Final Hydrocarbon Sheet PDF

IIT-JEE ChEmistry by N.J.
sir ORGANIC chemistry
Hydrocarbon (i) =CH2

H / Pt

2
Alkanes
CH 3
Alkanes  Saturated hydrocarbons.
D / Pt
Methods of preparation (h) 
2
1. Hydrogenation of alkene
Sebatier Sendrens Reaction CH3
H2/Ni, Pt, Pd
CH3 – CH = CH2
H2 / Pt
CH2 
(j)
NH2–NH2/H2O2
CH3
Important : (k) H D2/Pt
D
1) Unsaturation between like atoms wil reduce
C = C, N = N CH = CH2
IR
2) Both H atoms will be attached from same
side (Syn-addition) O OH
3) Less stable & less sterically crowded will LiA/H4
undergo reduction at faster rate. Important :
H/
2 Pd
Q.1 Compare the rate of hydrogenation –C O
l
H2/Ni OH
.S
(a)
H CH3
CH3 H Pd–C is used for selectie reduction of

(b) C=O
alkene, but it cannot reduce
O
H2/Pd–C
Q.3 Ph – CH = CH – C – CH 3
.J
(c)
H2/Ni
Q.4 + H2 Ni
Q.2 Major prduct of reaction
O
N
H2(1eq) CH3 H2/Ni

H2(1eq) Q.5 H2/Pd–C Q.6 C=O
(a) (b)
Ni Pt et
H (1eq)
(c) CH2  CH  CH  CH2  2
 Pd/BaSO
Ni
Q.7 4
CH3 – C  C – CH3 
D / Pt
(d) 
2
Na /NH
Q.8 3
CH3  C  C  CH3 
D2 / Pt
(e) 
R
H2 / Pt
(f)  Na/NH3
Q.9 Na/NH3 Q.10
H2 /(Pt)
(g)   (R = activating)
1
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R
2. CH2 – MgBr + D 2O
Na/NH3
Q.11
6. From aldehydes & ketones
(R = deactivating)
2. From alkyl halides
O
(a) Wurtz Reaction Zn – Hg/HCl
ether Ph – C – CH 3
R  x  2Na  x  R  R  R
Cl Cl O
Na / ether NH2–NH2
(1)   Ph – C – CH 3
Cl KOH
Na / ether
(2) 
Cl CH 2– SH
O H 2 /Ni
CH 2– SH Ph – C – CH 3
(b) Corey House Reaction :
R2CuLi + R'–Cl  R – R '
Q.12 Write the steps for preparation of following O
alkane by corey house reaction ? 2CH 3– SH H2 /Ni
IR
Ph – C – CH 3
(a) (b)
CH 2– OH
(c) CH3 (d) CH2–CH3 O
CH 2– OH Protection
3. From HI/ Red P Ph – C – CH 3
in basic medium
O
R–X R– C – OH
alkanes O
R – OH
.S R – CH = CH2
Q.1 Convert
R – C– H C–H C—H
O O O
O O CH3
R1 – C – R2 O
Q.2 C–O Et
O
4. From carboxylic acids
(a) Soda lime decarboxylation O
O
.J
NaOH R – H Q.3
R – C – OH
CaO/
(b) Kolbe" Electrolysis O
O
O Important
NaOH R – R+ CO2 + H2 1. Al4C3 + H2O  Al(OH)3 + CH4
R – C – OH
N
Electrolysis 2. Be2C + H2O  Be(OH)2 + CH4

anode cathode
COOH NaOH 3. CaC2 + H2O Ca(OH)2 + CH  CH
Q.1
electrolysis
COOH
Properties of alkanes
NaOH
Q.2 Halogenation
electrolysis X X
COOH R – H  h
R  H  H  X
NaOH
Q.3 CH2–COOH electrolysis
Cl
NaOH Q.1 
2
h
 ...... {R1° : R2° : R3° = 1 : 4 : 5}
Q.4 CH 3–COOH electrolysis
NBS
(No. of gases produced at anode) Q.2  
5. Grignard Reagent
1. MgBr + H2O
2
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Mechanism.
Alkene Ph
Ph
Methods of preparation –O +P
O Ph
(1) from alkynes – + Ph
:
H2 /PdBaSO4 C + CH2 — P — Ph R1 — C — CH2
R1 — C  C — R2   R1 R2
Ph R2
H2 — Pd — BaSO4 (Rosenmund’s Catalyst)
H2 — Pb — CaCO3 (Lindlar’s catalyst.
Syn – addition  cis alkene is produced. Ph
R1 O Ph
Imp. Reactivity of alkyne is more than alkene C P
towards hydrogenation. R2 CH2 Ph
(2) Dehydration of alcohol (E1) Ph

R1
C = CH2 + O = P — Ph
Conc.H SO R2
OH 
2 4
 Ph
(170C)
1. P(PH3 ) O
Q.1 CH3 — Cl   (A) (B)
IR
2. CH3Li
Al2O3 Conc.H2SO4

   
(170C)
(E2 ) OH (E )
1 Ph
C=O
1. P(PH3 )
Q.2 Cl   (A) CH3 (B)
2. CH3Li
O
(3) Dehydrohalogenation:- 1. P(PH3 )
H
.S
alc.KOH 
Q.3
Cl

2. CH3Li
 (A) (B)
CH3 — C — CH2 


(E2 ) (5) Kolbe Electrolysis
CH3 Cl
CH2 — COOK
electrolysis
Q.1  
O— / OH 


|
CH2 — COOK
 - - - - - - - - -
.J
Cl (6) NaI/Acetone
Br
Q.2 alc.KOH 
 NaI  - - - - - - - - - -
 CH2 — CH2 
Acetone
Br
Cl Remember.
N
NaI  R — I  NaBr 
R — Br 
Acetone  (Finkelstein Reaction)
alc.KOH  NaI  R — I  NaBr 
R — Cl 
Q.3 —CH2 — CH — CH3  Acetone 

Cl
(4) Wittig Reaction Q.1 NaI  (A)


Br Acetone
Ph
R1 Br
C = O + CH2 = P — Ph - - - - - - - - - -
R2
 Ph (7) Zn - dust
Zn dust
CH3—CH — CH — CH3  - - -
Br Br
3
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Br Br
Zn dust
CH3 — CH  - - - - - - - - - - CH3 Br
Br Zn dust
Q.12 
Br CH3 H
Zn dust H
Q.1   Reaction of Alkene
Br 1. Markownikoff addition
Br Zn dust (a) HBr 

Q.2 Br  CCl4
Br H /H2O
Zn dust (b)  
Q.3 
Br H+/R
O
H
Br (c)
Ph
Br NaI  2. Anti – Markonikov addition
Q.4 
Acetone HBr
IR
CH3 — CH = CH2  
Br R–O–O–R
HBr
 
Q.5 O + (Ph)3P = CH — CH3  R–O–O–R
COOK 3. Halogenation
electrolysis
Q.6  X2
COOK   ----------
.S C=C CCl4
1. CH3 I
Q.7   Br2
2. Ag2O   ----------
NH2 3.  CCl4
1. CH3 I 4. Halohydrin
Q.8  
2. Ag2O HOCl 
N 3.  CH3 = CH — CH3  ------
.J
H HOBr 
 ----------
1. CH3 I 5. Hydrogenation
Q.9  
2. Ag2O H2 /Ni
N 3.  C=C   ----------
CH3
N
H Br 6. Diel’s Alder Reaction

