Hydrocarbons DPPs

CONTENT
S.No Pages
1. DPP-1 04 – 6
2. DPP-2 7–9
3. DPP-3 10 – 13
4. DPP-4 14 – 16
5. DPP-5 17 – 22
6. DPP-6 23 – 26
7. DPP-7 27 – 30
8. DPP-8 31 – 33
9. DPP-9 34 – 37
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Single Choice Question
Br
1. Na (A) Major product (A) is :

D.E
(A) (B) (C) (D)
Br
Na (A)
2.
D.E
Br
(A) (B) (C) (D)
Br
Na (A) se (B)
3.
D.E
Br
Product (B) will be :
Br
(A) (B) (C) (D)
CH 3 CH3
4. Na ?
Dry ether
Cl Cl
CH3 CH3 CH3
CH 3 CH3
(A) CH3 (B) (C) (D)
CH3
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Na
5. * Cl ?
Dry ether
Possible prodcuts are :(C = C14)
(A) * * (B)
* *
(C) * (D) All of these
+ –
6.
CH3COOK
+
Et COOK
Which of the gases evolved on the surface of anode.

(A) C2H6, H2 (B) C3H8, H2
(C) C2H6 + C4H6 + CO2 (D) C2H6 + C4H10 + CO2 
O
— +
ONa Electrolysis
7. — + major product will be
ONa
O
(A) 1-butyne (B) n-butane (C) 2-butene (D) 2-butyne
8. In kolbe’s electrolytic synthesis the pOH of solution will be
(A) decreases (B) Increases (C) Constant (D) None of these
9. Rate of decarboxylation of following carboxylic acid with sodalime will be in order

NaOH+CaO
CH3COOH
r1
NaOH+CaO
CH3CH2COOH r2
CH 3
|
NaOH+CaO
CH3 — CH — COOH
r3
(A) r1 > r2 > r3 (B) r3 > r2 > r1 (C) r2 > r3 > r1 (D) r1 > r3 > r2
10. Benzoic acid Product will be

NaOH + CaO
(A) (B) (C) (D)
NBS Na
11.    A  
Dry ether
 B 
What is the DBE (Double bond equivalent) value of product (B)?

(A) 3 (B) 4 (C) 5 (D) 6
12. Which Alkane can be prepared by wurtz's reaction in good yield.

(A) n-pentane (B) iso-pentane
(C) 2,3 -dimethyl butane (D) 2,2 -dimethyl butane
13. Which compound can react with Na metal.

(A) CH3–CH3 (B) CH2=CH2 (C) HCCH (D) CH3–O–CH3
14. An equimolar mixture of propanoic acid and KOH is electrolysed in the presence of water.
Which of the following products are not obtained?
(A) CH3–CH2–CH2–CH3 (B) CH2 = CH2
(C) CH3–CH2–CH3 (D) CH3 – CH3
15. Which of the following method is only usefull for the preparation of symmetrical alkanes?
(A) Corey House synthesis
(B) Wurtz reaction
(C) Catalytic hydrogenation of Alkene by H2/Ni/,
(D) All of these
Multiple Choice Questions

16. What are the products obtained on Kolbe's electrolysis of potassium salt of succinic acid and
potassium salt of fumaric acid, respectively
(A) Ethane (B) Ethylene (C) Acetylene (D) Benzene
Integer Type Questions
Br
Na
17. 
Dry ether
 Product(s)
14
(C14 : isotope of carbon)

Total number of different products obtained are :
18. Cu/ 
  Product
I
Find the number of resonating struicture possible of product :
D2
1. Product will be :
Pt
D H H H D D
(A) (B) (C) (D) B & C both
H D D D H H
O
H2
2. Ni
Me
Product of above reaction is
(A) Meso (B) racemic
(C) Diastereomer (D) Optically inactive mixture
H2
3. Ni
Me
product of above reaction is
(A) Meso (B) Racemic
(C) diastereomer (D) Optically active products.
D2
4. Pt

