Hydrocarbon-05- Assignments

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SECTION - I SUBJECTIVE QUESTIONS LEVEL - I 1. Acid catalysed dehydration of neopentyl alcohol (CH3)3CCH2OH yields 2 methyl 2 butene as the major product. Outline a mechanism showing all steps in its formation. 2. Identify the final products giving intermediates in each case : (a) F3C – CH = CH2 + HCl  (b) O2N – CH = CH2 + HCl  3. An organic compound (D) (C5H8) on hydrogenation gives compound (E) (C5H12). Compound (D) on ozonolysis gives formaldehyde and 2-keto-propanal. Deduce the structure of compound (D). 4. What are the products if addition of D2 to trans-2-pentene in presence of Ni- metal 5. Identify final products of H — C — CH3 H5C2 — C — H D2 ? (a) (I)OsO4, ether  (II) Na2SO3 / H2O (b) Now give the product(s) of the following giving mechanism : CH3 | D O / D CH3  C  CH  CH2 | CH3 2  6. How would you synthesize CH3CH2C CH from CH3CH2I. 7. Propene reacts with HBr to give isopropyl bormide but does not give n-propyl bromide. 8. How can you diffrencitate but-1-ene and But-2-ene? 9. Indicate allylic, vinyl, 1°, 2°, 3° hydrogens in the following compound. Give the sequence of reactivity for free radical substitution. CH3 CH CH CH2 CH2 CH CH3 CH3 10. Explain why the addition of HI to 3,3-dimethylbut-1-ene gives 2-iodo-2, 3-dimethylbutane as the major product and not the 1-iodo-3, 3-dimethyl-butane. 1. (a) An unknown alkene with the formula C7H12 undergoes oxidation by hot basic KMnO4 to yield after acidification only one product. C H (i) hot alk. KMnO4  H C COOH. Identify the alkene. 7 12 (ii) H3O 3 O (b) Starting with compounds C2H2 & C2H5Br outline a synthesis of meso 3, 4 dibromohexane. (c) How would you distinguish between but-1-yne and but-2-yne. 2. One mole of a hydrocarbon (A) reacts with one mole of bromine giving a dibromo compound C5H10Br2. Substance (A) on treatment with cold, dilute alkaline potassium permanganate solution forms a compound C5H12O2. On ozonolysis, (A) gives equimolar quantities of propanone and ethanal. Deduce the structural formula of (A). 3. Compound (A) (C5H8O2) liberated carbon dioxide on reacting with sodium bicarbonate. It exists in two forms neither of which is optically active. It yields compound (B) (C5H10O2) on hydrogenation. Compound (B) can be separated into enantiomorphs. Write the structure formulae for (A) and (B) giving reasons. 4. A compound (A) with molecular formula C5H10 reacts with dilute alkaline potassium permanganate to form compund (B) (C5H12O2). (A) on reduction yields 2-methylbutane and on ozonolysis forms acetone and acetaldehyde. Deduce the structural formula of (A) and (B). Write equation for the above reactions. 5. 448 ml of a hydrocarbon (A) having C, 87.80%; H, 12.19% has a mass of 1.64 g at STP. On hydrogenation it gives 2-methyl pentane. Treatment of (A) with acidic HgSO4 gives a new compound (B) (C6H12O). Compound (A) does not react with ammonical AgNO3. Find out the structure of (A)

Chemistry : Hydrocarbons
ASSIGNMENTS
SECTION - I
SUBJECTIVE QUESTIONS
LEVEL - I
1. Acid catalysed dehydration of neopentyl alcohol (CH3)3CCH2OH yields 2 methyl 2 butene as the
major product. Outline a mechanism showing all steps in its formation.
2. Identify the final products giving intermediates in each case :
(a) F3C – CH = CH2 + HCl 
(b) O2N – CH = CH2 + HCl 
3. An organic compound (D) (C5H8) on hydrogenation gives compound (E) (C5H12). Compound (D) on
ozonolysis gives formaldehyde and 2-keto-propanal. Deduce the structure of compound (D).
4. What are the products if addition of D2 to trans-2-pentene in presence of Ni- metal
H — C — CH3
H C
5 2 — C — H


2
D
?
5. Identify final products of
(a) 


4
2 3 2
, ether
(I) OsO
(II) Na SO /H O
(b) Now give the product(s) of the following giving mechanism :
2
3
3
|
D O /D
3 2
|
CH
CH C CH CH
CH

   

6. How would you synthesize CH3CH2C CH from CH3CH2I.
7. Propene reacts with HBr to give isopropyl bormide but does not give n-propyl bromide.
8. How can you diffrencitate but-1-ene and But-2-ene?
9. Indicate allylic, vinyl, 1°, 2°, 3° hydrogens in the following compound. Give the sequence of reactivity
for free radical substitution.
CH3 CH CH CH2 CH2 CH
CH3
CH3
10. Explain why the addition of HI to 3,3-dimethylbut-1-ene gives 2-iodo-2, 3-dimethylbutane as the major
product and not the 1-iodo-3, 3-dimethyl-butane.
LEVEL - II
1. (a) An unknown alkene with the formula C7H12 undergoes oxidation by hot basic KMnO4 to
yield after acidification only one product.
4
3
(i) hot alk. KMnO
7 12 (ii) H O
C H 

 C
H3 COOH
O
. Identify the alkene.
(b) Starting with compounds C2H2 & C2H5Br outline a synthesis of meso 3, 4 dibromohexane.
(c) How would you distinguish between but-1-yne and but-2-yne.
2. One mole of a hydrocarbon (A) reacts with one mole of bromine giving a dibromo compound C5H10Br2.
Substance(A) on treatment with cold, dilute alkalinepotassiumpermanganatesolution forms a compound
C5H12O2. On ozonolysis, (A) gives equimolar quantities of propanone and ethanal. Deduce thestructural
formula of (A).
3. Compound (A) (C5H8O2) liberated carbon dioxide on reacting with sodium bicarbonate. It exists in two
forms neither of which is optically active. It yields compound (B) (C5H10O2) on hydrogenation. Compound
(B) can be separated into enantiomorphs. Write the structure formulae for (A) and (B) giving reasons.
4. A compound (A) with molecular formula C5H10 reacts with dilute alkaline potassium permanganate to
form compund (B) (C5H12O2). (A) on reduction yields 2-methylbutane and on ozonolysis forms acetone
and acetaldehyde. Deduce the structural formula of (A) and (B). Write equation for the above reactions.
5. 448 ml of a hydrocarbon (A) having C, 87.80%; H, 12.19% has a mass of 1.64 g at STP. On hydrogenation
it gives 2-methyl pentane. Treatment of (A) with acidic HgSO4 gives a new compound (B) (C6H12O).
Compound (A) does not react with ammonical AgNO3. Find out the structure of (A) and explain the
reactions involved.
6. The hydrocarbon (A), adds one mole of hydrogen in the presence of a platinum catalyst to form
n-hexane. When (A) is oxidized vigorously with KMnO4, a single carboxylic acid, containing three
carbon atoms, is isolated. Give the structure of (A) and explain.
7. Shown below is the final step in a synthesis of the important perfume constituent, cis-Jasmone. Which
reagents would you choose to carry out this last step?
o
CH — C C – CH CH
2 2 3

o
(A)
cis - Jasmone
8. Deduce the structural formula of a compound, C10H10(A), that gives as the only organic compound,
2 2
HOOCCH CHCH COOH (B) on oxidative cleavage.
|
CH COOH
2
Chemistry : Hydrocarbons
9. Identify the products of 1, 2 and 1,4 addition reactions of
(a)   