Zn dust
Q.10 
Br H
+ ||  ------
CH3
CH3
Ph H
alc. KOH
Q.11 
Ph Br 1. +  - - - - - - - - - -
CH3
2. +  - - - - - - - - - -
4
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OZONOLYSIS:-
1. O3
3. + - - - - - - - - - - C=C  - - - - - - - - - -
2. Zn/H2O
R3 R2 1. O3
C=C ----------
7. Reaction with carbene 2. H O H
CH2N2 H R1
1. CH3 — HC = CH2  ----------
h
CHCl3 1. O3
2. CH3 — CH = CH — CH3  ------  - - - - - - - - - -
KOH 2. Zn/H2O
CHCl3
3.  ---------- Reaction of alkene (Hydroxylation)
KOH
8. OMDM (oxymercuration – demercuration) CH3 CH3

alk. KMnOH
1. C=C  - - - - -
1. Hg(OAC)2 H O H
CH3 — CH = CH2 ---- H
IR
H
2. NaBH4 alk. KMnO4
Mechanism:-   ------
S–
H
CH3 — CH = CH2 + Hg — O — AC CH3 — CH — CH2 + :O:
H O
CH3 CH3
Hg—OAC R—C—O—O—H
2. C=C
OH
.S H + H
O
H H
H /H2O
- - - - - - - - - -   - - - - - - - - - -
CH3— CH — CH2 CH3— CH — CH2
Hg—O—C—CH3 Hg—OAC
– O
:
H O
OH
O R—C—O—O—H
—
CH3— CH — CH2 + Hg + O — C — CH3
.J
O/Ag
2
1. Hg(OAC)2 R O H
Q.1
2. NaBH4 NBS
1. NBS 

1. Hg(OAC)2 R O H
Q.2
N
2. NaBH4 NBS 
2. 
+
H /H2O
3. NBS 

1. Hg(OAC) 2 R O H
Q.3
2. NaBH4
5
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ALKYNES
Preparation of alkynes 4. Tetra halides
1. Intermolecular Kolbe Electrolysis:– Br Br
CH — COOK Zn dust
|| electrolysis CH3 — C — C — CH3 
 

CH — COOK Br Br
2. Vicinal dihalides Ag
5. CH I3  
2NaNH Powder
2
CH3 — CH — CH — CH3 
E2
 6.
Br Br 7. 6. CaC2 2H2O 
3. Gem dihalides Conversion of terminal to non – terminal alkyne

Br CH3 — CH2 — C  CH
alc.KOH
2NaNH2 NaNH2
CH3 — CH2 — C — CH3  
(n – hexane or paraffin solvent)
IR
Br
(1) Forward Reaction:–

.. O
CH3 — CH2 — C  CH + OH CH3 — CH — C  CH + H H
..
.S CH3 — HC = C = CH
H
O
H

CH3 — HC = C = CH2 + OH

OH
. . H
CH3 — C = C = CH2 + O
H
.J
. .
CH2 — C  C — CH2
O
H H

CH3 — C  C — CH3 + OH
driving force is thermodynamic stability.
N
(2) Reverse Reaction:–

..  
CH3 — C  C — CH3 + NH2 CH3— C  CH2 : + NH3
. .
CH3 — C  C = CH2
NH3
.. 
CH3 — CH = C = CH2 + NH2
.. 
NH2
CH3 — CH = C = CH:  + NH3
. .
CH3 — CH — C  CH
NH3
6
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.. 
CH3 — CH2 — C  CH + NH2
NaNH2
 
CH3 — CH2 — C  C: Na (ppt.)
 driving force of reaction is insoluble salt of alkyne.
Acidic nature
R - OH > CH  CH > NH3
Reaction of alkynes
(1) Hydration
O
HgSO4
CH3 — C  CH   CH3 — C — CH3
H2SO4
Mechanism
. .
CH3 — C  CH + Hg+2  CH3—C=CH (Complex form more reactive towards Nu )
IR
Hg+2
O
H H
H + H
O
CH3—C=CH
.S Hg
+1
OH O
+2
CH3—C=CH2 + Hg (enol-keto Tautomer) CH3–C–CH3
Q. Identify major product:–

HgSO4 O
.J
(1) Ph — C  C — CH3  
dil.H2SO4
C Hg2
CH 
HgSO4 (6) 
(2) CH3 —CH2 — C  CH   H2SO4
dil.H2SO4
Br2 HgSO4
(3) Ph — CH = CH2   (7) CH3 — C  CH  
CCl4 D2SO4
N
2NaNH2 HgSO4
(A)   (B)   (C) Polymerisation of alkynes
H2SO4
(4) CH3 — O C  C (1) CH  CH + 

HgSO4
  Red Hot Cu
H2SO4
CH CH
C CH CH CH  
(5) HgSO4 (A) NH2 NH2 / OH CH CH

    (B)
H2SO4 Red Hot
(2) CH3 — C  CH 
Cu
Zn–Hg/HCl
(C)
7
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CH CH
||| ||| Cu  5. C  C — CH3 H /ROH 

(3) 

CH CH
S

NH4OH/ AgNO3 CH C : Ag + (white ppt.)
Nucleophilic addition (exceptional)
(4) 2CHCH  
ammonical Cu2Cl2 H— C C : Cu+ (red ppt.) 1.

Test for alkenes & alkynes
–
:
Nu –
:
CH3—C C—CH2—CH3 CH3—C =C—CH2—CH3
Alkenes
1. decolourise Br2/H2O. Nu
Cold  +
2.  E
alk. E Nu – E
:
K MnOH Nu
CH3—C—C—CH2—CH3 CH3—C = C—CH2—CH3
:
Alkynes –
Nu Nu
ammonical
IR
AgNO3 +
1. CH3 — C  CH  E
Ag (NH3 )2
2. ammonical
CH3 — C  C — CH3  E Nu
AgNO3
CH3—C—C—CH2—CH3
3. decolourise Br2/H2O. E Nu
Cu2O
4. 2 CH3 — C  CH
.S  
Since carbanion is stable on Sp carbon atom but
Electrophilic addition these type of reactions not given by alkenes.
HBr OH/H2O
1. CH3 — C  CH  1. CH3 — C  C—CH3  
Br2 / CCl4
2. CH3 — C  C—CH3 
2. CH3 — C  C—CH3 RO /ROH 

.J
HCl/CCl4 O O
3. CH3 — C  C—CH3   –
R–C–O R–C–OH
3. CH3 — C  C—CH3
H /H2SO4
4. CH3 — C  C—CH3  
HgSO4
N
8
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IIT-JEE ChEmistry by N.J. sir ORGANIC chemistry
DPP NO-01 Time: 15 minutes
CLEMMENSEN REDUCTION:- O
The reduction of carbonyl groups of C—CH=C—OH
aldehydes and ketones to methylene groups Zn(Hg)
with amalgamated zinc and concentrated Q.8 O  
HCl
hydrochloric acid is known as Clemmensen
reduction. The mechanism summarized
C2H5
below showing that reduction under acidic
conditions often involves protonated species
to which the metal offers. Zn(Hg)
Q.9  
O HCl
Zn(Hg) or Na(Hg)
C2H5 — C — CH3   O
HCl
C2H5 — CH2 — CH3 O
IR
MECHANISM OR CLEMMENSEN REDUCTION:- Zn/Hg,C2H5OH
 Q.10  
O

OH OH HCl,24h
H Zn
2+
Zn
C2H5—C—CH3 C2H5—C—CH3 +2e
C2H5—C—CH3
CH3
H—Cl
H  H Zn,Hg
O OH Q.11 Me(CH2)5 CH = O 
 25%HCl
C2H5—CH—CH3
Zn
2+
Zn + 2e

