None
[IOM 2016] 36. CH3CH2CH2OH⃗
conc. H 2 SO 4 X⃗
Br2 Y⃗
alc.KOH Z
a. n-Hexane b. Isopentane identify Z in the chemical reaction. [IOM 2009]
c. Neopentane d. n-Butane a. CH3CH(NH2) CH(NH2)
27. Sodium salt of the succinic acid on electrolysis b. CH3CHOHCH3
gives [IOM 2016] c. CH3CH(OH)CH(OH)
a. Alkanes b. Alkenes d. CH3C CH
c. Alkyl halides d. Carboxylic acids 37. Which of the following reacts with alcoholic KOH
28.Which of the following reducing agent reduces to give alkene? [IOM 2009]
carboxylic acid directly to alkane? [IOM 2016] a. Alkane b. Alkyl halide
a. LiAlH4 b. NaBH4 c. Alcohol d. Acid
c. Na + C2H5OH d. HI + red phosphorus 38. According to Markownikov's rule, addition of HBr
29. Anti-knocking agent is to propylene will give the product [IOM 2008]
a. CH3CH2 – CH2Br b. CH3CHBr – CH3
[IOM 2015, MOE 2061(Kartik)]
c. CH3CHBr CH2Br + H2
a. Ethyl alcohol b. Tetra ethyl lead d. There is no reaction
c. Lead acetate d. Sodium acetate
39. Methane is formed from the hydrolysis of:
30.A gas decolorised alkaline KMnO4 solution but
does not give precipitate with ammonical AgNO 3 [IOM 2008, 1996, Model Question by MOE, MOE
solution. The gas is [IOM 2014] 2070, MOE 2059]
a. Acetylene b. Methane a. Calcium carbide b. methanol
c. Ethylene d. Ethane c. aluminum carbide d. ethanol

31. Which has the highest knocking property? 40. On reaction with Baeyer's Reagent, Ethylene and
Acetylene form: [IOM 2006]
[IOM 2014]
a. Formic acid and the acetic acid
a. Aromatic hydrocarbon b. Oxalic acid and ethylene glycol
b. Branched chain olefins c. Ethylene glycol and oxalic acid
c. Heterocyclic compounds d. Acetic acid and formic acid
d. Straight chain olefins
41. Cracking" of hydrocarbon is the process in which,
32. n-propyl bromide on reduction with alc. KOH
gives [IOM 2014] [IOM 2003]
a. Propane b. Propene a. Lower boiling hydrocarbons are changed into
higher boiling hydrocarbons.
c. Ethene d. Propyne
b. Higher boiling hydrocarbons are changed into
33. Propyne and propene can be distinguish by lower boiling hydrocarbons by the application of
heat
[IOM 2013, 2011, 2003,1997, MOE 2065(Baisakh)]
c. Production of petroleum from crude oil
a. CuSO4 b. Br2/CCl4 d. Separation of smaller hydrocarbons from their
c. KMnO4 d. AgNO3/Ammonia mixture.
34.Which of the following undergoes elimination & 42. The catalyst used in hydrogenation of oil is:
substitution reaction but not addition reaction?
[IOM 1993]
[IOM 2012, KU 2015] a. Molybdenum b. Iron
a. Alkane b. Alkene c. Platinum d. Nickel
c. Alkyne d. Benzene
43. Double bond in alkene represents: [KU 2019]
35. In green house effect, Methane causes [IOM 2009] a. Non-polar b. Polar
a. Absorption of heat c. Saturated d. Unsaturated
b. Reflection of heat
c. Destroy green house
|340| General Medicine - Loading Dose
44. Intermediate form CH3Cl in presence of AlCl3 in 53. An organic compound on heating with CuO
Benzene [KU 2018] produces CO2 but no water. The compound may be
a. C6H5+ b. CH3+ [MOE 2069 (Magh)]
c. Cl¯ d. Cl+
a. Methane b. Chloroethane
45. Which of the following reacts with Na and liquid c. Carbon tetrachloride
NH3 [2018] d. Chloroform
a. CH3CH C  C – CHH2CH3 54. Ethene on reaction with Baeyer's reagent produce
b. CH3CH2C  CH
c. CH3CH  CH – CH3 [MOE 2069 (Bhadra.]
d. CH3CH2C = C – CH2CH3 a. Formic acid b. Ethylene glycol
c. Epoxy ethane d. Formaldehyde
46. When ethene reacts with water in presence of
sulphuric acid, CH3CH2OH is formed, which type of 55.Ethyne on reaction with alkaline potassium
reaction in this [KU 2017] permanganate yields [MOE 2068 (Kartik)]
a. Substitution b. Acid base reaction a. Oxalic acid b. Acetaldehyde
c. Hydrolysis d. Addition c. Ethanoic acid d. Ethylene glycol