2
1eq. Br
(b)  

1eq. HCl
10. 3 4
Li. NH dil. KMnO
420
n – BuC CMe A
 
 


2 3 2
2 H CO /H O
H
Lindlar's catalyst
B

 

C


Identify A, B and C with proper explanation.
LEVEL - III
1. cis-2-butene on treatment with Baye’s reagent gives meso diol whereas trans-2-butene on same
treatment results in formation of racemic mixture. Accounts for the difference.
2. 2-Butyne undergoes following reactions in steps indicated. Identify A to H.
2 2
2
H D / Pt
3 3 Ni B(P 2)
CH — C C — CH A B

 

 

2
D /Pt
Na /EtOH
C D

 

2 2
H Br
NiB(P 2)
E F


 
2 2
Br H
Ni
G H

 
3. Identify
(a) the chiral compound C, C10
H14
, that is oxidized with alk. KMnO4
to Ph COOH and
(b) the achiral compound D, C10
H4
inert to oxidation under the same condition.
4. Write the structures of (CH3
)3
N and (me3
Si)3
N. Are they isostructural? Justify your answers.
5. An organic compound E (C5
H8
) on hydrogenation gives compound F(C5
H12
). Compound (E) on
ozonolysis gives formaldehyde. Deduce the structures of compound (E).
6.
CH3
3
4
3 2
HCO H
KMnO ,
O , H O
X
Y
Z (mix)







. Identify X, Y, Z.
7. 3, 3-dimethyl-1-butene and HI react to give two products, C6
H13
I. On reaction with alc. KOH one
isomer, (I) gives back 3, 3-dimethyl-1-butene the other (J) give an alkene that is reducatively ozonised
to Me2
C=O. Give the structure of (I) and (J) and explain the formation of the latter.
8. (a) Give reason for the following :
When 1-pentene-r-yne is treated with HBr in equmolecular proposition, the addition takes place
on double bond and not on triple bond yielding thereby the product CH3
CH(Br)CH2
CCH.
(b) Prove a suitable mechanism for the following reaction
OH
CH3
CH3
Chemistry : Hydrocarbons
9. Complete the following reaction :
(i) CH2
1 2 3

 
 

(ii)
CH3
2
H
landlar catalyst

 major product
(iii) CH3
CH3
CH3
Br
2 5
C H OH


 major product.
10. Draw newman projection of relatively less stable staggered from of n-butane. The reason fo low
stability of this form is Vander Waal’s repulsion, torsional strain, or both.
SECTION - II
SINGLE CHOICE QUESTIONS
1. (CH3)3C—MgCl on reaction with D2O produces
(a) (CH3)3CD (b) (CH3)3OD
(c) (CD3)3CD (d) (CD3)3OD
2. Consider the following reaction:
•
3 3
3
CH – CH – CH – CH + Br X + HBr
| |
D CH

Identify the structure of major product X:
(a) CH
CH3
CH2
CH
D
C
H3 (b) C
CH3
CH3
CH
D
C
H3
(c) CH
CH3
CH3
C
D
C
H3 (d) CH
CH3
CH3
C
D
C
H3
3. The compound 1, 2-butadiene has
(a) only sp-hybridized carbon atoms
(b) only sp2-hybridized carbon atoms
(c) both sp- and sp2-hybridized carbon atoms
(d) sp-, sp2 and sp3-hybridized carbon atoms
4. The compound which reacts with HBr obeying Markownikoff’s rule is
(a) CH2 = CH2 (b)
CH
H
3 CH
H
3
C=C
(c)
CH
H
3 H
CH3
C=C (d)
H C
3
H C
3
H
H
C=C
5. Which one of the following alkenes will react faster with H2 under catalytic hydrogenation condition?
(a)
R
H
R
H
(b)
R
R
H
H
(c)
R
R
R
H
(d)
R
R
R
R
Chemistry : Hydrocarbons
6. The reaction of CH3CH = CH — —OH with HBr gives
(a) CH CHBrCH
3 2— —OH (b) CH CH CHBr
3 2 — —OH
(c) CH CHBr
3 —
CH2
—Br (d) CH CH CHBr
3 2 — —Br
7. The major product for the reaction,
CH3
CH = C – CH – CH – CH – CH
2 2 2 2
O


+
3
H O
will be
(a)
CH3
I
CH – C – CH – CH – CH – CH
3 2 2 2
O
I
OH
(b)
CH OH
2
CH3
OH
(c)
CH3
CH3
OH
(d)
CH OH
2
CH3
8. Which of the following is most stable conformation?
(a)
HO H
CH3
H OH
CH3
(b)
OH
OH
CH3
CH3
H
H
(c)
H OH
CH3
H OH
CH3
(d)
H CH3
OH
H
OH
CH3
9. The product obtained via oxymercuration (HgSO4 + H2SO4) of 1-butyne would be
(a) CH3
C
H3
O
(b) C
H3 O
(c) C
H3
O
+ CH2O (d) C
H3
O
OH
+ HCO2H
10. Point out (A) in the given reaction sequence:
2
3
Δ
O
H
/
O
CO
COOH
CH
2
)
B
(
)
A
( 2
3





 

(a) (b)
(c) (d)
11. CH3 –
3
CH
|
CH – CH = CH2 + HBr  A (predominant), A is
(a) CH3 – CH – CH – CH3
|
CH3
|
Br
(b) CH3 – CH – CH2 – CH2Br
|
CH3
(c) CH3 – C – CH2 – CH3
|
CH3
Br
|
(d) None is correct
12. Stability of CH3 – CH = CH – CH3 CH3 – C = C – CH3
|
CH3
(I) |
CH3
(II)
CH3 – C = CH2
(III)
|
CH3
CH3 – C = CH—CH3
|
CH3
(IV)
In the increasing order is
(a) I  III  IV  II (b) I  II  III  IV
(c) IV  III  II  I (d) II  III  IV = I
13.
H – C
||
H – C
A
4
KMnO
alkaline