–H2O
.S
C2H5—CH—CH3 H C H —CH—CH
2 5 3
Q.12 EXCEPTION OF CLEMMENSON:-

(i) Diketo containing active methylene group
C2H5—CH—CH3
H—Cl
C2H5—CH2—CH3+ZnCl2 when undergoes clemmenson reduction,
unexpected product are formed.
Zn/Hg O O
Q.1 PhCOCH2 – CH2COH 
HCl
OH Zn (Hg)
CH3 — C —CH2— C —CH3  
CHO
HCl
O
.J
ZnHg
Q.2  
HCl CH3— C — CH — CH3
Zn/Hg CH3
Q.3 O 
HCl
O MECHANISM:-
N
Zn(Hg)
Q.4 Ph — C — CH3   O O O O
HCl
O = C — CH 3 CH3—C—CH2—C—CH3 CH3—C—CH2—C—CH3
O O
Zn(Hg) 2e H—Cl
Q.5  
HCl
NO2 O O
O = C — CH 3 2e HCl
HCl
Zn(Hg) OH OH
Q.6   (A)
HCl
Zn(Hg)
O Example  
HCl
Zn(Hg) O O
Q.7 
HCl,H2O
9
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IIT-JEE ChEmistry by N.J. Sir ORGANIC chemistry
MOZINGO METHOD:-
CH2 SH
O| R S R S R H
CH2 SH Raney Ni
(i) R — C   C (ii) C   C
H H2 /Ni
H S H S H H
H
Cyclic thioacetal de-sulfurisation

MECHANISM OF MOZINGO METHOD:-

Protonation in acidic medium increases electrophilicity.
O O–H
+ 
H H
R—C—H R—C H — S — CH2 — CH2 — S — H 
IR
H
OH H OH
R — CH — S — CH2 — CH2 — SH  R — CH — S — CH2 — CH2 — SH 
H
H
S H CH2
H CH2
O H CH 2 S
.S
R — CH — S — CH2 — CH2 — SH  R — CH = S — CH 2  R — CH S 
H
H2 / Ni
S S   R — CH3
R — CH
Imp. Raney Nickel  H2 molecule is adsorbed on

Ni. Conversion:
.J
O
O O OH
+H CH3
SH SH
(i) Raney—Ni
(ii) SH SH
Raney—Ni O
(i)  O
C—H C—H
O
OH
(i) HS SH, BF3
N
(iii) (ii) Raney—Ni C—OEt O C—Ph

O
O (ii) 
O Ph
MeO O
H H NNH , 
(iv) 2
 2
triethylene (iii) CH3 — C — CH2 — CH2 — CHO 
glycol,KOH
MeO OH
CH3 —C— CH2CH2CHO
Protecting Groups:
R HO — CH2 R O CH
C = O+  C
H HO — CH2 H O
cyclic-acetal
Glycol is used for protection of aldehyde and
Ketone.
10
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WITTING REACTION O
Witting reaction is the substitution of a C = C bond (C) H — C — H + H2C = PPh3 
for a C = O bond. (D) All
The witting reaction is a reaction between a Q.3 Witting reaction is used for preparation of:
carbonyl compound (aldehyde or ketone
(A) Alkene (B) Ketone
only) and a species known as a
phosphonium ylid. An ylid is a species with (C) Aldehyde (D) Acid.
positive and negative charges on adjacent
atoms, and a phosphonium ylid carries its Q.4 Give the structure of he alkene(s) formed in
positive charge on Phosphorus, each of the following reactions.
phosphonium ylids are made from
Ph3P butyllithium
phosphonium salts by deprotonating them (A) CH3CH2I    
with a strong base. acetone 

IR
R R
R Ph3P butyllithium
(B) CH3Br    
P: CH 3—I  P — CH3 I
R benzaldehyde
R  
R
O
CH3 CH2 Give the product of the following reaction:
Base +
P
.S
  P
R R R R R R Q.5 O + CH2 = PPh3 
R
R R R 3P
P Q.6 O + CH2 = PPh3 
O O
R R H
R—P O
+   
.J
O
Triphenyl Phosphineoxide Q.7 + CH2 = PPh3   
O
 
Q.1 + H2 C  PPh3  (A) Q.8 + CH2 = PPh3 
N
product (A) is O
O
(A) (B) (C) (D)
Q.9 H + CH2 = PPh3  
Q.2 In which of the following Geometrical isomer
O
is formed as a products.
Q.10 + CH2=PPh3 
(A) CH3 — CH = O + H2C = PPh3 
(B) CH3—CH = O + CH3 — CH = PPh3  O
11
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OXYMERCURATION-DEMERCURATION (OMDM):-
OMDM is a hydration process of alkene according to Markawnikoff's rule with no rearrangement of
cyclic mercuinium ion. In oxymercuration, the alkene is treated with mercuric acetate in aqueous
tetrahydrofuran (THF). When reaction with that reagent in complete, sodium borohydride and
hydroxide ion are added to the reaction mixture.
(i) Hg(OAc)2,H2O,THF
R — CH = CH2   R — CH — CH3
(ii) NaBH4,HO—
OH
AcO— = CH3COO—
MECHANISM FOR OXYMERCURATION:

OAc
IR
OAc Hg +
H2O:
CH3CH = CH2 + Hg — OAc CH3CH — CH2 CH3CHCH 2—Hg—OAc
:
+
OH
+ AcO—
H
.S —
OAc
CH3CHCH2—Hg—OAc
OH + AcOH
O
Q.1 Identify the product of the following
reaction:- OH
(i)Hg(OAc)2,H2O
(v)  
.J
(ii)NaBH4 ,OH
CH3
C CH
(i) (i)Hg(CF2COO)2,CH3OH
 
(ii)NaBH4,OH— (i)Hg(OAc)2,H2O
(vi)  
(ii)NaBH4 ,OH
N
(i)Hg(OCOCH3 )CH3OH
(ii)  
(ii)NaBH4 ,OH
Q.2 How could each of the following compounds
be synthesized from an alkene by OMDM?
(i)Hg(OAc)2,H2O OH OCH2CH3
(iii)  
(ii)NaBH4 ,OH
(i) (ii)
(i)Hg(OAc)2,H2O
(iv)   CH3 CH3
(ii)NaBH4 ,OH
(iii) CH3CCH2CH3 (iv) CH3CCH2CH3
OH OCH3
12
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HYDROBORATION-OXIDATION:-
Hydroboration has been developed by brown as a reaction of tremendous synthetic utility because
alkyl boranes are able to undergo a variety of transformation. Hydroboration is a one step, four
centre, cis addition process in accordance with M. rule but after oxidation it seems to be appear to
violate M. rule.
—
OH ,H2O2,H2O
Hydroboration oxidation CH3CH2CH2OH
(i) BH3 THF CH3COOH
CH3CH2CH3
CH3CH = CH2   (CH3CH2CH2)3B Hydroboration reduction
AgNO3
Dimerisation
CH3CH2CH2
CH3CH2CH2
IR
MECHANISM OF HYDROBORATION:
H H
2
CH3CH=CH2 CH3 — C — C — H CH3CH2CH2 (CH3CH2CH2)3B
.S
H—BH2 H BH2 BH2
an alkylborane
More stable
transition state
Mechanism of oxidation:-
HOOH + HO— 1 HOO— + H2O
R R R R
.J
repeat the two
preceding steps
—
R—B + O—OH R—B— —O—OH R — B — OR two times
RO — B — OR
—
R R — HO
+ OH
OR
RO — B—— OR
N
OH
repeat the two