47. Which of the following form cyclic alkane 56. Cane sugar becomes black on treatment with conc.
Sulphuric acid due to: [MOE 2068 (Ashad.]
[KU 2017]
a. Oxidation b. Hydrolysis
a. 1,2 dibromoethane b. 1,1 dibromopropane c. Dehydration d. Hydration
c. 1,4 dibromobutane d. 1,2 dibromobutane
57. Ethyne on reaction with acidified potassium
48. When ethene reacts with bromine then 1, 2–
dichromate yields [MOE 2068 (Ashad)]
dibromoethane is obtained, the intermediate is
a. Oxalic acid b. Acetaldehyde
[KU 2016] c. Ethanoic acid d. Ethylene glycol
a. Negative charge b. Free radical 58. When alkyl halide is reacted in the presence of
c. Electrophile d. Nucleophile sodium, alkane is formed. The reaction is
49.When benzene reaction with chlorine, presence of
[MOE 2067 (Kartik)]
sunlight the product is [KU 2016]
a. Grignard’s reaction
a. C6H5Cl6 b. C6H6Cl6 b. Reimer Tiemann’s reaction
c. C6H6Cl d. CCl4 c. Kolbe’s electrolysis
50. Which of the following reagents and conditions d. Wurtz reaction
would best serve to convert but - 1 - yne to 1, 1 – 59. Alkaline KMnO4 solution is treated with alkene to
dibromobutane? [KU 2015] give a blue colouration, the test is
a. 1 equivalent of Br2
[MOE 2067 (Kartik)]
b. 2 equivalents of Br2 followed by 1 equivalent of
KOH a. Bayer’s test b. Grignard’s test
c. 2 equivalents of HBr, no peroxides c. Lucas test d. Victor Mayer’s test
d. 2 equivalents of HBr, with peroxides 60.Which of the following compounds can not be
51.Which of the following compounds undergoes synthesized by the Wurtz reaction?
electrophillic addition reaction? [KU 2012]
[MOE 2067 (Ashad.]
a. Benzaldehyde b. Benzoic acid
a. Ethane b. Butane
c. Ethoxyethane d. Propene
c. Hexane d. methane
52.The compound having only primary hydrogen
61.The compound which will give only acetaldehyde
atoms is [KU 2011]
on ozonolysis is [MOE 2008 (2065 Magsir)]
a. Isobutene b. 2, 3- Dimethyl butene
a. l - butene b. 2 – butene
c. Cyclohexane d. Propyne
c. ethene d. propene

Target MDS for CEE |341|

62.The ozonolysis of the ethylene followed by the 3. The number of sigma () and pi () bonds in pent-
reduction by Zn dust and water gives 2-en-4-yne is : [NEET 2019]
[MOE 2008 (BE)] a. 10bonds and 3bonds
b. 8bonds and 5bonds
a. Formic acid b. Formaldehyde
c. Acetaldehyde d. Acetic acid c. 11bonds and 2bonds
d. 13bonds and no bonds
63.A mixture of methane, Ethylene and acetylene is
4. The most suitable reagent for the following
passed through ammoniacal Cu2Cl2 solution in a
conversion, is: [NEET 2019]
tube. Then the mixture of gases coming out of the
tube is [MOE 2056 (Ashwin)]
a. Methane and acetylene
b. Methane and ethylene
c. Ethylene and acetylene
d. Acetylene a. Na/liquid NH3 b. H2, Pd/C, quinoline
c. Zn/HCl d. Hg2+/H+, H2O
64.Which one of the olefins (alkenes) gives 2
molecules of formaldehyde on ozonolysis? 5. Among the following, the reaction that proceeds
through an electrophilic substitution, is:
[MOE 2053 (Bhadra 30)]
a. CH2 = CH2 b. CH3–CH = CH–CH3 [NEET 2019]
c. CH2 = CH – CH3 d. CH3–CH2=CH–CH2 + Cu2Cl2
N2Cl¯
65.Which of the following contains +ve acidic
hydrogen [MOE 2052 (Falgun 26)] a.

a. Ethene b. Benzene
c. Ethyene d. Ethane + Cl2
AlCl2
Cl + HCl

66.Propylene when treated with 1% potassium b.

permanganate the pink colour is discharged due to Cl
Cl
formation of [MOE 2071(Mangsir27)]
UV light
a. Propanol b. Propylene glycol + Cl2 Cl Cl
c. Propanal d. Propanone
Cl Cl
c.
Probable Questions
1. An alkene on ozonolysis gives methanal as one of heat
CH2OH+HCl
the product. Its structure is: [NEET 2020]
CH2Cl +H2O

d.
a. b. 6. An alkene "A" on reaction with O 3 and Zn–H2O
gives propanone and ethanal in equimolar ratio.
Addition of HCl to alkene "A" gives "B" as the major
product. The structure of product "B" is:
c. d.
[NEET 2019]
2. Elimination reaction of 2-Bromo-pentane to form
pent-2-ene is: [NEET 2020]
(1) b-Elimination reaction
(2) Follow Zaitsev rule
(3) Dehydrohalogenation reaction
a.
(4) Dehydration reaction
a. (1), (2), (4) b. (1), (2), (3)
c. (1), (3), (4) d. (2), (3), (4)
|342| General Medicine - Loading Dose
 a. CH3CH2CH2Cl Mg/ether
b. CH3COCl CH3MgX
b. c. CH3CH = CH2 B2H6
d. CH3– CH3 P/HI
14.Which of the following shows only one
brominated compound
c.
a. Butene-2 b. 2, 2-dimethylpropane
c. Butyne-1 d. Butanol-3
d. 15. Kerosene is used as fuel because it is
7. Hydrocarbon a. reacts with bromine by a. Less volatile b. More volatile
substitution to form an alkyl bromide which by c. Cheap d. Abundantly available
Wurtz reaction is converted to gaseous 16.Which of the following statements is not true
hydrocarbon containing less than four carbon for ethane
atoms. a. is [NEET 2018] a. It can be chlorinated with chlorine
a. CH CH b. CH2=CH2 b. It can be catalytically hydrogenated
c. CH3–CH3 d. CH4 c. When oxidised produces CO2 and H2O
8. Which of the following molecules represents d. It is a homologue of iso-butane
the order of hybridisation sp², sp², sp, sp from 17. Petroleum refining is
left to right atoms? [NEET 2018] a. Distillation of petroleum to get different
a. HC  C – C  CH fractions
b. CH2 = CH – C  CH b. Obtaining aromatic compounds from aliphatic
c. CH2 = CH – CH = CH2 compounds present in petroleum
d. CH3 – CH = CH – CH3 c. Cracking of petroleum to get gaseous
hydrocarbons
9. The decreasing order of boiling points is d. Purification of petroleum
a. n-Pentane > iso-Pentane > neo-Pentane
18.Which of the following is not formed by the
b. iso-Pentane > n-Pentane > neo-Pentane
reaction of Cl2 on CH4 in sunlight
c. neo-Pentane > iso-Pentane > n-Pentane
d. n-Pentane > neo-Pentane > iso-Pentane a. CHCl3 b. CH3Cl
c. CH3CH3 d. CH3CH2CH3
10.To prepare a pure sample of n-hexane using
sodium metal as one reactant, the other 19.Which of the following compounds is insoluble
reactant will be even in hot concentrated H2SO4