 

|
CH3
CH3
|
Which is true about this reaction?
(a) A is meso 1, 2-butan-di-ol formed by syn addition
(b) A is meso 1, 2-butan-di-ol formed by anti addition
(c) A is a racemic mixture of d and l, 1, 2-butan-di-ol formed by anti-addition
(d) A is a racemic mixture of d and l, 1, 2-butan-di-ol formed by syn-addition.
Chemistry : Hydrocarbons
14. H – C
|| 
 
 2
Br
|
CH3
CH3
|
C – H
H
H
Br
Br
CH3
CH3
(A)
Which is true statement?
(a) A is formed by anti addition and is meso (b) A is formed by syn addition and is meso
(c) A is formed by anti addition and is racemic (d) A is formed by syn addition and is racemic
15. (A) cis-2-butene I
H
HCO3


 
 (B) trans-2-butene 


 

H
HCO3
II
Correct statements are
(a) I is racemic mixture by anti addition (b) II is meso compound by anti addition
(c) I is meso compound by syn addition (d) II is racemic compound by syn addition
16. B
OH
/
O
H
THF
/
BH
2
2
3



 
 CH2 
 


O
H3
A
A and B are
(a) CH2OH
both (b) CH3
both
OH
(c) CH3
OH
CH2OH, (d) CH3
OH
CH2OH,
,
17. 10 mL of a certain hydrocarbon requires 25 mL of oxygen for complete combustion and the volume of
CO2 product is 20 mL. What is the formula of hydrocarbon.
(a) C2H2 (b) C2H4
(c) CH4 (d) C2H6
18. The treatment of C2H5Mgl with water produces
(a) Methane (b) Ethane
(c) Ethanal (d) Ethanol
19. The order of reactivity of halogens towards halogenation of alkanes is
(a) F2 > Br2 > Cl2 (b) F2 > Cl2 > Br2
(c) Cl2 > F2 > Br2 (d) Cl2 > Br2 > F2
20. In presenceof peroxide, hydrogen chloride and hydrogen iodide do not give anti-Markownikoff’s addition
to alkenes because
(a) both are highly ionic
(b) one is oxidising and other is reducing
(c) one of the step is endothermic in both the cases
(d) all the steps are exothermic in both the cases.
SECTION - III
MULTIPLE CHOICE QUESTIONS
1. The product obtained in the reaction
2
Cl , hv
6 5 2 3 273 K
C H CH — CH 
is
(a) C6H5CHCl—CH3 (b) C6H5CH2CH2Cl
(c) C6H5CCl2—CH3 (d) C6H5CHClCH2Cl
2. Which of the following reactions will give an alkyne?
(a) Potassium fumarate electrolysis

 (b) CH3CBr2CHBr2
Zn /alcohol

(c) CH3CH2CHBr2
alc./KOH

 (d) CH3CHBrCH2Br 2
NaNH



3. Alkenes undergo
(a) substitution reactions (b) addition reactions
(c) ozonolysis (d) none of these
4. Which of the following statements are correct for geometrical isomers?
(a) The cis-isomer is more polar than the trans-isomer
(b) The boiling point of the cis-isomer is higher than that of the trans-isomer
(c) Geometrical isomers havedifferent physical poperties but their chemical properties, though similar,
are not identical.
(d) The stability of trans-isomers is greater than that of cis-isomers.
5. Which of the following contains acidic hydrogen?
(a) Ethene (b) Ethane
(c) Ethyne (d) Butyne-1
6. Which of the following reactions can be used to prepare methane?
(a) Clemmensen reduction
(b) Wurtz reaction
(c) Catalytic hydrogenation of methyl iodide
(d) Reduction of methyl iodide by using a zinc-copper couple
7. Methane is obained when
(a) sodium acetate is heated with soda lime (b) iodomethane is reduced
(c) aluminium carbide reacts with water (d) potassium acetate is electrolysed
8. Which of the following compounds cannot be prepared by the Wurtz reaction?
(a) CH3CH3 (b) 3 3
3
CH CH — CH
|
CH
(c) CH3CH2CH2CH2CH2CH3 (d) CH3CH2CH2CH3
Chemistry : Hydrocarbons
9. The nitration of propane with concentrated HNO3 gives
(a) CH3CH2CH2NO2 (b) 3 3
2
CH CHCH
|
NO
(c) CH3CH2NO2 (d) CH3NO2
10. Which of the following compounds exhibit geometrical isomerims?
(a) CH3CH=CH—COOH (b) Br—CH=CH—Br
(c) C6H5CH=NOH (d)
O
MISCELLANEOUS QUESTIONS
SECTION - IV
COMPREHENSION TYPE QUESTIONS
Write up - I
Freeradical substitution is main initiated by HELPR [Heat, Electricity, Light (U.V.), Peroxideor Radical].
The most common example of free radical substitution is the halogenation reaction Halogenation
reactions are mainly given by those hydrocarbons which have atleast one hydrogen on sp3 hybrid
carbon.
1. The major product obtained when isobutane is treated with chlorine in the presence of diffused sun
light is
(a) isobutylchloride (b) n-Butylchloride
(c) tert-Butylchloride (d) sec-Butylchloride
2. Analkaneby molecular weight 72 uponchlorination givesonemonochlorinationproduct. Thealkaneis
(a) 2-Methylbutane (b) n-Pentane
(c) 2, 2-Dimethylpropane (d) all the three above
3. The percentageof 1-bromo-2-methyl propane obtained in thephotochlorination of isobutaneis about
(a) 46% (b) 64%
(c) 56% (d) 1%
Write up - II
Alkenes undergo electrophilic addition reaction with Hg(OAc)2, BH3 and H2O. In all these cases
reaction is regioselective reaction. BH3 gives addition reaction via formation of four centred cyclic
transition state. Hg(OAc)2 gives addition reaction via formation of bridge carbocation as reaction
intermediate whereas water gives addition reaction via formation of classical carbocation.
4. In the given reaction
3
[X]
3 2 3 3
3 3 3
CH OH
| |
CH —C —CH CH CH —C —CH —CH
| | |
CH H C CH
 
[X] is :
(a) H2O/H2SO4
(b) Hg(OAc)2 followed by NaBH4
(c) BH3 followed by H2O2/NaOH
(d) all of these
Chemistry : Hydrocarbons
5. In the given reaction
2
2
(i) BD /THF
3 2 (ii) Br
3
CH —C CH [X]
|
CH
 