OR OR
preceding steps
3— two times —
3 ROH + BO3 ROH + RO — B RO + RO — B
O— O—H
Q.1 Identify the product of the following

reaction:- (i)BH3
(i)BH3 (ii)  
(i) CH2 = CH2   (ii)HO ,H2O2,H2O
(ii)HO,H2O2,H2O
13
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BH3 ,THF
(iii)   Q.4 What alkene can be used to prepare each
H2O/OH alcohol as the exclusive product of a two
step hydroboration oxidation sequence?
HO
BH3 ,THF
(iv)  
H2O/OH (A) (B)
OH
(v) BD3,THF OH
CH3COOH
BH3,THF
CH3COOD (C)
BT3,THF
CH3COOD (i) Hg(OAc)2, H2O (A)
C CH (ii) NaBH4
(i)BH3,THF Q.5
(vi)   (i) BH3, THF
(ii)H2O/OH (B)
(ii) H2O2
IR
(i) Hg(OAc) 2, MeOH
(i)BH3 (A) No. of products
(Including stereo)
(vii)   (ii) NaBH4, OH
(ii)H2O2,HO Q.6
(i) BH3, THF
(B) No. of products
(Including stereo)
(ii) H2O 2
(i)BH3
(viii)   (i) BD3, THF
.S (ii)H2O2,HO
(ii) H2O2
(A)
Q.7
(i)BH3 (i) Hg(OAc)2, MeOH
(ix)  
(ii)H2O2,HO (B)
(ii) NaBD4, OH
(i)BH3
(x)  
(ii)H2O2,HO H H
Q.8 OMDM Q.9 OMDM
(i)BH3
.J
(xi)   HBO HBO

(ii)H2O2,HO
Q.2 What alkyl borane is formed from H H

hydroboration of each alkene? Q.10 OMDM Q.11 CH3—C  CH OMDM
HBO HBO
(A) (B)
N
H
(C) (D) Q.12 OMDM
HBO
Q.3 Draw the product formed when each alkene
is treated with BH3 followed by H2O2, HO
include the stereochemistry at all streogenic
centres.
(A) (B)
(C) (D)
14
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EXERCISE – I
Q.1 1-Methylcyclopentene can be converted into the Q.6 Compound (A) on oxidation with hot
given compound KMnO4/ OH gives two compound
D O
CH3 – CH – COOH & CH3 – C – CH2CH2CH3
CH3 CH3
by the use of which of the following regents ? compound A will have structure.
(A) BD3 followed by HCOOH (A) CH3CH2 – C = C – CH2CH3
(B) BH3 followed by HCOOD
(C) BD3 followed by HCOOD CH3 CH3
O (B) CH3 – CH – CH = C – CH2CH2CH3
(D) BH3 followed by D – C – O – H CH3 CH3
(C) CH3CH – C  C –CH3
Q.2 Identify (P) in the following reaction :
H H CH3
Ph
+2 H / H2 O (D) CH3 – CH – C  C – CH – CH3
  (P)
O CH3 CH3
IR
Ph Ph Q.7 Number of required O2 mole for complete
O
(A) (B) combustion of one mole of propane
O O (A) 7 (B) 5 (C) 16 (D) 10
O
Ph O Ph
O Q.8 How much volume of air will be needed for
(C) (D) complete combustion of 10 lit. of ethane
O
O (A) 135 lit. (B) 35 lit.
(C) 175 lit. (D) 205 lit.
Q.3 The reaction of E-2-butene with CH2I2 and Zn –
of
.S
Cu Couple in either medium leads to formation
Q.9 During the preparation of ethane by Kolbe’s
electrolytic method using inert electrodes the pH
CH3 CH3 CH3 H
(A) H (B) H of the electrolyte
H CH3
(A) Increases progressively as the reaction
proceeds
CH3 (B) Decreases progressively as the reaction
CH3 CH3
(C) (D) CH3 proceeds
H H
(C) Remains constant throughout the reaction
(D) May decrease of the concentration of the
.J
Q.4 The reaction of cyclooctyne with HgSO4 in the
presence of aq. H2SO4 gives electrolyte is not very high
OH OH
(A) (B) Q.10 Ethylene forms ethylene chlorohydrin by the
OH OH action of
O (A) Dry HCl gas
(C) (D) (B) Dry chlorine gas
N
(C) Solution of chlorine gas in water

(D) Dilute hydrochloric acid
CH3 H 18

( i ) CH3 COO OH
Q.5     X Q.11 Anti–Markownikoff’s addition of HBr is not

( ii ) H3 O observed in
H CH3 (A)Propene (B) But-2-ene
The probable structure of ‘X’ is (C) Butene (D) Pent-2-ene
CH3 CH3
18 18 Q.12 Which alkene on heating with alkaline KMnO4
H OH H OH solution gives acetone and a gas, which turns
(A) H OH (B) HO H lime water milky
CH3 CH3 (A) 2-Methyl-2-butene (B) Isobutylene
(C) 1-Butene (D) 2-Butene
CH3 CH3 Lindlar Na / NH3

18 Q.13 B   R – C C – R   A
H OH H OH A and B are geometrical isomers
(C) H (D) H 18
OH OH (R – CH = CH – R)–
CH3 CH3 (A) A is trans, B is cis
15
----------------------------------------------------------------------------------------------------
(B) A and B both are cis (C) CH3CH2CHO (both)
(C) A and B both are trans (D) CH3 – C – CH3 (both)
(D) A is cis, B is trans
O
B D6
Q.14 Which is expected to react most readily with Q.21 CH3CH = CH2 2  
 product X
H2O 2 / OH
bromine
(A)CH3CH2CH3 (B) CH2 = CH2 X is
(C) CH CH (D) CH3 – CH = CH2 (A) CH3 – CH – CH2D (B) CH3 – CH – CH2OH
OH D
Q.15 An alkyne C7H12 on reaction with alk. KMnO4 (C) CH3 – CH – CH3 (D) None is correct
and subsequent acidification with HCl yields a
mixture of CH3 – CHCOOH + CH3CH2COOH . OD
CH3 Q.22 Mixture of one mole each of ethene and propyne

The alkyne is on reaction with Na will form H2 gas at S.T.P.
(A) 3-Hexyne (B) 2-Methyl-3-hexyne (A) 22.4 L (B) 11.2 L
(C) 2-Methyl-2-hexyne (D) 2-Methyl-2-hexene (C) 33.6 L (D) 44.8 L
Q.16 A compound (C5H8) reacts with ammonical

AgNO3 to give a white precipitate and reacts with
IR
excess of KMnO4 solution to give (CH3)2CH – reagent R reagent R
Q.23 2 
   1
    
COOH. The compound is HO OH
(A) CH2 = CH – CH = CH – CH3
(B) (CH3)2CH – C  CH
(C) CH3(CH2)2C  CH R1 and R2 are
(D) (CH3)2C = C = CH2 HO OH
(A) Cold alkaline KMnO4, OsO4/H2O2
Q.17 Which of the following reagents cannot be used to
.S
locate the position of triple bond in CH3 –C C – CH3
(B) Cold alkaline KMnO4, HCO3H/ H3 O 
(C) Cold alkaline KMnO4, CH3 – O – O – CH3
(A) Br2 (B) O3 (C) Cu 22  (D) KMnO4 (D) C6H5CO3H, HCO3H
A
Q.18 CH3 – CH2 – C  CH CH3C  C – CH3 A
Q.24 
B 
A and B are A can be
(A) alcoholic KOH and NaNH2 (A) Conc. H2SO4 (B) alcoholic KOH
(B) NaNH2 and alcoholic KOH (C) Et3N (D) t-BuOK
.J
(C) NaNH2 and Lindlar
(D) Lindlar and NaNH2 Q.25 BrCH2 – CH2 – CH2Br reacts with Na in the
presence of ether at 100°C to produce
 (A) BrCH2 – CH = CH2 (B) CH2 = C = CH2
BH3 / THF
Q.19 B   – CH2 H3O
 A (C) CH2 – CH2 (D) All of these
H2 O2 / OH
CH2
(A) Both
N
CH2OH
CH3
(1) Hg( OAc )2 / H2O / THF
(B) Both CH3 Q.26       A.A is
OH ( 2 ) NaBH / NaOH / H O
4 2
(C) CH3OH , CH3 OH