(A) Racemic (B) Diastereomer (C) Enantiomer (D) None
H2
5. Pt

(A) Racemic (B) Diastereomer (C) Enantiomer (D) Meso
6. Which of the following reagent not gives syn addition when react with alkyne.
(A) H2 + Pd (CaCO3 + Quinoline) (B) P — 2 catalyst
(C) Raney Nickel (D) Li/liq. NH3
CH3 H
7. CH3 — C  C — CH3  C=C
H CH3
Above conversion can be acheived by
(A) Na/ liq NH3 (B) Li / liqNH3 (C) Li / EtOH (D) All
8. Which of following will reacts with Na / liqNH3 ?
(A) (B) CH3 — C  C — CH3
(C) CH3 — C  C — H (D) All
O
9. CH3 — C  C — CH2 — CH = CH — CH2— C — Cl
(a) (b) (c)
Reactivity toward catalytic hydrogenation
(A) a > b > c (B) b > a > c (C) a > c > b (D) c > a > b
10. Reduction of the molecule shown below produces:
D /Ni
2
?
HO H
(A) A single enantiomer (B) A pair of enantiomer
(C) A pair of diastereomers (D) A racemic mixture
11. Compound X is chiral, and on hydrogenation yields a mixture of two stereoisomers, one of
which is chiral and the other achiral. Which of the following is compound X ?
CH3
CH3 CH 3
CH2 CH3 H
H H
CH2
(1) (2) (3)

(A) Compound X can only be (1) (B) Compound X can only be (3)
(C) Compound X can be (1) and (2) (D) Compound X can be (2) and (3)
12. Total number of alkene which on reduction give following alkane.
Ni/H
2
(X) 
Temperature

(A) 3 (B) 4 (C) 5 (D) 6
13. The reagent needed for converting
Ph H
Ph–CC–Ph  C C
H Ph
is :
(A) Catalytic Hydrogenation (B) H2/Lindlar catalyst
(C) Li/NH3 (D) Wilkinson catalyst
14. How many isomeric alkenes will give ispentane by catalytic hydrogenation?
(A) 2 (B) 3 (C) 4 (D) 5

15. Total number of structure alkene which on catalytic hydrogenation give 2,3-dimenthyl pentane.
16. X=Total number of Geometrical isomers possible for
Y = Total number of structural isomers possible for molecular formula C6H10Cl Br(containing
cyclohexane ring)

Z = Number of deuterium exchanged on prol onged treatment of OD/ D2O with
O
X  Y  Z
Find the value of  ?
 2 
17. (i) 3H2 /Pd

  (x) number of product including stereo isomers
(ii)
When two hydrogen of anthracene is replaced by bromine then number of meso isomer (y)
obtained is so, x +y = ?
18. Total number of alkene which on catalytic hydrogenation give 2,4-dimethyl pentane.
Cl2
1. n-Pentane (A) (no. of total product)
hv
(A) 2 (B) 3 (C) 4 (D) 5
Cl2
2. CH3—CH—CH2—CH2—CH3
| hv
CH3
Mono-chloro product (inculding steroisomers) are :
(A) 6 (B) 7 (C) 8 (D) 9
H
CH3 CH3
Br2,hv
3. Major Product
H H
H
CH3 CH3 Br
| | |
(A) CH3—CH—CH2Br (B) CH3—CBr—CH3 (C) CH3CH 2CH 2Br (D) CH3—CH—CH3
H H CH3
H H H H H H
4.
CH3 CH3 H H CH3 CH3
H H CH3
(I) (II) (III)

Correct order of mono bromination of given compound is :
(A) I > III > II (B) I > II > III (C) II > I > III (D) III > II > I
Cl
5. Cl2 ,hv fractional distillation
N(isomeric products) C4H6Cl2 
  M(isomeric products)
What are N and M ?

(A) 6, 6 (B) 6, 5 (C) 4,4 (D) 3, 3
6. Which alkane doesn't give optically active product on monochlorination in the presence of
light.
(A) (B) (C) (D)
7. A compound P gives two and only two monochlorination products, both achiral. The compound
P is:
(A) (B) (C) (D)
8. How many monochloro derivative are possible from photochlorination of isopentane. (including
stereoisomers)
(A) 4 (B) 5 (C) 6 (D) 7
9. Which alkane will give 2-possible products on monochlorination in the presence of light
(A) n-butane (B) Isobutane (C) Isopentane (D) Neopentane
10. Which of the following will give more than one different monochlorinated product ?
(A) (B) (C) (D)
11. Find number of monochlorinated product for the given compound (only structural) :
(A) 1 (B) 2 (C) 3 (D) 4
12. Find total number of monobrominated product for given compound (including stereoisomers) :
(A) 4 (B) 5 (C) 6 (D) 7
13. Find total number of enantiomer pair in product after monochlorination of following compound
:
(A) 0 (B) 1 (C) 2 (D) 3
More than one correct :