[X] is :
(a) 3 2
3
D
|
CH —C — CH — Br
|
CH
(b) 3 2
3
CH —CH —CH — Br
|
CH
(c) 3 2
3
Br
|
CH —C —CH D
|
CH
(d) 3 2
3
Br
|
CH —C — CH — Br
|
CH
6. The compound X in the following reaction
C CH
2 4 4
Dil. H SO /HgSO
X is


(a)
CH2CHO
(b)
COCH3
(c)
CH CH3
OH (d)
COCHO
MULTIPLE MATCHING TYPE QUESTIONS
Match the following
7. Match List-I with List_II and select the correct answer from the codes given below the lists :
List-I (Reaction) List-II (Product)
(P) CH3—CH2—CH=CH2
2
4
(i) Hg(OAc) / HOH
(ii) NaBH

 (A) 3 2 2
OH
|
CH — CH —CH —CH D
(Q) CH3—CH2—CH=CH2
2 3
4
(i) Hg(OAc) /CH OH
(ii) NaBH


 (B) 3 2 3
OH
|
CH — CH —CH —CH
(R) CH3—CH2—CH=CH2
2 3
4
(i) Hg(OAc) /CH COOH
(ii) NaBH

 (C)
3
3 2 3
OCOCH
|
CH — CH —CH — CH
(S) CH3—CH2—CH=CH2
2 2
4
(i) Hg(OAc) /H O
(ii) NaBD

 (D)
3
3 2 3
OCH
|
CH — CH —CH — CH
(P) (Q) (R) (S)
(a) B D C A
(b) D B C A
(c) B D A C
(d) B D C A
8. Column A Column B
(P)
2
Cl
light

 (A)
Cl
(Q)
CH3
2
Cl
light

 (B)
CH3
Cl
(R) 2
3
Cl
FeCl

 (C)
Cl
Cl
Cl
Cl
Cl
Cl
(S)
CH3
2
3
Cl
FeCl

 (D)
CH2Cl
(P) (Q) (R) (S)
(a) C D A B
(b) D C A B
(c) C D B A
(d) C A D B
Chemistry : Hydrocarbons
ASSERTION-REASON TYPE QUESTIONS
The question given below consist of an ASSERTION and the REASON. Use the following key for the
appropriate answers
(a) If both Assertion and Reason are correct and Reason is the correct explanation for Assertion
(b) If both Assertion and Reason are correct and Reason is not the correct explanation for
Assertion
(c) If Assertion is correct but Reason is not correct.
(d) If Assertion is incorrect but Reason is correct.
9. Assertion : 2-Butyne changes to trans-2-butene by Li/NH3.
Reason : 2-Butene has cis- and trans-isomers.
10. Assertion : Alkyl shift in a carbocation is a Lewis acids-base reaction.
Reason : Carbocation is an electrophile and can accept lone-pair from Lewis-base (alkyl).
.
SECTION - V
(PROBLEMS ASKED IN IIT-JEE)
A. Only one option is correct (Objective Questions)
1. The reagent(s) for the following conversion,
?


Br
Br H H
is/are
(a) alcoholic KOH (b) alcoholic KOH followed by NaNH2
(c) aqueous KOH followed by NaNH2
(d) Zn/CH3
OH
2. The number of structural isomers for C6
H14
is
(a) 3 (b) 4
(c) 5 (d) 6
3. Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound
E on further treatement with aqueous KOH yields compound F. Compound F is
(a) CHO (b) CHO
(c) COOH (d)
CO2H
CO2H
4. The number of stereoisomers obtained by bromination of trans-2-butene is
(a) 1 (b) 2
(c) 3 (d) 4
5. CH3—CH=CH2 + NOCl  P
Identify the adduct :
(a) 3 2
CH —CH —CH
|
|
NO
Cl
(b) 3 2
CH —CH —CH
|
|
NO Cl
(c) 3 2
NO
|
CH — CH — CH
|
Cl
(d) 2 2 2
CH — CH —CH
|
|
Cl
NO
Chemistry : Hydrocarbons
6. What would be the poduct formed when 1-bromo-3-chloro cyclobutane reacts with two equivalents of
metallic sodium in ether?
(a)
Br
(b)
Cl
(c) (d)
7. 2-phenyl propene on acidic hydration gives :
(a) 2-phenyl-2-propanol (b) 2-phenyl-1-propanol
(c) 3-phenyl-1-propanol (d) 1-phenyl-2-propanol
8. 2-hexyne gives trans-2-hexene on treatment with
(a) Li/NH3 (b) Pd/BaSO4
(c) LiAlH4 (d) Pt/H2
9. How many chiral compound are possible on mono chlorination of 2-methyl butane?
(a) 2 (b) 4
(c) 6 (d) 8
10. The nodal plane in the -bond of ethene is located in :
(a) the molecular plane
(b) a plane parallel to the molecular plane
(c) a plane perpendicular to the molecular plane which bisects the carbon-carbon -bond at right
angle
(d) a plane perpendicular to the molecular plane which contains the carbon-carbon -bond
B. More than one options are correct (Objective Questions)
1. Which one of the following has the smallest heat of hydrogenation per mole?
(a) 1-butene (b) trans-2-butene
(c) cis-2-butene (d) 1, 3-butadiene
2.
CH3
C
H3
CH3
2
Cl , hv
N
 (isomeric products) C5H11Cl fractional distillation
M

 (isomeric products).
What are N and M?
(a) 6, 6 (b) 6, 4
(c) 4, 4 (d) 3, 3
SUBJECTIVEQUESTIONS
1. An organic compound E (C5H8) on hydrogenation gives compound F(C5H12). Compound E on ozonolysis
gives formaldehyde and 2-ketopropanal. Deduce the structure of compound E. (1995)
2. Give the structure of the major organic products from 3-ethyl-2-pentene under each of the following
reaction conditions : (1996)
(a) HBr in the presence of peroxide
(b) Br2/H2O
(c) Hg(OAc)2/H2O, NaBH4
3. An alkyl halide, X, of formula C6H13Cl on treatment with potassium tertiary butoxide gives two isomeric
alkenes Y and Z (C6H12). Both alkenes on hydrogenation gives 2, 3-dimethyl butane. Predict the
structures of X, Y and Z. (1996)
4. Complete the following, giving the structures of the principal organic proudct : (1997)
Ph
Ph H
Br
2
KNO A
 