CH3
OH (A) (B)
OH
CH3 , OH
(D) CH2OH
OH CH3
OH CH3
BH3 THF HgSO4 / H2 SO4 (C) (D)
Q.20 B   CH3 – C  CH      A
H2 O2 ,OH
A and B are -
x
O Q.27 CH3  CH  CH  CH3  product is Y (non-
cis
(A)CH3CH2CHO, CH3 – C – CH3 resolvable) then X can be
O (A) Br2 water
(B) CH3 – C – CH3 ,CH3CH2CHO (B) HCO3H/ H3 O 
16
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(C) Cold alkaline KMnO4 O
(D) All of the above (A) CH3 – CCOOH (B) CH3COOH (C)
Q.28 A mixture of CH4, C2H4 and C2H2 gaseous are O
passed through a Wolf bottle containing CH3 – CCHO (D) CH3COOH
ammonical cuprous chloride. The gas coming
out is O CH2 – CH2
(A) Methane
(B) Acetylene Q.33 OH OH CH MgBr
3
    A, A is

(C) Mixture of methane and ethylene H3 O
(D) Original mixture CHO
O H3C OH
Q.29 For the ionic reaction of hydrochloric acid with OH OH
the following alkenes, predict the correct (A) (B)
CH CH
sequence of reactivity as measured by reaction OH CH3
rates : HO CH
3 HO CH
(I) ClCH = CH2 (II) (CH3)2.C = CH2 3
(III) OHC.CH = CH2 (IV) (NC)2C = C(CN)2 O CH3
(A) IV > I > III > II (B) I > IV > II > III (C) (D)
CH
IR
(C) III > II > IV > I (D) II > I > III > IV CHO O CH3
CH3 – C – NH2
EXERCISE – II
Mg / dry ether O
Q.30  (X)
Br     (Y)
The structures of (X) and (Y) respectively are Q.1 An alkene on ozonolysis yields only ethanal.
There is an isomer of this which on ozonolysis
(A) X = MgBr ; Y= OH yields :
(A) propanone (B) ethanal
(B) X =
.S
Br ; Y= OH (C) methanal (D) only propanal
Mg OH Q.2 Aqueous solution of potassium propanoate is

electrolysed. Possible organic products are :
(C) X = MgBr ;Y= (A) n-Butane (B) C2H5COOC2H5
(C) CH3 – CH3 (D) CH2 = CH2
(D) X = BrMg MgBr ; Y = HO OH
H2 / Pt O /H O
Q.3 (A) C4H6   (B) C4H8 3 2
CH3COOH
.J
H2 O,H2SO4 / HgSO4 D O,HgSO / H SO
Q.31B    C  CH 2   
4
2 
4
 Hence A and B are
BH3/THF
H2O2/OH– (A) CH3C  CCH3, CH3CH = CHCH3
C (B) CH2 = CHCH3 = CH2, CH3CH = CHCH3
A, A, B and C are (C) , CH3CH = CHCH3
(A) (D) None
CCHD2 CCH3
O O A
N
Q.4 Ph – C – CH3  Ph – CH2 – CH3

(X) (Y)
O
CH2CHO A could be :
(A) NH2NH2, glycol/OH–
(B) Na(Hg)/conc. HCl
(Z)
(C) Red P/HI
(B) Y, X and Z (C) Y In all cases
(D) CH2 – CH2 ; Raney Ni – H2
(D) Z in all cases
SH SH
Q.32 End product of the following sequence of Q.5 CH2 = CHCH2CH = CH2  NBS
 A, A can be
reaction is

(A) CH2 = CHCHCH = CH2
CH3MgBr CO 2 / H3O
CH  CH       Br
HgSO4 / H2 SO4 Ag2O 
      
   (B) CH2 = CHCH = CH – CH2Br
(C) CH2 = CHCH2CH = CHBr
(D) CH2 = CHCH2C = CH2
Br
17
----------------------------------------------------------------------------------------------------
Q.6 peroxide
Ph – CH = CH2 + BrCCl3   Codes :
Product is : A B C D
(a) 2 1 3 4
H H
(b) 1 2 4 3
(A) Ph CH2CCl 3 (B) Ph CH2Br (c) 1 2 3 4
(d) 2 1 4 3
Br CCl3
Br CCl3
Q.12 List I List II
(C) Ph CH2CCl 3 (D) Ph CH2Br electrolys is
(A) RCOONa    R – R (1) Corey-House
H H reaction
Q.7 Which of the following will give same product
with HBr in presence or absence of peroxide (B) R–CH2–COOH Soda
 lime  R–CH3 (2) Kolbe
(A) Cyclohexene electrolysis
(B) 1-methylcyclohexene
(C) 1,2-dimethylcyclohexene (i ) AgNO3
(C) RCOOH    R – Cl (3) degradation
(D) 1-butene (ii) Cl2 / 
IR
Q.8 The ionic addition of HCl to which of the 
following compounds will produces a compound (D) R’ – X + R2CuLi  R – R’ (4) Hundsdiecker
having Cl on carbon next to terminal. reaction
(A) CF3.(CH2)3.CH = CH2 Codes :
(B) CH3.CH = CH2 A B C D
(C) CF3.CH = CH2 (a) 2 3 4 1
(D) CH3.CH2CH = CH.CH3 (b) 1 3 4 2
Q.9 Which reagent is the most useful for (c) 2 4 3 2
.S
distinguishing compound I from the rest of the
compounds
(d) 2 4 1 3
Q.13 List I List II

CH3CH2C  CH CH3C  CCH3 O
I II
C – CH3 CH2 – CH3
CH3CH2CH2CH3 CH3CH = CH2 (A) (1) Birch
III IV
Cl Cl
(A) alk. KMnO4 (B) Br2/CCl 4
reduction
(C) Br2/CH3COOH (D) Ammonical AgNO3 O
C – CH3 CH2 – CH3
.J
Q.10 List I List II (B) (2) Stephen’s
(A) Walden Inversion (1) Cis addition
OH HO
(B) Recemic mixture (2) Trans addition
reduction
Baeyer
(C) Alkene Re
  (3) SN1 reaction
agent
(C) (3) Wolf-Kishner
Br2
(D) Alkene  (4) SN2 reaction
reduction
Codes :
N
O
A B C D
(D) (4) Clemmensen
(a) 3 4 2 1
(b) 3 4 1 2 reduction
(c) 4 3 1 2
(d) 4 3 2 1
Q.14 Which of the following produce chiral molecule
Q.11 List I List II after treatment with Lindlar’s catalyst ?
(A) CH3 – C  C – CH3  (1) Na/NH3()
cis-2-butene (A) (B)
(B) CH3 – C  C – CH3  (1) H2/Pd/BaSO4
trans-2-butene
(C) CH3 – C  C – CH3  (1) alc. KOH,  (C) (D)
1-Butyne 
(D) CH3 – C  C – CH3  (1) NaNH2, 
2-Butyne