14. Photochemical fluorination is explosive while iodination is too slow to occur. The reaction for
this is :
(A) Bond dissociation energy of I2 is minimum
(B) Formation of CH3 – F is most exothermic
(C) Formation of H-F is most exothermic while formation of H-I is endothermic
(D) F2 has lower bond dissociation energy than Cl2 or Br2
Paragraph (15-16) :
Compounds which have different boiling points can be separated by fractional distillation
method. Enantiomers can't be separated by fractional distillation because they have same
physical properties like boiling point, melting point etc.
Diastereomers can be separated by fractional distillation because they have different physical
and chemical properties.
On the basis of above information answer the following given questions.
15. Find total number of dichlorinated product obtained by fractional distillation for following
reaction :
(A) 4 (B) 5 (C) 6 (D) 7
16. Find total number of monochlorinated product obtained by fractional distillation for following
compound on chlorination :
(A) 0 (B) 2 (C) 3 (D) 4
Comprehension (Q.17) :
At certain temperature, the % of monochlorinated products obtained for the following reactions
are given :
Cl2 /h
CH 3 – CH 2 – C H 2 – CH 3   CH 3 – CH 2 – C H 2 – CH 2 – Cl (28.30%) +
For all questions assume reactivity ratio to be same as in the above reactions.
The propagation step of monochlorination of alkane involves formation of the radical
intermediate.
 
R  H  Cl  R  H  Cl
The energy profile for the formation of free radical is described as :
for the compound (X)
17. For the compound (X), the following statement is true for the monochlorination via intermediate
(Q).
(A) 2-different products both optically active.
(B) 2-different products one active and other inactive.
(C) 2-different products and are distereomers of each other.
(D) Only one product is obtained.
Integer Type Question:

18. Total number of dichloroderivative of following compound (excluding stereoisomer)
19.
How many structural isomers of monobromocycloalkenes are obtained in this reaction (without
counting stereisomers) ?
Subjective Type Question :

20. Number of structural isomer obtain in mono halogenation of following compound & also give
total including stereoisomer :
(I) CH3 – CH3 (Ethane)
(II) (Propane)
(III) (Butane)
(IV) Isobutane
(V) (Pentane)
(VI) Isopentane
(VII) Neo pentane
(VIII) Methyl cyclo butane
(IX) Benzene
(X) 2-3-dimethyl butane
1. Find total dihalogenated product for following reaction (including stereoisomer) :
(A) 3 (B) 5 (C) 6 (D) 7
2. Number of monochlorinated product obtained on fractional distillation is :
(A) 6 (B) 8 (C) 9 (D) 11
3. Find total number of dihalogenated product for given compound (including stereisomerism) :
(A) 7 (B) 9 (C) 11 (D) 13
4. Find total number of dihalogenated optical active product for given reaction :
Cl2 ,h
3-chloropentane  
(A) 3 (B) 4 (C) 6 (D) 7
5. Which of the following gives total monochlorinated product odd in number after chlorination
(including stereoisomerism) ?
(A) (B) (C) (D)
X2
6. CH4   CH3 –X
X
Rate of reaction for different halogen :
(A) F2 > Cl2 > Br2 > I2 (B) Cl2 > F2 > Br2 > I2
(C) I2 > Br2 > F2 > Cl2 (D) F2 > Br2 > I2 > Cl2
Cl2 /h
7. CH3– CH3   CH3 – CH2 – Cl
Which of the following steps are not involved :


(A) CH3– CH3 + Cl  CH3 CH2 + HCl
 
(B) CH3 – CH3  CH3 CH2  H


(C) CH3 CH2 + Cl2  CH3 – CH2 – Cl + Cl
 
(D) Cl + Cl  Cl2
8. Which of the following is more reactive in halogenation :

(A) 1° hydrogen (B) 2° hydrogen (C) 3° hydrogen (D) vinylic hydrogen
9. Which has maximum b.p. and m.p. out of :
(A) I in both case (B) I, II (C) I, III (D) II, I
10. major product is :
(A) (B) (C) (D)
11. Which is the major product of the following reaction ?
(I) (II) (III) (IV)
(A) I (B) II (C) III (D) IV
12. Chlorination of CH4 involves the following steps :

    
(i) Cl2  2Cl (ii) CH4  Cl  CH3  HCl (iii) CH  Cl  CH Cl
3 3
Which of the following is rate determining ?
(A) Step (i) (B) Step (ii) (C) Step (ii) and (iii) both
13. Which of the following statement is correct in relation to the halogenation of alkane ?
(A) The reactivity of chlorine is less than bromine towards alkanes.