5. The hydrocarbon A, adds one mole of hydrogen in the presence of a platinum catalyst to form
n-hexane. WhenAis oxidized vigorously with KMnO4, a single carboxylic acid, containing three carbon
atoms, is isolated. Give the structure of A and explain. (1997)
6. Give reason for the following in one or two sentences : (1998)
“The central carbon-carbon bond in 1,3-butadiene is shorter than that of n-butane”.
7. Complete the following reaction with appropriate structures of products/reagents: (1998)
2 2
3
Br (i) NaNH (3.0 equivalent)
6 5 2 (ii) CH I
C H CH CH [A] [B]
  

8. Give reason for the following : (2000)
CH2=CH– is more basic than HCC–
9. What would be the major product in the following reaction? (2000)
CH3
2
H
Lindlar catalyst

10. Monomer A of a polymer on ozonolysis yields two moles of HCHO and one mole of CH3COCHO.
(a) Deduce the structures of A.
(b) Write the structure of “all cis”—form of polymer of compound A. (2005)
Chemistry : Hydrocarbons
ANSWERS
SECTION - I
(Subjective Questions)
Answers are given in the separate booklet (Level – I to Level – III)
SECTION - II
(Single Choice Questions)
1. (a) 2. (b)
3. (b) 4. (d)
5. (a) 6. (b)
7. (b) 8. (a)
9. (a) 10. (c)
11. (c) 12. (a)
13. (a) 14. (a)
15. (c, d) 16. (d)
17. (a) 18. (b)
19. (b) 20. (d)
SECTION - III
(Multiple Choice Questions)
1. (a, c) 2. (a, b, c, d)
3. (a, b, c) 4. (a, b, c, d)
5. (c, d) 6. (c, d)
7. (a, b, c) 8. (b)
9. (a, b, c, d) 10. (a, b, c)
SECTION - IV
(Comprehension Type Questions)
1. (c) 2. (c)
3. (d) 4. (a)
5. (a) 6. (b)
(Multiple Matching Type Questions)
8. (A) (R) (B) (S)
(C) (P) (D) (Q)
(Assertion Reason Type Questions)
9. (b) 10. (a)
SECTION - V
A. Only one option is correct (Objective Questions)
1. (b) 2. (c)
3. (a) 4. (a)
5. (a) 6. (d)
7. (a) 8. (a)
9. (b) 10. (a)
B. More than one options are correct (Objective Questions)
1. (b) 2. (b)
SUBJECTIVE
Answers are given in the separate booklet