a. n-propyl bromide a. Ethylene b. Benzene

b. Ethyl bromide and n-butyl bromide c. Hexane d. Aniline
c. Ethyl chloride and n-butyl chloride 20.A reaction between methyl magnesium
d. Methyl bromide and n -pentyl chloride bromide and ethyl alcohol gives
11.Which of the following compounds is used in a. Methane b. Ethane
antiknock compositions to prevent the c. Propane d. Butane
deposition of oxides of lead on spark plug, 21.Methane and ethane both can be obtained in
combustion chamber and exhaust pipe single step from
a. Glycerol b. Glycol a. CH3I b. C2H5I
c. 1, 2-dibromoethane c. CH3OH d. C2H5OH
d. Benzene
22. Paraffin wax is
12. What is freon-12 a. Ester
a. Pesticide b. Refrigerant b. Alcohol
c. Solvent d. Lubricant c. Unsaturated hydrocarbon
13.Which of the following reactions will not give d. Saturated hydrocarbon
propane
Target MDS for CEE |343|
23. In the preparation of alkanes; a concentrated 33. A mixture of ethyl iodide and n-propyl iodide is
aqueous solution of sodium or potassium salts subjected to Wurtz reaction. The hydrocarbon
of saturatedcarboxylic acid are subjected to that will not be formed is
a. Hydrolysis b. Oxidation a. n-butane b. n-propane
c. Hydrogenation d. Electrolysis c. n-pentane d. n-hexane
24. Propane is obtained from propene, by which of 34. Daily use candles (paraffin wax) contain
the following methods a. Higher saturated hydrocarbon
a. Wurtz reaction b. Dehydrogenation b. Lower saturated hydrocarbon
c. Frankland reaction c. Higher unsaturated hydrocarbon
d. Catalytic hydrogenation d. Lower unsaturated hydrocarbon
25. Which of the following does not give alkane 35. Normal butane convert into isobutane by
a. Reaction of CH3I with Na in ether a. LiAlH4 b. AlCl3
b. Reaction of sodium acetate with sodalime c. NaBH4 d. Zn/HCl
c. Electrolysis of concentrated sodium acetate 36. Alcoholic solution of KOH is used for
solution
d. Reaction of ethyl chloride with alc. KOH a. Dehydration
b. Dehydrogenation
26.Which of the following compound has c. Dehydrohalogenation
maximum boiling point d. Dehalogenation
a. n-hexane b. n-pentane 37.Maximum carbon-carbon bond distance is
c. 2, 2-dimethyl propane
found in
d. 2-methyl butane
a. Ethyne b. Ethene
27.Aqueous solution of the following compound on c. Ethane d. Benzene
electrolysis gives ethane
38. Methane can be prepared by
a. Acetic acid b. Acetamide
a. Wurtz's reaction
c. Potassium acetate d. Ethyl acetate
b. Decarboxylation
28. Sodium ethoxide is a specific reagent for c. Hydrogenation reaction
a. Dehydration b. Dehydrogenation d. All of these
c. Dehydrohalogenation 39. Which one of the following compounds does
d. Dehalogenation
not form an ozonide
29. Which of the following will have least hindered a. Ethene b. Propyne
rotation about carbon-carbon bond c. Propene d. Propane
a. Ethane b. Ethylene 40. 2-Methylbutane on reacting with bromine in
c. Acetylene d. Hexachloroethane
the presence of sunlight gives mainly
30.Which of the following represents the most a. 1-bromo-2-methylbutane
oxidized form of hydrocarbon b. 2-bromo-2-methylbutane
a. CO2 c. RCOOH c. 2-bromo-3-methylbutane
b. RCHO d. RCOOOH d. 1-bromo-3-methylbutane
31.Which one gives only one monosubstitution 41. Of the five isomeric hexanes, the isomer which
product on chlorination can give two monochlorinated compounds is
a. n-pentane b. Neopentane a. n-hexane
c. Isopentane d. n-butane b. 2, 3-dimethylbutane
c. 2, 2-dimethylbutane
32.Photochemical chlorination of alkane is
d. 2-methylpentane
initiated by a process of
a. Pyrolysis b. Substitution 42.The product obtained on reaction of C2H5Cl with
c. Homolysis d. Peroxidation hydrogen over palladium carbon is
a. C3H8 b. C4H10