18
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Q.15 Column I Column II O O
Cold dil. KMnO4 CH CH
(A)      (P) Optically inactive Q.5 C = C
due to internal NO2 – CH2 CH2 – NO2
compensation NH2 –NH2 / H2O2
 A. Write the structure of A
   
(B) ( i ) CH3 CO 3H
   (Q) Optically inactive Q.6 Give the structure of the alkene that yields on
( ii ) H3O ozonolysis
due to external (i) CH3CH2CH2CHO & HCHO
compensation (ii) C2H5COCH3 & CH3CH(CH3)CHO
(iii) Only CH3CO.CH3
(iv) CH3.CHO & HCHO & OHC.CH2.CHO
D
(C) 
2
(R) Product has (v) Only OHC – CH2CH2CH2 – CHO
Ni
presence of two chiral Q.7 What are A to K for the following reactions
center ArCH2 Cl
(i) PhC  CH + CH3MgX  A   B
Li / NH
(D) 

Br
2
 (S) Diastereomers will  
3
 C.
IR
H2 O h alcoholic
(ii) PhCH2CH2CH3 + Br2  D   E
KOH
be formed
cold dil. KMnO 4 hot KMnO 4
    F    G
Q.16 Which starting material should be used to
produce the compound shown below ?
H CH3
H (iii)  H3C
HO O Me Me OH OH
O3
?   O OH
Zn– H2O
O
.S (iv) I
(A) (B) OH
HBr
(v) CF3 – CH = CH2  J
Me
(C) (D) NBS

(vi)  K
.J
Me Me
EXERCISE – III
Q.8 Explain the following
Q.1 Give the product of (i) 1, 2 shift does not take place during
BH H 2O 2
oxymericuration demercuration. Why ?
(a) 
3
 A   B (ii) Halogenation of alkene is anti addition but not
THF
N
syn addition. Why ?

COOH H
(iii) Anti markovnikov addition is not applicable
(b) C = C 1. BD THF
 3.  for HCl. Why ?
H COOH –
2. D 2O2 ,DO
(iv) 1, 4–addition takes place in butadi-ene. Why
?
CH3 (v) C – H bond is stronger than C – C bond but in
LiAlH4 chlorination C – H bonds get cleaved but not
Q.2 CH3 – C – Cl    ?
C – C bond. Why ?
CH3
Q.9 The following cyclisation has been observed in
Q.3 What are the ozonlysis product of the oxymercuration & demercuration of this
unsaturated alcohol. Propose a mechanism for
this reaction.
C2H5 C2H5 1.CF CO H
Q.4  
3
3  A + B. What OH
C = C 
2. H2O / H 1.Hg(OAC)
  
2
 O
H H 2.NaBH 4
are A and B ?
19
----------------------------------------------------------------------------------------------------
Q.10 Acetylene is acidic but it does not react with (D) Cyclohexane is less dense than water
NaOH or KOH. Why ?
Q.7 Which of the following compounds will show
Q.11 CH  C – CH2 – CH = CH2, adds up HBr to give geometrical isomerism ? [IIT '98]
CH  C – CH2 – CHBr – CH3 while CH  C – CH = (A) 2-butene (B) Propene
CH2 adds up HBr to give CH2 = C. Br . CH = (C) 1-phenylpropene (D) 2-methyl-2-butene
CH2
Q.12 Chlorination of ethane to ethyl chloride is more Q.8 In the compound CH2 = CH – CH2 – CH2 – C 
practicable than the chlorination of n-pentane to CH, the C2 – C3 bond is of the type [IIT '99]
2 3 3
1-chloropentane. (A) sp – sp (B) sp – sp
3 2 3
(C) sp – sp (D) sp – sp
Q.13 Why n-pentane has higher boiling point than
neopentane? Q.9 Which one of the following alkenes will react
fastest with H2 under catalytic hydrogenation
condition
Colourless [IIT '2000]
O O3 R R R H
Q.14  W + Odourless
 
(A) (B)
gas
H H R H
IR
O O R R R R
H 2O 2 NaOH / CaO
  X  OH    Z (C) (D)
Y R H R R
O
Identify W, X, Y & Z. Q.10 Propyne and propene can be distinguished by
(A) conc. H2SO4 (B) Br2 in CCl 4
EXERCISE – IV(A) (C) dil. KMnO4 (D) AgNO3 in ammonia
Q.1 Alcoholic solution of KOH is a specific reagent
for
(A) Dehydration
.S [IIT '90] Q.11 In the presence of peroxide, hydrogen chloride
and hydrogen iodide do not give anti-
(B) Dehydrogenation Markovnikov addition to alkene because
(C) Dehydro halogenation [IIT '2001]
(D) Dehalogenation (A) both are highly ionic
(B) one is oxidising and the other is reducing
Q.2 Of the following, unsaturated hydrocarbons are (C) one of the step is endothermic in both the
[IIT '90] cases
(A) ethyne (B) cyclohexane (D) All the steps are exothermic in both cases
.J
(C) n-propane (D) ethene
Me Me
Q.3 1-chlorobutane on reaction with alcoholic potash H
gives [IIT '91] Q.12
(A) 1-butene (B) 1-butanol H
Me
(C) 2-butene (D) 2-butanol H
Hydrogenation of the above compound in the
N
Q.4 The hybridization of carbon atoms in C – C presence of poisoned paladium catalyst gives
single bond of HC  C – CH = CH2 is [IIT '91] [IIT '2001]
3 3 2 3
(A) sp – sp (B) sp – sp
2 2 2
(C) sp – sp (D) sp – sp (A) An optically active compound
Q.5 The product(s) obtained via oxymercuation (B) An optically inactive compound
(HgSO4 + H2SO4) of 1-butyne would be [IIT '97] (C) A racemic mixture
(A) CH3 – CH2 – C – CH3 (D) A diastereomeric mixture
O
Q.13 The reaction of propene with HOCl proceeds via
(B) CH3 – CH2 – CH2 – CHO
the addition of [IIT '2001]
(C) CH3 – CH2 – CHO + HCHO + +
(A) H in first step (B) Cl in first step
(D) CH3 – CH2 – COOH + HCOOH –
(C) OH in first step
+ –
(D) Cl and OH in single step
Q.6 When cyclohexane is poured on water, it floats,
because [IIT '97]
Q.14 The nodal plane in the -bond of ethene is
(A) Cyclohexane is in ‘boat’ form
located in [IIT '2002]
(B) Cyclohexane is in ‘chair’ form
(A) the molecular plane
(C) Cyclohexane is in ‘crown’ form
(B) a plane parallel to the molecular plane
20
----------------------------------------------------------------------------------------------------
(C) a plane perpendicular to the molecular plane Q.21 1-bromo-3-chlorocyclobutane when treated with
which contains the carbon-carbon -bond at right two equivalent of Na, in the presence of ether
angle which of the following will be formed ?
(D) a plane perpendicular to the molecular plane [IIT '2005]
which contains the carbon-carbon -bond. Br Cl
(A) (B) (C) (D)
Q.15 Consider the following reactions [IIT '2002]