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Hydrocarbon-05- Assignments

  • 1. Chemistry : Hydrocarbons ASSIGNMENTS SECTION - I SUBJECTIVE QUESTIONS LEVEL - I 1. Acid catalysed dehydration of neopentyl alcohol (CH3)3CCH2OH yields 2 methyl 2 butene as the major product. Outline a mechanism showing all steps in its formation. 2. Identify the final products giving intermediates in each case : (a) F3C – CH = CH2 + HCl  (b) O2N – CH = CH2 + HCl  3. An organic compound (D) (C5H8) on hydrogenation gives compound (E) (C5H12). Compound (D) on ozonolysis gives formaldehyde and 2-keto-propanal. Deduce the structure of compound (D). 4. What are the products if addition of D2 to trans-2-pentene in presence of Ni- metal H — C — CH3 H C 5 2 — C — H   2 D ? 5. Identify final products of (a)    4 2 3 2 , ether (I) OsO (II) Na SO /H O (b) Now give the product(s) of the following giving mechanism : 2 3 3 | D O /D 3 2 | CH CH C CH CH CH       6. How would you synthesize CH3CH2C CH from CH3CH2I. 7. Propene reacts with HBr to give isopropyl bormide but does not give n-propyl bromide. 8. How can you diffrencitate but-1-ene and But-2-ene? 9. Indicate allylic, vinyl, 1°, 2°, 3° hydrogens in the following compound. Give the sequence of reactivity for free radical substitution. CH3 CH CH CH2 CH2 CH CH3 CH3 10. Explain why the addition of HI to 3,3-dimethylbut-1-ene gives 2-iodo-2, 3-dimethylbutane as the major product and not the 1-iodo-3, 3-dimethyl-butane.
  • 2. LEVEL - II 1. (a) An unknown alkene with the formula C7H12 undergoes oxidation by hot basic KMnO4 to yield after acidification only one product. 4 3 (i) hot alk. KMnO 7 12 (ii) H O C H    C H3 COOH O . Identify the alkene. (b) Starting with compounds C2H2 & C2H5Br outline a synthesis of meso 3, 4 dibromohexane. (c) How would you distinguish between but-1-yne and but-2-yne. 2. One mole of a hydrocarbon (A) reacts with one mole of bromine giving a dibromo compound C5H10Br2. Substance(A) on treatment with cold, dilute alkalinepotassiumpermanganatesolution forms a compound C5H12O2. On ozonolysis, (A) gives equimolar quantities of propanone and ethanal. Deduce thestructural formula of (A). 3. Compound (A) (C5H8O2) liberated carbon dioxide on reacting with sodium bicarbonate. It exists in two forms neither of which is optically active. It yields compound (B) (C5H10O2) on hydrogenation. Compound (B) can be separated into enantiomorphs. Write the structure formulae for (A) and (B) giving reasons. 4. A compound (A) with molecular formula C5H10 reacts with dilute alkaline potassium permanganate to form compund (B) (C5H12O2). (A) on reduction yields 2-methylbutane and on ozonolysis forms acetone and acetaldehyde. Deduce the structural formula of (A) and (B). Write equation for the above reactions. 5. 448 ml of a hydrocarbon (A) having C, 87.80%; H, 12.19% has a mass of 1.64 g at STP. On hydrogenation it gives 2-methyl pentane. Treatment of (A) with acidic HgSO4 gives a new compound (B) (C6H12O). Compound (A) does not react with ammonical AgNO3. Find out the structure of (A) and explain the reactions involved. 6. The hydrocarbon (A), adds one mole of hydrogen in the presence of a platinum catalyst to form n-hexane. When (A) is oxidized vigorously with KMnO4, a single carboxylic acid, containing three carbon atoms, is isolated. Give the structure of (A) and explain. 7. Shown below is the final step in a synthesis of the important perfume constituent, cis-Jasmone. Which reagents would you choose to carry out this last step? o CH — C C – CH CH 2 2 3  o (A) cis - Jasmone 8. Deduce the structural formula of a compound, C10H10(A), that gives as the only organic compound, 2 2 HOOCCH CHCH COOH (B) on oxidative cleavage. | CH COOH 2
  • 3. Chemistry : Hydrocarbons 9. Identify the products of 1, 2 and 1,4 addition reactions of (a)     2 1eq. Br (b)    1eq. HCl 10. 3 4 Li. NH dil. KMnO 420 n – BuC CMe A       2 3 2 2 H CO /H O H Lindlar's catalyst B     C   Identify A, B and C with proper explanation.
  • 4. LEVEL - III 1. cis-2-butene on treatment with Baye’s reagent gives meso diol whereas trans-2-butene on same treatment results in formation of racemic mixture. Accounts for the difference. 2. 2-Butyne undergoes following reactions in steps indicated. Identify A to H. 2 2 2 H D / Pt 3 3 Ni B(P 2) CH — C C — CH A B        2 D /Pt Na /EtOH C D     2 2 H Br NiB(P 2) E F     2 2 Br H Ni G H    3. Identify (a) the chiral compound C, C10 H14 , that is oxidized with alk. KMnO4 to Ph COOH and (b) the achiral compound D, C10 H4 inert to oxidation under the same condition. 4. Write the structures of (CH3 )3 N and (me3 Si)3 N. Are they isostructural? Justify your answers. 5. An organic compound E (C5 H8 ) on hydrogenation gives compound F(C5 H12 ). Compound (E) on ozonolysis gives formaldehyde. Deduce the structures of compound (E). 6. CH3 3 4 3 2 HCO H KMnO , O , H O X Y Z (mix)        . Identify X, Y, Z. 7. 3, 3-dimethyl-1-butene and HI react to give two products, C6 H13 I. On reaction with alc. KOH one isomer, (I) gives back 3, 3-dimethyl-1-butene the other (J) give an alkene that is reducatively ozonised to Me2 C=O. Give the structure of (I) and (J) and explain the formation of the latter. 8. (a) Give reason for the following : When 1-pentene-r-yne is treated with HBr in equmolecular proposition, the addition takes place on double bond and not on triple bond yielding thereby the product CH3 CH(Br)CH2 CCH. (b) Prove a suitable mechanism for the following reaction OH CH3 CH3
  • 5. Chemistry : Hydrocarbons 9. Complete the following reaction : (i) CH2 1 2 3       (ii) CH3 2 H landlar catalyst   major product (iii) CH3 CH3 CH3 Br 2 5 C H OH    major product. 10. Draw newman projection of relatively less stable staggered from of n-butane. The reason fo low stability of this form is Vander Waal’s repulsion, torsional strain, or both.
  • 6. SECTION - II SINGLE CHOICE QUESTIONS 1. (CH3)3C—MgCl on reaction with D2O produces (a) (CH3)3CD (b) (CH3)3OD (c) (CD3)3CD (d) (CD3)3OD 2. Consider the following reaction: • 3 3 3 CH – CH – CH – CH + Br X + HBr | | D CH  Identify the structure of major product X: (a) CH CH3 CH2 CH D C H3 (b) C CH3 CH3 CH D C H3 (c) CH CH3 CH3 C D C H3 (d) CH CH3 CH3 C D C H3 3. The compound 1, 2-butadiene has (a) only sp-hybridized carbon atoms (b) only sp2-hybridized carbon atoms (c) both sp- and sp2-hybridized carbon atoms (d) sp-, sp2 and sp3-hybridized carbon atoms 4. The compound which reacts with HBr obeying Markownikoff’s rule is (a) CH2 = CH2 (b) CH H 3 CH H 3 C=C (c) CH H 3 H CH3 C=C (d) H C 3 H C 3 H H C=C 5. Which one of the following alkenes will react faster with H2 under catalytic hydrogenation condition? (a) R H R H (b) R R H H (c) R R R H (d) R R R R