|344| General Medicine - Loading Dose

 c. C2H6 d. C2H4 52. Isopropyl alcohol is obtained by reacting which
43.Silver acetylide when heated with HCl gives of the following alkenes with conc. H2SO4 and
H2O
a. C2H2 b. H2
c. C2H4 d. None of these a. Ethylene
b. Propylene
44.CH4 is formed when c. 2-methyl propene
a. Sodium acetate is heated with sodalime d. Isoprene
b. Iodomethane is reduced
53.Which of the following is not used to distinguish
c. Aluminium carbide reacts with water
ethene from ethane
d. All of these
a. Iodine in CCl4 b. Bromine in CCl4
45. Addition of bromine to 1, 3-butadiene gives c. Alkaline KMnO4 d. Ammonical Cu2Cl2
a. 1, 2 addition product only
54. A hydrocarbon X adds on one mole of hydrogen
b. 1, 4 addition product only
c. Both 1, 2 and 1, 4 addition products to give another hydrocarbon and decolourised
d. No reaction bromine water. X reacts with KMnO 4 in
presence of acid to give two moles of the same
46. Ethene when treated with Br 2 in the presence
carboxylic acid. The structure of X is
of CCl4 which compound is formed
a. CH2=CH-CH2CH2CH3
a. 1, 2-dibromoethane b. CH3CH2CH2-CH=CHCH3
b. 1-bromo-2-chloroethane c. CH3CH2CH=CHCH2CH3
c. Both a. and b. d. CH3CH=CHCH2CH2CH3
d. 1, 1, 1-tribromoethane
55.A gas formed by the action of alcoholic KOH on
47. Ethylene may be obtained by dehydration of
ethyl iodide, decolorises alkaline KMnO4
which of the following with concentrated H 2SO4
solution. The gas is
at 160-170oC
a. CH4 b. C2H6
a. C2H5OH b. CH3OH c. C2H4 d. C2H2
c. CH3CH2CH2OH d. (CH3)2CHCH2OH
56.Ethyl bromide gives ethylene when reacted
48.When 3, 3-dimethyl-2-butanol is heated with
with
H2SO4 the major product obtained is
a. Ethyl alcohol b. Dilute H2SO4
a. cis and trans isomers of 2, 3-dimethyl-2-butene c. Aqueous KOH d. Alcoholic KOH
b. 3, 3-dimethyl-1-butene
c. 2, 3-dimethyl-2-butene 57. The compound formed by passing ethylene gas
d. 2, 3-dimethyl-1-butene into cold alkaline solution of KMnO4 is

49. Which of the following compounds represents a. Ethyl alcohol b. Acetaldehyde

c. Acetic acid d. Ethylene glycol
acrylonitrile
a. Vinyl cyanide b. Cyanoethene 58.Which decolorize aqueous bromine and gives
c. Prop-2-ene nitrile white fumes of HCl on reaction with PCl5
d. All of them a. CH3COCH2CHCH2
50. Ozonolysis of which one of the following will b. CH3CH2CH2CH2CH3
c. CH3CH=CHCH2CH2OH
give two molecules of acetaldehyde
d. CH3OCH2CH2CH2CH2OH
a. 1-butene b. 2-butene
c. 1-pentene d. 2-pentene 59. In the presence of peroxide, hydrogen chloride
and hydrogen iodide do not give anti-
51. In which of the following, addition of HBr does
Markovnikoff’s addition to alkenes because
not take place against Markownikoff's rule or
a. Both are highly ionic
Anti-Markownikoff addition of HBr is not
b. One is oxidising and the other is reducing
observed for
c. One of the steps is endothermic in both the
a. Propene b. But-1-ene cases
c. But-2-ene d. Pent-2-ene d. All the steps are exothermic in both the cases