H3C – CH – CH – CH3 + Br  ‘X’ + HBr Q.22 Cyclohexene is best prepared from cyclohexanol
D by which of the following : [IIT '2005]
CH3
(A) conc. H3PO4 (B) conc. HCl/ZnCl2
Identify the structure of the major product ‘X’
 (C) conc. HCl (D) conc. HBr
(A) H3C – CH – CH – CH2
D Q.23 CH3 – CH = CH2 + NOCl  P [IIT '2006]
CH3
 Identify the adduct.
(B) H3C – CH – C – CH3 (A) CH3 – CH – CH2 (B) CH3 – CH – CH2
D CH3 Cl NO NO Cl
 NO
(C) H3C – C – CH – CH3
(D) CH2 – CH2 – CH2
IR
(C) CH3 – CH2 – CH
D CH3
 Cl NO Cl
(D) H3C – CH– CH – CH3
CH3
CH2
Cl2 ,h
Q.24 H3C   N(isomeric products)
Q.16 Identify a reagent from the following list which CH3
can easily distinguish between 1-butyne and 2- fractional distillation
C5H11Cl        M(isomeric
butyne [IIT '2002]
(A) bromine, CCl4

.S
(B) H2, Lindlar catalyst
products)
What are N and M?
(A) 6, 6 (B) 6, 4
[IIT '2006]
(C) dilute H2SO4, HgSO4
(C) 4, 4 (D) 3, 3
(D) ammonical Cu2Cl 2 solution
HgSO
Q.25 The number of structural isomers for C6H14 is
Q.17 C6H5 – C  C – CH3  
4
 A [IIT '2003] [IIT '2007]
H2SO 4
(A) 3 (B) 4
O (C) 5 (D) 6
(A) (B)
.J
O
Q.26 The number of stereoisomers obtained by
(C) C6H5 – C = CHCH3 (D) C6H5 – CH = C – CH3
bromination of trans-2-butene is [IIT '2007]
OH OH (A) 1 (B) 2
OH (C) 3 (D) 4
H  x
Br2
Q.18 
  5 compounds
(mixture )
H 2 O Q.27 The synthesis of 3-octyne is achieved by adding
of molecular formula C4H8Br2 [IIT '2003] a bromoalkane into a mixture of sodium amide
N
Number of compounds in X will be : and an alkyne. The bromoalkane and alkyne

(A) 2 (B) 3 (C) 4 (D) 5 respectively are
[IIT-JEE 2010]
Q.19 2-hexyne can be converted into trans-2-hexene (A) BrCH2CH2CH2CH2CH3 and CH3CH2C  CH
by the action of : [IIT '2004] (B) BrCH2CH2CH3 and CH3CH2CH2C  CH
(C) BrCH2CH2CH2CH2CH3 and CH3C  CH
(A) H2 – Pd - BaSO4 (B) Li in liq. NH3
(C) H2 – PtO2 (D) NaBH4 (D) BrCH2CH2CH2CH3 and CH3CH2C  CH
Paragraph for question Nos. 28 and 29

Q.20 When Phenyl Magnesium Bromide reacts with An acyclic hydrocarbon P, having molecular
tert. butanol, which of the following is formed ? formula C6H10, gave acetone as the only organic
(A) Tert. butyl methyl ether [IIT '2005] product through the following sequence of
(B) Benzene reaction, in which Q is an intermediate organic
(C) Tert. butyl benzene compound.[IIT-JEE 2011]
(D) Phenol P (i) dil.H2SO4 /HgSOl4
 Q
 C 6H10  (ii)NaBH4 / ethanol
(iii) dil. acid
21
----------------------------------------------------------------------------------------------------
O Q.6 An organic compound E(C5H8) on hydrogenation
(i)conc. H2 SO 4
(catalytic amount ) gives compound F(C5H12). Compound E on
(  H 2O ) C ozonolysis gives formaldehyde and 2-

 (ii) O3
(iii) Zn/ H2 O H 3C CH3 ketopropanal. Deduce the structure of compound
Q.28 The structure of compound P is E. [IIT '1995]
(A) CH3CH2CH2CH2 – C  C – H
Q.7 Give the structures of the major organic products
(B) H3CH2C – C  CH2CH3 from 3-ethyl-2-pentene under each of the
H 3C following reaction conditions. [IIT '1996]
(a) HBr in the presence of peroxide
(C) H —C — C C — CH 3 (b) Br2 / H2O
H 3C (c) Hg(OAc)2 / H2O ; NaBH4
H3 C
(D) H3C —C — C C—H
H 3C Q.8 3, 3–Dimethyl–butan–2–ol loses a molecule of
water in the presence of concentrated sulphuric
Q.29 The structure of the compound Q is acid to give tetramethylethylene as a major
H 3C OH H3C OH product. Suggest a suitable mechanism.
IR
[IIT '1996]
H — C — C — CH2 CH3 H 3C — C — C — CH3
(A) (B) Q.9 Only mole of the compound A (molecular
H 3C H H 3C H formula C8H12), incapable of showing
H3 C OH
OH
stereoisomerism, reacts with only one mole of H2
on hydrogenation over Pd. A undergoes
H — C — CH2CHCH3
(C) (D)CH3CH2CH2 CH CH2CH3 ozonolysis to give a symmetrical diketone
H3C B(C8H12O2). What are the structure of A and B?
[IIT '1997]
Q.30
.S
The major product of the following reaction is
Q.10 Compound (A) C6H12 gives a positive test with
bromine in carbon tetrachloride. Reaction of (A)
RCH 2OH

H  ( anhydrous )
[IIT '2011] with alkaline KMnO4 yields only (B) which is the
O
potassium salt of an acid. Write structure
(A) a hemiacetal (B) an acetal formulae and IUPAC name of (A) and (B).
(C) an ether (D) an ester [IIT '1997]
Q.11 The central carbon–carbon bond in 1, 3–
butadiene is shorter than that of n-butane. Why ?
[IIT '1998]
.J
EXERCISE – IV(B)
Q.12 Discuss the hybridisation of carbon atoms in
allene (C3H4) and show the -orbital overlaps.
Cl
alc.KOH
[IIT '1999]
Q.1 (CH3)2C – CH2CH3   ? [IIT '1992]
Q.13 Complete the following [IIT '1999]
N
alc.KOH HBr
Q.2 C6H5CH2CHCH3   ?  ? 1
 2
 3