  • 7. Chemistry : Hydrocarbons 6. The reaction of CH3CH = CH — —OH with HBr gives (a) CH CHBrCH 3 2— —OH (b) CH CH CHBr 3 2 — —OH (c) CH CHBr 3 — CH2 —Br (d) CH CH CHBr 3 2 — —Br 7. The major product for the reaction, CH3 CH = C – CH – CH – CH – CH 2 2 2 2 O   + 3 H O will be (a) CH3 I CH – C – CH – CH – CH – CH 3 2 2 2 O I OH (b) CH OH 2 CH3 OH (c) CH3 CH3 OH (d) CH OH 2 CH3 8. Which of the following is most stable conformation? (a) HO H CH3 H OH CH3 (b) OH OH CH3 CH3 H H (c) H OH CH3 H OH CH3 (d) H CH3 OH H OH CH3 9. The product obtained via oxymercuration (HgSO4 + H2SO4) of 1-butyne would be (a) CH3 C H3 O (b) C H3 O (c) C H3 O + CH2O (d) C H3 O OH + HCO2H
  • 8. 10. Point out (A) in the given reaction sequence: 2 3 Δ O H / O CO COOH CH 2 ) B ( ) A ( 2 3         (a) (b) (c) (d) 11. CH3 – 3 CH | CH – CH = CH2 + HBr  A (predominant), A is (a) CH3 – CH – CH – CH3 | CH3 | Br (b) CH3 – CH – CH2 – CH2Br | CH3 (c) CH3 – C – CH2 – CH3 | CH3 Br | (d) None is correct 12. Stability of CH3 – CH = CH – CH3 CH3 – C = C – CH3 | CH3 (I) | CH3 (II) CH3 – C = CH2 (III) | CH3 CH3 – C = CH—CH3 | CH3 (IV) In the increasing order is (a) I  III  IV  II (b) I  II  III  IV (c) IV  III  II  I (d) II  III  IV = I 13. H – C || H – C A 4 KMnO alkaline        | CH3 CH3 | Which is true about this reaction? (a) A is meso 1, 2-butan-di-ol formed by syn addition (b) A is meso 1, 2-butan-di-ol formed by anti addition (c) A is a racemic mixture of d and l, 1, 2-butan-di-ol formed by anti-addition (d) A is a racemic mixture of d and l, 1, 2-butan-di-ol formed by syn-addition.
  • 9. Chemistry : Hydrocarbons 14. H – C ||     2 Br | CH3 CH3 | C – H H H Br Br CH3 CH3 (A) Which is true statement? (a) A is formed by anti addition and is meso (b) A is formed by syn addition and is meso (c) A is formed by anti addition and is racemic (d) A is formed by syn addition and is racemic 15. (A) cis-2-butene I H HCO3      (B) trans-2-butene       H HCO3 II Correct statements are (a) I is racemic mixture by anti addition (b) II is meso compound by anti addition (c) I is meso compound by syn addition (d) II is racemic compound by syn addition 16. B OH / O H THF / BH 2 2 3       CH2      O H3 A A and B are (a) CH2OH both (b) CH3 both OH (c) CH3 OH CH2OH, (d) CH3 OH CH2OH, , 17. 10 mL of a certain hydrocarbon requires 25 mL of oxygen for complete combustion and the volume of CO2 product is 20 mL. What is the formula of hydrocarbon. (a) C2H2 (b) C2H4 (c) CH4 (d) C2H6 18. The treatment of C2H5Mgl with water produces (a) Methane (b) Ethane (c) Ethanal (d) Ethanol 19. The order of reactivity of halogens towards halogenation of alkanes is (a) F2 > Br2 > Cl2 (b) F2 > Cl2 > Br2 (c) Cl2 > F2 > Br2 (d) Cl2 > Br2 > F2 20. In presenceof peroxide, hydrogen chloride and hydrogen iodide do not give anti-Markownikoff’s addition to alkenes because (a) both are highly ionic (b) one is oxidising and other is reducing (c) one of the step is endothermic in both the cases (d) all the steps are exothermic in both the cases.
  • 10. SECTION - III MULTIPLE CHOICE QUESTIONS 1. The product obtained in the reaction 2 Cl , hv 6 5 2 3 273 K C H CH — CH  is (a) C6H5CHCl—CH3 (b) C6H5CH2CH2Cl (c) C6H5CCl2—CH3 (d) C6H5CHClCH2Cl 2. Which of the following reactions will give an alkyne? (a) Potassium fumarate electrolysis   (b) CH3CBr2CHBr2 Zn /alcohol  (c) CH3CH2CHBr2 alc./KOH   (d) CH3CHBrCH2Br 2 NaNH    3. Alkenes undergo (a) substitution reactions (b) addition reactions (c) ozonolysis (d) none of these 4. Which of the following statements are correct for geometrical isomers? (a) The cis-isomer is more polar than the trans-isomer (b) The boiling point of the cis-isomer is higher than that of the trans-isomer (c) Geometrical isomers havedifferent physical poperties but their chemical properties, though similar, are not identical. (d) The stability of trans-isomers is greater than that of cis-isomers. 5. Which of the following contains acidic hydrogen? (a) Ethene (b) Ethane (c) Ethyne (d) Butyne-1 6. Which of the following reactions can be used to prepare methane? (a) Clemmensen reduction (b) Wurtz reaction (c) Catalytic hydrogenation of methyl iodide (d) Reduction of methyl iodide by using a zinc-copper couple 7. Methane is obained when (a) sodium acetate is heated with soda lime (b) iodomethane is reduced (c) aluminium carbide reacts with water (d) potassium acetate is electrolysed 8. Which of the following compounds cannot be prepared by the Wurtz reaction? (a) CH3CH3 (b) 3 3 3 CH CH — CH | CH (c) CH3CH2CH2CH2CH2CH3 (d) CH3CH2CH2CH3
  • 11. Chemistry : Hydrocarbons 9. The nitration of propane with concentrated HNO3 gives (a) CH3CH2CH2NO2 (b) 3 3 2 CH CHCH | NO (c) CH3CH2NO2 (d) CH3NO2 10. Which of the following compounds exhibit geometrical isomerims? (a) CH3CH=CH—COOH (b) Br—CH=CH—Br (c) C6H5CH=NOH (d) O
  • 12. MISCELLANEOUS QUESTIONS SECTION - IV COMPREHENSION TYPE QUESTIONS Write up - I Freeradical substitution is main initiated by HELPR [Heat, Electricity, Light (U.V.), Peroxideor Radical]. The most common example of free radical substitution is the halogenation reaction Halogenation reactions are mainly given by those hydrocarbons which have atleast one hydrogen on sp3 hybrid carbon. 1. The major product obtained when isobutane is treated with chlorine in the presence of diffused sun light is (a) isobutylchloride (b) n-Butylchloride (c) tert-Butylchloride (d) sec-Butylchloride 2. Analkaneby molecular weight 72 uponchlorination givesonemonochlorinationproduct. Thealkaneis (a) 2-Methylbutane (b) n-Pentane (c) 2, 2-Dimethylpropane (d) all the three above 3. The percentageof 1-bromo-2-methyl propane obtained in thephotochlorination of isobutaneis about (a) 46% (b) 64% (c) 56% (d) 1% Write up - II Alkenes undergo electrophilic addition reaction with Hg(OAc)2, BH3 and H2O. In all these cases reaction is regioselective reaction. BH3 gives addition reaction via formation of four centred cyclic transition state. Hg(OAc)2 gives addition reaction via formation of bridge carbocation as reaction intermediate whereas water gives addition reaction via formation of classical carbocation. 4. In the given reaction 3 [X] 3 2 3 3 3 3 3 CH OH | | CH —C —CH CH CH —C —CH —CH | | | CH H C CH   [X] is : (a) H2O/H2SO4 (b) Hg(OAc)2 followed by NaBH4 (c) BH3 followed by H2O2/NaOH (d) all of these