Target MDS for CEE |345|

60. Ethylene is converted to X on passing through a a. Ethene b. Ethyne
mixture of an acidified aqueous solution of c. Ethane d. Methane
palladium chloride and cupric chloride. Which 70.The major product formed when propene
of the following reagents readily take part in reacts with Hbr in presence of peroxides is
addition reaction with X
a. n-propyl bromide
a. Br2 b. HBr b. Isopropyl bromide
c. HCl d. HCN c. n-propyl alcohol
61. Alkene R-CH=CH 2 reacts readily with B2H6 and d. 1, 3-dibromopropane
the product on oxidation with alkaline 71. Ethyl hydrogen sulphate is obtained by the
hydrogen peroxides produces reaction of H2SO4 on
a. R – CH2 – CHO b. R – CH2 – CH2 – OH a. Ethylene b. Ethane
c. R – CH3 d. R – c. Ethyl chloride d. Ethanol
62. Ozonolysis of 2-methyl butene-2 yields 72.When butene-1 is mixed with excess of
a. Only aldehyde bromine, the expected reaction product is
b. Only ketone a. 1, 2-dibromobutane
c. Both aldehyde and ketone b. 1, 1-dibromobutane
d. None of these c. 2, 2-dibromobutane
63. Ethyl alcohol on heating with conc. H 2SO4 gives d. Perbromobutane
a. CH3COOC2H5 b. C2H6 73.A compound ‘X’ on ozonolysis forms two
c. C2H4 d. C2H2 molecules of HCHO. Compound ‘X’ is
64. Monohalides on reacting with alcoholic KOH a. C2H4 b. C2H2
give c. C2H6 d. C6H6
a. Alkanes b. Alkenes 74. “The negative part of addenda adds on to the
c. Alkynes carbon atom linked with least number of
d. Aromatic hydrocarbons hydrogen atoms”. This statement is called
65. Ethylene is a member of..... series a. Thiele's principle
a. Alkyne b. Olefin b. Bayer's strain theory
c. Paraffin d. Amine c. Markownikoff's rule
d. Peroxide effect
66. n-propyl bromide on treatment with ethanolic
potassium hydroxide produces 75.3-Phenylpropene on reaction with HBr gives
(as a major product)
a. Propane b. Propene
c. Propyne d. Propanol a. C6H5CH2CH(Br)CH3
b. C6H5CH(Br)CH2CH3
67.The dehydrohalogenation of neopentyl c. C6H5CH2CH2CH2Br
bromide with alcoholic KOH mainly gives d. C6H5CH(Br)CH=CH2
a. 2-methyl-1-butene
76. A metallic carbide on treatment with water
b. 2-methyl-2-butene
gives a colourless gas which burns readily in air
c. 2, 2-dimethyl-1-butene
and which gives a precipitate with ammoniacal
d. 2-butene
silver nitrate solution. Gas evolved is
68.The reaction
a. Methane b. Ethane
CH2 = CH2 + H2 NiCH3 – CH3 is called c. Acetylene d. Ethylene
a. Wurtz's reaction 77.Identify the product D in the following series of
b. Kolbe's reaction reaction
c. Sabatier and Senderen's reaction CH3COOH LiAlH4A H+B Br2C a/cD
d. Carbylamine reaction a. Methane b. Alcohol
69. A gas decolourises Bayer's reagent but does c. Acetylene d. Benzaldehyde
not react with Tollen's reagent, this gas is 78. Acetylenic hydrogens are acidic because
|346| General Medicine - Loading Dose
 a. Sigma electron density of C–H bond in acetylene 86. When acetylene reacts with HCl in the presence
is nearer to carbon, which has 50% s-character of HgCl2, the product is
b. Acetylene has only one hydrogen on each carbon a. Methyl chloride b. Dichloroethane
c. Acetylene contains least number of hydrogens c. Vinyl chloride d. Ethylidine chlorid
among the possible hydrocarbons having two
carbons 87.When propyne reacts with aqueous H 2SO4 in the
d. Acetylene belongs to the class of alkynes with presence of HgSO4, the major product is
molecular formula CnH2n-2 a. Propanal
79.Which is the most suitable reagent among the b. Propyl hydrogen sulphate
following to distinguish compound (iii) from c. Acetone
rest of the compounds d. Propanol
i. CH3–C C – CH3 88.When treated with ammoniacal cuprous
ii. CH3 – CH2 – CH2 – CH3 chloride, which one among the following forms
iii. CH3 – CH2 – C  CH copper derivative
iv. CH3 – CH = CH2 a. C2H6 b. C2H4
a. Bromine in carbon tetrachloride c. C2H2 d. C6H6
b. Bromine in acetic acid
89. Ozonolysis of acetylene gives
c. Alkaline KMnO4
d. Ammoniacal silver nitrate reagent a. Glycol b. Glyoxal,formic acid
c. Formaldehyde d. None
80. By coaltar distillation, which is not obtained
90. When acetylene is passed into dilute sulphuric
a. Light oil b. Middle oil
c. Heavy oil d. Mobil oil acid containing Hg2+ ions, the product formed is
a. Acetone b. Acetic acid
81. Which of the following will be the final product
c. Acetaldehyde d. Formaldehyde
when C2H2 reacts with HCl
91.Which of these will not react with acetylene
R – CH2 – CCl2 – R ReagentR – C  C – R
a. NaOH b. Ammonical AgNO3
c. Na d. Hcl
a. b.
92. Which of the following reactions will yield 2, 2-
c. d. None of these dibromopropane
a. HC  CH + 2HBr →
82.The reagent is
b. CH3C  CH + 2HBr →
a. Na b. HCl and H2O c. CH3CH = CH2 + HBr →
c. KOH in C2H5OH d. Zn d. CH3CH = CHBr + HBr →
83. The compound C 3H4 has a triple bond, which is 93.What is the product when 2-butyne is treated
indicated by its reaction with with liquid NH3 in presence of lithium
a. Bromine water b. Bayer's reagent a. n-butane b. cis-2-bute
c. Fehling solution c. trans-2-butene d. 1-butene
d. Ammonical silver nitrate
94.Addition of HCN to ethyne in presence of
84. Acetylene gives
Ba(CN)2 as catalyst gives
a. White precipitate with AgNO3 and red
a. 1, 1-dicyano ethane
precipitate with Cu2Cl2
b. Ethyl cyanide
b. White precipitate with Cu2Cl2 and red
c. Vinyl cyanide d. Divinyl cyanide
precipitate with AgNO3
c. White precipitate with both the reagents 95.Which of the following give H2 gas with Na
d. Red precipitate with both the reagents a. CH4 b. C2H6
85.The bond length between sp3 hybridised carbon c. C2H4 d. C2H2
atom and other carbon atom is minimum in 96. Which of the following reactions is shown by
a. Propane b. Butane alkynes
c. Propene d. Propyne a. Addition b. Substitution
Target MDS for CEE |347|
 c. Polymerization d. All of these c. NO3- d. NO2
97. Shortest C–C bond length is present in 106.The correct structure of benzene was
a. CH3 – CH2 – CH3 proposed by
b. CH3CH2CH2CH3 a. Faraday b. Davy
c. CH2 = CH – CH = CH2 c. Kekule d. Wohler
d. CH  C – C  CH
107. The bond order of individual carbon-carbon
98.In which of the following, the bond length bonds in benzene is
between hybridized carbon atom and other a. One
carbon atom is minimum b. Two
a. Propyne b. Propene c. Between one and two
c. Butane d. Propane d. One and two, alternately
99. What happens when a mixture of acetylene an 108. Six carbon atoms of benzene are of
hydrogen is passed over heated Lindlar’s a. One type b. Two types
catalyst c. Three types d. Six types
a. Ethane and water are formed 109. On heating a mixture of sodium benzoate and
b. Ethylene is formed sodalime, the following is obtained
c. Acetylene and ethane are formed
a. Toluene b. Phenol
d. None of these
c. Benzene d. Benzoic acid
100. CH  CH HgSO4CH3MgBrP/Br2
110. Benzene vapour mixed with air when passed
a. CH3CH(Br)CH3 b. CH3CH2CH2Br over V2O5 catalyst at 775 K gives
c. CH2=CH-Br d. BrCH=CH-CH3
a. Glyoxal b. Oxalic acid
101.The function of anhydrous AlCl 3 in the c. Maleic anhydride d. Fumaric acid
Friedel-Craft's reaction is to
111. Most common reactions of benzene (aromatic
a. Absorb water hydrocarbon) and its derivatives are
b. Absorb HCl
a. Electrophilic addition reactions
c. To produce electrophile
b. Electrophilic substitution reactions
d. To produce nucleophile
c. Nucleophilic addition reactions
102.Benzene reacts with CH 3 COCl in the presence d. Nucleophilic substitution reactions
of AlCl 3 to give
112.Amongst the following, the compound that can
a. C6H5Cl b. C6H5COCl be most readily sulphonated is
c. C6H5CH3 d. C6H5COCH3
a. Benzene b. Nitrobenzene
103. Chemical name of the insecticide gammexene c. Toluene d. Chlorobenzene
is
113. Which of the following is a hydrocarbon
a. DDT
a. Urea
b. Benzene hexachloride
b. Benzene
c. Chloral
c. Ammonium cyanate
d. Hexachloroethane
d. Phenol
104.The reaction of toluene with chlorine in
114.Aromatic compounds burn with sooty flame
presence of ferric chloride gives predominantly
because
a. Benzoyl chloride b. m-chlorotoluene
a. They have a ring structure of carbon atoms
c. Benzyl chloride d. o- and p-chlorotoluenes
b. They have a relatively high percentage of
105. Attacking or reactive or electrophilic species hydrogen
in nitration of benzene is or In the nitration of c. They have a relatively high percentage of carbon
benzene with concentrated HNO 3 and H2SO4 the d. They resist reaction with oxygen of air
attack on ring is made by
a. NO2- b. NO2+