(B) For photochemical chlorination of methane, C l is formed in slowest step..
(C) Free radicals are pyramidal intermediate, stabilised by hyperconjugation and resonance.
(D) Bromine has much higher regioselectivity than chlorine in abstracting 3° hydrogen.
More than one correct :
Cl
14. 2

hv
(A) Number of enantiomers are 8

(B) Number of diastereomers are 4
(C) Number of enantiomers are 6
(D) Number of diastereomers are 8
15. Identify which of the following gives atleast one meso dichlorinated product :
(A) (B) (C) (D)
16.
Which statements is/are correct about photochemical chlorination of the above compound :
(A) The major product will be chiral carbon atom having optically active compound
(B) The intermediate free radical of the major proeduct is resonance stabilized
(C) The intermediate free radical is not formed
(D) The intermediate free radical is planer, and stablized by only hyperconjugation
Integer Type Question:

17. How many distinct monochlorinated products, (including stereoisomers) may be obtained
when the alkane shown below is heated in the presence of Cl2 ?
Match the column :

18. Column-I Column-II
Compound Total monochlorinated product
(including stereoisomerism)
(A) (P) Even
(B) (Q) Odd
(C) (R) 1
(D) (S) 6
HCl
1. Peroxide (X) (Major product)
Structure of (X) will be
Cl
Cl
Cl
(A) (B) (C) (D)
Cl
CH3
2. HBr Major product will be :
Peroxide
Br
CH3 CH3 CH3
(A) H (B) Br (C) (D)
Br H Br
3. Anti—Markownikoff’s addition of HBr is not observed in -

(A) Propene (B) But-2-ene (C) Butene (D) 1-Methylcyclohexene
4. Write mechanism best accounts for the transformation in the brackets ?

Cl
CH3
H—Cl Cl
?
+ +
(A)
+ +
(B)
+ +
+ 1,2-hydride
(C) shift
+ + +
(D)
5. Consider the following rearragement reaction:
Br
+
HBr + Br–
Which of the following reaction coordinates best represents the overall reaction ? (Note: the
units are arbitrary)
(A) (B) (C) (D)
6. The reaction of HBr with the following compound would produce :
OH
Br
OH OH
(A) (B)
Br
Br
Br Br
(C) (D)
Br
7. The product(s) of the following reaction can best be described as :
HBr
(A) A racemic mixture (B) A single enantiomer

(C) A pair of diasteromers (D) An achiral molecule
HCl
8. Me — CH — CH = CH — Ph W, W is
|
Et
(A) Me — CH — CH2 — CH — Ph (B) Me — CH — CH — CH2 — Ph

| | | |
Et Cl Et Cl
(C) Me — CH — CH — CH 2 (D) Cl — CH — CH — CH 2 — Ph
| | | | |
Cl Et Ph Et Me
CH3
CH2
HBr
9. CCl4
What is sterochemistry of products

(A) Optically inactive (B) Meso product
(C) Diastereomers (D) None of these
10. 1-Penten-4-yne reacts with 1 mol bromine at -80°C to produce :

(A) 4, 4, 5, 5-Tetrabromopentene (B) 1, 2-Dibromo-1, 4-pentadiene
(C) 1, 1, 2, 2, 4, 5-hexabromopentane (D) 4, 5-dibromopentyne
HBr/40°C
11.
Thermodynamically controlled product will be :
(A) (B)
Br Br
(C) (D)
Br Br
12. The reaction of CH3CH CH OH with HBr gives
(A) CH3 CHBrCH2 OH (B) CH3CH2CHBr OH
(C) CH3CHBrCH2 Br (D) CH3CH2CHBr Br
HBr/CCl4
(P)
Major
13. ; correct relationship between (P) and (Q) is
HBr/R2O2
hv (Q)
Major
(A) chain isomers (B) Positional isomers

(C) Geometrical isomers (D) Identical
HBr/CCl4
CH 2 (A)
Major
14.
HBr/R2O2
hv (B)
Major
Relationship between (A) and (B) is