  • 13. Chemistry : Hydrocarbons 5. In the given reaction 2 2 (i) BD /THF 3 2 (ii) Br 3 CH —C CH [X] | CH    [X] is : (a) 3 2 3 D | CH —C — CH — Br | CH (b) 3 2 3 CH —CH —CH — Br | CH (c) 3 2 3 Br | CH —C —CH D | CH (d) 3 2 3 Br | CH —C — CH — Br | CH 6. The compound X in the following reaction C CH 2 4 4 Dil. H SO /HgSO X is   (a) CH2CHO (b) COCH3 (c) CH CH3 OH (d) COCHO MULTIPLE MATCHING TYPE QUESTIONS Match the following 7. Match List-I with List_II and select the correct answer from the codes given below the lists : List-I (Reaction) List-II (Product) (P) CH3—CH2—CH=CH2 2 4 (i) Hg(OAc) / HOH (ii) NaBH   (A) 3 2 2 OH | CH — CH —CH —CH D (Q) CH3—CH2—CH=CH2 2 3 4 (i) Hg(OAc) /CH OH (ii) NaBH    (B) 3 2 3 OH | CH — CH —CH —CH (R) CH3—CH2—CH=CH2 2 3 4 (i) Hg(OAc) /CH COOH (ii) NaBH   (C) 3 3 2 3 OCOCH | CH — CH —CH — CH (S) CH3—CH2—CH=CH2 2 2 4 (i) Hg(OAc) /H O (ii) NaBD   (D) 3 3 2 3 OCH | CH — CH —CH — CH
  • 14. (P) (Q) (R) (S) (a) B D C A (b) D B C A (c) B D A C (d) B D C A 8. Column A Column B (P) 2 Cl light   (A) Cl (Q) CH3 2 Cl light   (B) CH3 Cl (R) 2 3 Cl FeCl   (C) Cl Cl Cl Cl Cl Cl (S) CH3 2 3 Cl FeCl   (D) CH2Cl (P) (Q) (R) (S) (a) C D A B (b) D C A B (c) C D B A (d) C A D B
  • 15. Chemistry : Hydrocarbons ASSERTION-REASON TYPE QUESTIONS The question given below consist of an ASSERTION and the REASON. Use the following key for the appropriate answers (a) If both Assertion and Reason are correct and Reason is the correct explanation for Assertion (b) If both Assertion and Reason are correct and Reason is not the correct explanation for Assertion (c) If Assertion is correct but Reason is not correct. (d) If Assertion is incorrect but Reason is correct. 9. Assertion : 2-Butyne changes to trans-2-butene by Li/NH3. Reason : 2-Butene has cis- and trans-isomers. 10. Assertion : Alkyl shift in a carbocation is a Lewis acids-base reaction. Reason : Carbocation is an electrophile and can accept lone-pair from Lewis-base (alkyl). .
  • 16. SECTION - V (PROBLEMS ASKED IN IIT-JEE) A. Only one option is correct (Objective Questions) 1. The reagent(s) for the following conversion, ?   Br Br H H is/are (a) alcoholic KOH (b) alcoholic KOH followed by NaNH2 (c) aqueous KOH followed by NaNH2 (d) Zn/CH3 OH 2. The number of structural isomers for C6 H14 is (a) 3 (b) 4 (c) 5 (d) 6 3. Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound E on further treatement with aqueous KOH yields compound F. Compound F is (a) CHO (b) CHO (c) COOH (d) CO2H CO2H 4. The number of stereoisomers obtained by bromination of trans-2-butene is (a) 1 (b) 2 (c) 3 (d) 4 5. CH3—CH=CH2 + NOCl  P Identify the adduct : (a) 3 2 CH —CH —CH | | NO Cl (b) 3 2 CH —CH —CH | | NO Cl (c) 3 2 NO | CH — CH — CH | Cl (d) 2 2 2 CH — CH —CH | | Cl NO
  • 17. Chemistry : Hydrocarbons 6. What would be the poduct formed when 1-bromo-3-chloro cyclobutane reacts with two equivalents of metallic sodium in ether? (a) Br (b) Cl (c) (d) 7. 2-phenyl propene on acidic hydration gives : (a) 2-phenyl-2-propanol (b) 2-phenyl-1-propanol (c) 3-phenyl-1-propanol (d) 1-phenyl-2-propanol 8. 2-hexyne gives trans-2-hexene on treatment with (a) Li/NH3 (b) Pd/BaSO4 (c) LiAlH4 (d) Pt/H2 9. How many chiral compound are possible on mono chlorination of 2-methyl butane? (a) 2 (b) 4 (c) 6 (d) 8 10. The nodal plane in the -bond of ethene is located in : (a) the molecular plane (b) a plane parallel to the molecular plane (c) a plane perpendicular to the molecular plane which bisects the carbon-carbon -bond at right angle (d) a plane perpendicular to the molecular plane which contains the carbon-carbon -bond B. More than one options are correct (Objective Questions) 1. Which one of the following has the smallest heat of hydrogenation per mole? (a) 1-butene (b) trans-2-butene (c) cis-2-butene (d) 1, 3-butadiene 2. CH3 C H3 CH3 2 Cl , hv N  (isomeric products) C5H11Cl fractional distillation M   (isomeric products). What are N and M? (a) 6, 6 (b) 6, 4 (c) 4, 4 (d) 3, 3
  • 18. SUBJECTIVEQUESTIONS 1. An organic compound E (C5H8) on hydrogenation gives compound F(C5H12). Compound E on ozonolysis gives formaldehyde and 2-ketopropanal. Deduce the structure of compound E. (1995) 2. Give the structure of the major organic products from 3-ethyl-2-pentene under each of the following reaction conditions : (1996) (a) HBr in the presence of peroxide (b) Br2/H2O (c) Hg(OAc)2/H2O, NaBH4 3. An alkyl halide, X, of formula C6H13Cl on treatment with potassium tertiary butoxide gives two isomeric alkenes Y and Z (C6H12). Both alkenes on hydrogenation gives 2, 3-dimethyl butane. Predict the structures of X, Y and Z. (1996) 4. Complete the following, giving the structures of the principal organic proudct : (1997) Ph Ph H Br 2 KNO A    5. The hydrocarbon A, adds one mole of hydrogen in the presence of a platinum catalyst to form n-hexane. WhenAis oxidized vigorously with KMnO4, a single carboxylic acid, containing three carbon atoms, is isolated. Give the structure of A and explain. (1997) 6. Give reason for the following in one or two sentences : (1998) “The central carbon-carbon bond in 1,3-butadiene is shorter than that of n-butane”. 7. Complete the following reaction with appropriate structures of products/reagents: (1998) 2 2 3 Br (i) NaNH (3.0 equivalent) 6 5 2 (ii) CH I C H CH CH [A] [B]     8. Give reason for the following : (2000) CH2=CH– is more basic than HCC– 9. What would be the major product in the following reaction? (2000) CH3 2 H Lindlar catalyst  10. Monomer A of a polymer on ozonolysis yields two moles of HCHO and one mole of CH3COCHO. (a) Deduce the structures of A. (b) Write the structure of “all cis”—form of polymer of compound A. (2005)
  • 19. Chemistry : Hydrocarbons ANSWERS SECTION - I (Subjective Questions) Answers are given in the separate booklet (Level – I to Level – III) SECTION - II (Single Choice Questions) 1. (a) 2. (b) 3. (b) 4. (d) 5. (a) 6. (b) 7. (b) 8. (a) 9. (a) 10. (c) 11. (c) 12. (a) 13. (a) 14. (a) 15. (c, d) 16. (d) 17. (a) 18. (b) 19. (b) 20. (d) SECTION - III (Multiple Choice Questions) 1. (a, c) 2. (a, b, c, d) 3. (a, b, c) 4. (a, b, c, d) 5. (c, d) 6. (c, d) 7. (a, b, c) 8. (b) 9. (a, b, c, d) 10. (a, b, c) SECTION - IV (Comprehension Type Questions) 1. (c) 2. (c) 3. (d) 4. (a) 5. (a) 6. (b)
  • 20. (Multiple Matching Type Questions) 8. (A) (R) (B) (S) (C) (P) (D) (Q) (Assertion Reason Type Questions) 9. (b) 10. (a) SECTION - V A. Only one option is correct (Objective Questions) 1. (b) 2. (c) 3. (a) 4. (a) 5. (a) 6. (d) 7. (a) 8. (a) 9. (b) 10. (a) B. More than one options are correct (Objective Questions) 1. (b) 2. (b) SUBJECTIVE Answers are given in the separate booklet