|348| General Medicine - Loading Dose

115.Among the following statements on the c. Zinc dust and sodium hydroxide
nitration of aromatic compounds, the false one d. Soda lime and copper
is 123. Which of the following yield both alkane and
a. The rate of nitration of benzene is almost the alkene
same as that of hexadeuterobenzene
a. Kolbe’s reaction
b. The rate of nitration of toluene is greater than
b. Williamson’s synthesis
that of benzene
c. Wurtz reaction
c. The rate of nitration of benzene is greater than
d. Sandmeyer reaction
that of hexadeuterobenzene
d. Nitration is an electrophilic substitution 124.When toluene is treated with KMnO 4, what is
reaction produced
116.Three fused benzene rings are found in a. Benzene b. Chlorobenzene
a. Naphthalene b. Anthracene c. Benzaldehyde d. Benzoic acid
c. Phenanthroline d. Triphenyl methane
117.After ozonolysis of benzene (not hydrolysis),
the product is CHALLENGING QUESTIONS
a. Benzene triozonide
1. In the case homologous series of alkanes, which
b. Glyoxal
c. Ethanediol one of the following statements is incorrect
d. All of them a. The members of the series are isomers of each
other
118.C6H6 NHO3X Cl2Y. In the above sequence Y is:
b. The members of the series have similar chemical
a. 1-nitrochloro benzene properties
b. 3-nitrochlorobenzene c. The members of the series have the general
c. 4-nitrochlorobenzene formula CnH2n+2, where n is an integer
d. 1,2-nitrochlorobenzene d. The difference between any two successive
members of the series corresponds to 14 unit of
119. Which one of the following will undergo meta
relative atomic mass
substitution on monochlorination
2. The octane number of a sample of petrol is 40.
a. Ethoxy ethane b. Chlorobenzene
c. Ethyl benzoate d. Phenol It means that its knocking property is equal to
the mixture of
120. Hydrocarbon C6H6 decolourise Br2 water and
a. 40% n-heptane + 60% iso-octane
gives ppt. with ammonical AgNO 3 Hydrocarbon
b. 40% petrol + 60% iso-octane
can be
c. 60% n-heptane + 40% iso-octane
a. 1, 3, 5 Cyclohexatriene d. 60% petrol + 40% iso-octane
b. 1, 5 Hexadiyne
3. Formation of 2-butene as major product by
c. 2, 4 Hexadiyne
d. None dehydration of 2-butanol is according to
a. Markownikoff rule
121. Decreasing order of C-C bond length is
b. Saytzeff rule
[JEE Orissa 2004] c. Peroxide effect
(I) C2H4 (II) C2H2 d. Anti-Markownikoff rule
(III) C6H6 (IV) C2H6 4. Which of the following is Friedel-Craft's
a. IV > III > I > II b. I > II > IV > III reaction
c. II > I > IV > III d. IV > I > III > II a. C6H6 + FeCl3 + Cl2 → C6H5Cl
122.Benzene can be obtained by heating either b. C6H5CHO + CH3CHO + KOH → C6H5CH = CH – CHO
benzoic acid with X or phenol with Y. X and Y c. C6H6 + CH3COCl + AlCl3 → C6H5 – CH3
are respectively d. C6H5OH + cHCl3 + KOH → Salicylaldehyde
a. Zinc dust and soda lime 5. CaC2 + H2O → A H2SO4/HgSO4B. Identify A and B
b. Soda lime and zinc dust in the given reaction

Target MDS for CEE |349|

 a. C2H2 and CH3CHO 7. Identify Z in the following series
b. CH4 and HCOOH CH2 = CH2 HBrX HydrolysisY Na2CO3Z
c. C2H4 and CH3COOH a. C2H5I b. C2H5OH
d. C2H2 and CH3COOH c. CHI3 d. CH3CHO
6. In presence of light toluene on reaction with 8. CH  CH + HBr → X, product X is:
chlorine gives
a. Ethylene bromide
a. Benzoyl chloride c. Bromo ethane
b. Ortho chlorotoluene b. Vinyl bromide
c. Para chloro toluene d. Ethyledine bromide
d. Benzyl chloride