heat
Br
[IIT '1993] Q.14 Complete the following [IIT '1999]
D D HO CH3
Q.3 C(C6H12), an optically active hydrocarbon which C = C D C – C H
4 5 6
on catalytic hydrogenation gives an optically H
   D
H3C – C H3C – C
inactive compound, C6H14. [IIT '1993] H3C CH3 CH3 CH3
Q.4 Draw the stereochemical structure of the product Q.15 Carry out the following transformation in not
in the following reactions. [IIT '1994] more than three steps. [IIT '1999]
R–CC–R H
2
CH3 – CH2 – C  C – H 
Lindlar catalyst
O
Q.5 Write down the structures of the stereoismers CH3 – CH2 – CH2 – C – CH3
formed when cis-2-butene is reacted with
– –
bromine. [IIT '1995] Q.16 CH2 = CH is more basic than HC  C
[IIT '2000]
22
----------------------------------------------------------------------------------------------------
Q.17 On reaction with 4N alcoholic KOH at 175°C 1- (b) Bombykol also reacts with acetic anhydride to
pentyne is slowly converted into equilibrium give another ester, which on oxidative
mixture of 1.3% 1–pentyne (A), 95.2% 2-pentyne ozonolysis (O3/H2O2) gives a mixture of
(B) and 3.5% 1, 2-pentadiene (C). Give the butanoic acid, oxalic acid and 10-acetoxy
suitable mechanism of formation of A, B and C decanoic acid.
with all intermediates. [IIT '2001] Determine the number of double bonds in
Bombykol. Write the structures of compound A
Q.18 Identify X, Y and Z in the following synthetic and Bombykol. How many geometrical isomers
scheme and write their structures. Is the are possible for Bombykol ? [IIT '2002]
compound Z optically active ? Justify your
answer. [IIT '2002] Q.20 If after complete ozonolysis of one mole of
(A) CH3CH2C  C – H   ( i ) NaNH 2
 X monomer of natural polymer gives two moles of
( ii ) CH3 CH2Br CH3
H2 / PdBaSO4 alkaline KMnO4 CH2O and one mole of O = C – CH = O. Identify
    Y     Z
the monomer and draw the all-cis structure of
Q.19 A biologically active compound, Bombykol natural polymer. [IIT '2005]
(C16H30O) is obtained from a natural source. The
structure of the compound is determined by the
following reactions. [IIT '2002] OH 
IR
H , (i ) O3
Q.21   X   Y
(a) On hydrogenation, Bombykol gives a ( ii ) Zn / Cl3 COOH
compound A, C16H34O which reacts with [IIT '2005]
acetic anhydride to give an ester.
Identify X and Y.
.S
.J
N
23
----------------------------------------------------------------------------------------------------
ANSWER KEY
EXERCISE - I
Ques. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. B A B D A B B C A C B B A D B B A A D B
Ques. 21 22 23 24 25 26 27 28 29 30 31 32 33
Ans. B B B A C C C C D C A A C
EXERCISE – II
Ques. 1 2 3 4 5 6 7 8 9 10 11 12
Ans. A,C A,B,C,D A,B A,B,C,D A,B A,C A,C A,D D C D A
IR
Q.13 (A) 4 ; (B) 3; (C) 1 ; (D) 3,4 Q.14 C Q.15 (A) Q,R ; (B) P,R ; (C) Q,R ; (D) Q,R
Q.16 (A) B
EXERCISE – III
Q.1 (a) (A) =

.S , (B) =
H BH2 H HO
COO  COO 
H D D H
(b) DO H + H OD
COO  COO 
O
.J
CH3
CH2 – CH2 – C – H O = CH
Q.2 CH3 – C = CH2 Q.3 +
CH = O O = CH
C2H5 C2H5 CH2NO2
Q.4 A + B are two enatiomers H OH OH H Q.5 H CHO
OH H H OH H CHO
N
C2H5 C2H5 CH2NO2

C
Q.6 (i) C – C – C – C = C (ii) C – C – C = C – C – C(iii) C – C = C – C (iv) C – C = C – C – C = C
C C C
(v)
Q.7 (A) PhC  CMgx, (B) Ph – C  C – CH2Ar,

Ph H
(C) C = C (D) Ph – CH – Et
H CH2 – Ar Br
(E) Ph – CH = CH – Me trans, (F) Ph – CH – CH – Me (threo mix.),
OH OH
24
----------------------------------------------------------------------------------------------------
(G) Ph – COOH (H) Cold dil. KMNO4
Br
(I) HCO3H (J) CF3CH2CH2Br, (K)
Q.14
O O
O3
+ CO2 + H2O
OH
W O
H2O2
H
O O
O O
O O
IR
O (X) O
per acid
O O
O O
OH
Y O
.S
(Z)
EXERCISE – IV(A)
Ques. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. C A,D A C A D A,C D A D C B B A B D A B B B
Ques. 21 22 23 24 25 26 27 28 29 30
.J
Ans. D A A B C A D D B B
EXERCISE – IV(B)
Q.1 CH3 – C = CH – CH3
N
CH3
Br Br
CH2 – CH – CH3 CH = CH – CH3 CH – CH2 – CH3
alc.KOH HBr
Q.2   
heat
H
R R
CH3 – CH2 – C – CH = CH2
Q.3 Q.4 C = C
CH3 H H
(C6H12)
Me Me
CH2 CH2
H Br Br H
Q.5 + Q.6 (E) CH3 – C – CH
Br H H Br
Me Me
25
----------------------------------------------------------------------------------------------------
Br
Q.7 (a) (CH3 – CH2) CH – CH – CH3
OH
(b) (CH3 – CH2)2 C – CH – CH3
Br
(c) (C2H5)3C– OH
O
Q.9 (A) (B)
O
Q.10 (A) CH3 – CH2 – CH = CH – CH2 – CH3 (B) CH3CH2COOK
Q.13 1 ozonolysis ; 2  LiAlH4; 3  H2SO4 Q.14 (4)  HO – Cl ; (5)  CH3MgCl; (6)  H2O/H+
IR
Q.15 (1) NaNH2, (2) Me–I, (3) HgSO4 dilH2SO4 Q.16 Higher electronegativity of sp carbon
Et
Et Et
H OH
Q.18 (X)  Et – C  C – Et (Y)  C = C (Z)  H OH Z is meso so optically inactive
H H Et
Q.19
.S
Bombykol : HO – C – C – C – C – C – C – C – C – C – C = C – C = C – C – C – C
(A) HO (CH3)15CH3 4 geometrical isomers are possible

CH3 CH3 H
Q.20 (a) CH2 = C – CH = CH2 (b) C = C
(CH2 CH2)n
.J
O
Q.21 (X) , (Y) CH3 – C – (CH2)4 – CH = O
CH3
N
26
----------------------------------------------------------------------------------------------------

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IIT-JEE ChEmistry by N.J.

sir ORGANIC chemistry

Hydrocarbon (i) =CH2

CH3 H Pd–C is used for selectie reduction of

H2(1eq) CH3 H2/Ni

Electrolysis 2. Be2C + H2O  Be(OH)2 + CH4

(2) Dehydration of alcohol (E1) Ph

CH3 — C — CH2 

(4) Wittig Reaction Q.1 NaI  (A)

H Br 6. Diel’s Alder Reaction

8. OMDM (oxymercuration – demercuration) CH3 CH3

3. Gem dihalides Conversion of terminal to non – terminal alkyne

(1) Forward Reaction:–

(2) Reverse Reaction:–

Q. Identify major product:–

(4) CH3 — O C  C (1) CH  CH + 

(5) HgSO4 (A) NH2 NH2 / OH CH CH

ammonical Cu2Cl2 H— C C : Cu+ (red ppt.) 1.

Q.12 EXCEPTION OF CLEMMENSON:-

MECHANISM OF MOZINGO METHOD:-

Imp. Raney Nickel  H2 molecule is adsorbed on

(iii) (ii) Raney—Ni C—OEt O C—Ph

MECHANISM FOR OXYMERCURATION:

repeat the two

Q.1 Identify the product of the following

(xi)   HBO HBO

Q.2 What alkyl borane is formed from H H

(C) Solution of chlorine gas in water

CH3 CH3 Lindlar Na / NH3

CH3 Q.22 Mixture of one mole each of ethene and propyne

Q.16 A compound (C5H8) reacts with ammonical

(C) CH3OH , CH3 OH

Mg OH Q.2 Aqueous solution of potassium propanoate is

Q.4 Ph – C – CH3  Ph – CH2 – CH3

Q.13 List I List II

(C) (D) NBS

syn addition. Why ?

(A) bromine, CCl4

Number of compounds in X will be : and an alkyne. The bromoalkane and alkyne

Paragraph for question Nos. 28 and 29

Q.1 (a) (A) =

C2H5 C2H5 CH2NO2

Q.7 (A) PhC  CMgx, (B) Ph – C  C – CH2Ar,

(I) HCO3H (J) CF3CH2CH2Br, (K)

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