Vapour solutions
Answers
1.a 2.a 3.a 4.a 5.a Probable Solutions
6.b 7.b 8.b 9.a 10.a
11.d 12.a 13.a 14.c 15.a 1.(d) Terminal alkane on reductive ozonolysis gives
16.b 17.? 18.c 19.d 20.d methanol.
21.c 22.d 23.c 24.b 25.?
2.(b) (4) Soys dehydration for dehydration there must
26.c 27.b 28.d 29.b 30.c
31.d 32.b 33.? 34.a 35.a be water molecule removed. In reaction there is no
36.d 37.b 38.b 39.c 40.c water molecule involved. So, eliminate (4). And all
42.d 43.d 44.b 45.b options with (4) in it, Hence b.
46.d 47.c 48.c 49.? 50.d
51.d 52.b 53.c 54.b 55.a
3.(a) H–C  C – H
56.c 57.c 58.d 59.a 60.d  10  and 3K bonds
61.b 62.b 63.b 64.a 65.c
4.(b) Use of Lind/or catalyst give Cis. alkene
66.b
5.(b) Electrophilic addition is the characteristics
Probable solutions reaction of benzene. The electrophile generated
Answers here is Cl¯ (Chloranium ion).
1.d 2.b 3.a 4.b 5.b 6.(c) Ozonalysed product adds up to give the original
6.c 7.d 8.b 9.a 10.a reactions.
11.c 12.b 13.b 14.b 15.b
CH3 C = O + O = CCH3 CH3 C = CCH3
16.b 17.a 18.d 19.c 20.a
21.a 22.d 23.d 24.d 25.d HClCH3
26.a 27.c 28.c 29.a 30.a (Addition of HCl occurs according to
31.b 32.c 33.b 34.a 35.b
36.c 37.c 38.b 39.d 40.b
Markovnikov's rule)
41.b 42.c 43.a 44.d 45.c 7.(d) Wurtz reaction double the c-atom in the product as
46.a 47.a 48.c 49.d 50.b compared to reactant,. So, the only possible answer
51.c 52.b 53.d 54.c 55.c
is CH4
56.d 57.d 58.c 59.c 60.b
61.b 62.c 63.c 64.b 65.b 8.(b), 9.(a)
66.b 67.b 68.c 69.a 70.a 10.(a)According the Wurtz reaction
71.d 72.a 73.a 74.c 75.b
76.c 77.c 78.a 79.d 80.d  CH3 CH2 CH2 Br + 2Na etherCH3(CH2)4CH3 + 2NaBr
81.b 82.c 83.d 84.a 85.d 11.(c) Pb(C2H5)4 D1b + 4CH3CH2
86.c 87.c 88.c 89.b 90.c
91.a 92.b 93.c 94.c 95.d + Pb  CH2 = CH2+ Pb Br2
96.d 97.d 98.a 99.b 100.a 12.(b)
101.c 102.d 103.b 104.d 105.b
13.(b)With elevated amount of Grignard's reagent, acetyl
106.c 107.c 108.a 109.c 110.c
111.b 112.c 113.b 114.c 115.c chloride forms ketones
116.b 117.a 118.b 119.c 120.d CH3COCl + MgCH3  CH3COCH3 + Mg 
121.a 122.b 123.a 124.d
14.(b), 15.(b)
|350| General Medicine - Loading Dose
16.(b)Ethane is a saturated compound it can not be 36.(c)
catalytically hydrogenated. 37.(c) In C2H6, C–C bond length is 154 A°.
17.(a) 38.(b)CH3COONa + NaOH CH4 + Na2CO3
18.(d)CH4 Cl2CH3Cl Cl2CH2Cl2 Cl2 CHCl3 Cl2 CCl4 39.(d)Propane is a saturated compound . Ozonide is
Since this reaction takes place by free radical formed only by alkenes or alkynes.
methanism. Hence there is possibility of formation 40.(b)
of ethane. H3–CH–CH2–CH3 + Br2  H3C–\o\al(C – CH2 –
CH3 → CH3–CH3 CH3
19.(c) 41.(b)
20.(a) 42.(c) C2H6Cl + H2 Pd/cC2H6 + HCl
C2H5 O H + CH3 MgBr → CH4 + Mg This reaction is used for the proportion of pure
alkanes.

21.(a) CH32 + 2H Zn/HClCH4 + H2 43.(a)Ag–C  C –Ag + 2HCl → CH  CH + 2AgCl

CH3Z 2Na + ZCH3 DryCH3 – CH3 + 2NaZ 44.(d) CH3COONa + NaOH CaOCH4 + HZ
22.(d) Al4C3 + 6H2O  3CH4 + 2Al2O3
23.(d) 45.(c)
2CH3cOONa + 2H2O ElectrolysisCH3 – CH3 + 2CO2 + 2NaOH + H2 46.(a)CH2 = CH2 + Br2 CCl4
24.(d) 47.(a)CH3–CH2–OH con. H2SO4CH2 = CH2 + H2O
25.(d)CH3 – CH2–Cl + KOH CH2 = CH2 + KCl + H2O 48.(c), 50.(b)
26.(a) 51.(c)
n-hexane because it is linear therefore strong Vander CH3–CH = CH – CH3 + HBr PeroxideCH3–CH2–CH3
Waal's force Anti-markonikov's rule is not applicable to alkenes
27.(c) 52.(b)
2CH3COK + 2H2O ElectrolysisCH3–CH3 + 2CO2 + 2KOH + H2 CH3 –CH = CH2 + H2O conc. H2SO4CH3–\o\al(CH – CH3
28.(c) 53.(d), 54.(c)
CH3 – CH2–Br C2H5ON7CH3 – CH = CH2 + HBr 55.(c)
29.(a)Free rotation around carbon-carbon bond takes CH3CH2I + KOH (role) → CH2 = CH2 + KI + H2O
place easily in alkenes. New ethane and both are CH2 = CH2 + KMnO4H2O\o\al(CH2–+ MnO2
alkanes. But in hexachloroethane both are alkanes.
56.(d)
But in hexachloroethane bulky chlorine atom
CH3 –CH2 – Br + KOH CH2 = CH2+ KBr + H2O
hindess the rotation. Therefore least hindered
rotation takes place in ethane. 57.(d)CH2 = CH2 cold. alc. MnO4\o\al(CH2–
30.(a)Hydrocarbon on complete oxidation produce CO2 58.(c), 59.(c), 60.(b)
and water 61.(b)
CH3–CH3 + 3O2 → 2CO2 + 3H2O 3R–CH = CH2 + B2H6 Dry3R –CH2–CH2OH
31.(b) CH3–CH3 Product is formed according to Anti-Markovnikov's
Replacable hydrogen atom are present only on 4 rule.
primary carbon atoms, Hence, it gives only 62.(c)
monochlore substituted product. CH3 – CH – CH3 (i) Cl3CH3CaCH3+ CHOCH3
32.(c) Chlorination of alkane in photochemical reaction 63.(c) CH3CH2OH conc.CH2 = CH2 + H2O
which takes place by free radical mechanism. Free 64.(b)
radicals are formed by homolysis. CH3–CH2–Clalc.KOHCH2=CH2 + KCl + H2O
33.(b) 65.(b)
34.(a) CH3CH2CH2Br + KOHC2H5OHCH3CH = CH2 + KBr + H2O
35.(b)CH3CH2CH2CH3AlCl3 CH3–\o\al(CH – CH3 66.(b), 68.(c), 69.(a)
Target MDS for CEE |351|
70.(a) 81.(b)
CH – CH = CH2 + HBr PeroxideCH3 – CH2–CH2–Br CH  CH + HCl ¾® CH2 = CH – Cl HClCH3–CH Cl
71.(d) 82.(c)
CH3CH2–OH + H2SO4 CH3CH2HSO4 R – CH2–C l2–R KOH + C2H5OHR – C  C–R + 2HCl
72.(a)CH3–CH2–CH = CH2 + Br2 ¾® CH3CH2 The reaction is an example of dehydrogenation. Hence
73.(a) alcoholic KOH is used as reagent.
74.(c)
75.(b)According to Markovnikov's rule, the negative part 83.(d)
of the unsymmetrical reagent adds to less CH3–C C–H + AgNO3¾® CH3–CC–Ag
hydrogenated (more substituted) carbon atom of 84.(a), 85.(d)
the double bond.
86.(c)
76.(c) CaCl2 + 2H2O → Ca(OH)2 + C2H2
CH = CH + HCl HgCl2CH2 = CH – Cl
CH  CH + 2 [Ag (NH3)2]OH ¾® Ag–C  C– Ag + 87.(c)
4NH3
77.(c) CH3–COOH LiAlH4CH3 – CH2 – OH H+ CH2 = CH2 Br2
CH3 – C  CH + H2O CH3–CH2
alc CH  CH + 2KBr + 2H2O
RearrangementCH3 – CH3
78.(a), 79.(d), 80.(d)

88.(c), 89.(b), 90.(c) COLUMN BIGRIYO 110.(c)

O
91.(a)Nvoleaphiles and alkalies normally do not react
CHCOOH -H2O CHC
with acetylene. Thus NaOH does not react. 9 V2O5
+ O -H2O
2 2 CHCOOH
92.(b) CHC

93.(c) Reduction of alkynes with liquid NH3/Li gives O

alkenes. Maleic anhydride

94.(c)
CH  CH + HCn Ba(CN)2CH2 = CH – C  N
95.(d)CH  CH + 2Na liq.NH3can  can 111.(b), 112.(c)
96.(d) 113.(b)Benzeme (C6H3) is made up of hydrogen and
97.(d) carbon only.
98.(a)We know that C–C bond length = 1.54 A°, C = C 114.(c)They have a relatively high percentage of carbon.
bond length = 1.34A° and C C bond length = 115.(c), 116.(b), 117.(a)
1.20A°. Since propyne has triple bond, therefore it 118.(b)
has minimum bond length. NO3 NO3

99.(b), 100.(a), 101.(c)

102.(d) HNO3 Cl2
COCH3 H2SO4 FeCl2
Cl

Anhydrous
119.(c)
AlCl3 –COOH group so meta directing group hence, ethyl
Benzene Acetophenone benzoate undergo meta substitution.
COOC2H5
103.(b), 104.(d)
105.(b)
(Ethyl benzoate)
HO – NO2 + H+ SO4¯ → H2O + NO2+ + HSO4¯
106.(c), 107.(c), 108.(a), 109.(c)
120.(d)
|352| General Medicine - Loading Dose
121.(a) Bond length 
Bond order is highest for C2H6 so it has minimum
bond strength.
122.(b) (C6H5COOH + NaOH ¾® C6H5COONa + H2O
NaOHC6H6 + Na2CO3
C6H5OH + Zn ¾® C6H6 + ZnO
123.(a), 124.(d)

Challenging solutions
1.(a) The difference between any two successive
members of the homologous series–CH3– i.e. the
molecular weight of every two adjaceve members
by (CH2 = 12+2=14)
2.(c) Octane number of fuel is the percentage iso-octane
in mixture.
3.(b) CH3 – CH2–CH3 CH3–CH = CH – CH3
4.(c) Friedel-craft's reaction
CH3COCl+ C6H6AnhydrousCH3COC6H5+ HCl
5.(a) Wahler reaction
CaC2 + 2H2O  C2H2 + Ca(OH)2
C2 H2dil.H2SO4/HgSO4[CH2 = CHOH]→ CH2CHO
6.(d) Sidechain chlorination and bromination is
favoured by high temperature, light and in absence
of halogen carrier.
C6H5CH3Cl2C6H5CH2ClCl2C6H5CHCl2Cl2C6H5CHCl3Cl2
C6H5CCl3
7.(c) CH2 = CH2 HBrCH3–CH2–Br HydrolysisCH3–CH2OH
Na2CO3CHl3
8.(b) CH  CH+ HBr  CH = CH Br

Target MDS for CEE |353|