(A) Chain isomers (B) Positional isomers
(C) Geometrical isomers (D) Functional isomers
15. Which alkene gives same product on reaction with HBr/CCl4 and HBr/ROOR separately?
(A) (B) (C) (D)
HBr
Product (1)
CCl 4
16. 1-Butene
HBr
Product (2)
Benzoyl
Peroxide
Relationship between product 1 and 2 is :

(A) Positional isomer (B) Functional group isomers
(C) Chain isomer (D) Metamer
HBr
17. 
CCl
A B
4
Product can show which type of isomerism

(A) Position (B) Geometrical (C) Optical (D) Identical
18. HBr 1 equivalent 
 major product is :
(A) Br (B)
Br
Br
(C) (D)
Br
HBr
Rate-1 (r 1)
19. (CCl4)
MeO
HBr
Rate-2 (r 2)
(CCl 4)
OMe
Find the correct answer :

(A) r1 > r1 (B) r1 < r2 (C) r1 = r2 (D) Can not compare
HBr
20.   major product is :
1 eq
CH3 Br
CH3
CH3
(A) (B) (C) (D)

Br
Br Br
21. Count the number of steps in given reaction
CH2 HBr
Br
(A) 2 (B) 3 (C) 4 (D) 5
HBr in CH 3 COOH
(A) Na/dry ether (B)
22.
HBr in R O O R
(C) Na/dry ether (D)
What is relationship between (B) and (D)

(A) Chain isomer (B) Position isomer (C) Homologous (D) Stereoisomers

HBr
23. 
CCl

4
Considering Kinetic & thermodynamic control product, which of the following can be formed?
(A) Racemic mixture (B) Diastereomer
(C) Positional isomer (D) Chain isomer.
H2
1. CH3 — C  C — CH3
Pd—BaSO4
Br2
(A) (B)
CCl4
(A) Meso (B) Racemic mixture (C) Diastereomers (D) All
2. CH3 — C  C — CH2 — CH = CH2

(a) (b)
Reactivity toward electrophilic addition reaction.
(A) a > b (B) b > a (C) a = b (D) Cannot predict
Br
3. 2

CCl
 P 
4
Which of the following statement best describes the above reaction?

(A) It is a stereospecific reaction.
(B) It is a stereoselective reaction.
(C) Type of reaction is electrophilic addition reaction
(D) All of the above are correct statements
22Br
4. 
CCl
 Total number of products obtained are :
4
(A) 2 (B) 3 (C) 4 (D) 5
Br
 2
 A 
5. CCl , 25ºC
4 , Thermodynamically control product.
major
Br Br
Br Br
Br Br
(A) (B) (C) (D)
Br Br
2 2 Cl /H O
6. H–CC–H 
 excess 
 Product is :
OH Cl Cl HO
Cl
CH CH CH CH
(A) (B) OHC CH (c) HOOC–CHCl2 (D)
Cl OH Cl HO Cl
H Br
7. CH3–CC–CH3 2
Pd BaSO4
  A  
2
CCl4
 B  ;
Na Br
CH3–CC–CH3 
liq. NH3
 (C) 
2
CCl4
 D 
Relation between (A) and (C), (B) and (D)
(A) Identical, Identical (B) Identical, Diastereomer
(C) Diastereomer, Identical (D) Diastereomer, Diastereomer
8. The major product of the following reaction is

CH3
Br
2

Dark
 ?
H3C
Br
H 3C CH3
Br CH3
(A) Br (B)
Br CH3
Br H3C CH3
H C
(C) Br 3 CH3 (D)
CH3 CH3
9. Product (B) is
H3C H2 /Pd/BaSO4
Br2
CH3   A 
CCl4
 B
CH3 CH3
H Br H Br
(A) H Br (B) H Br + its diastereomers
CH3 CH3
CH3 CH3
H Br H Br
(C) Br H + mirror image (D) Br H (single)
CH3 CH3
10. What is the relationship between the two product X and Y from the reaction written below
Br

2
CCl4
 X+Y
(A) Ehantiomers (B) Position isomers

(C) Diasteromers (D) Meso isomers
11. Which of the following reaction involves a radical mechanism ?
HBr NBS
(A) 
ROOR
(B) 
hv

Br Br
(C) CH4 
2
(D) 
2
H O

hv 2
Br
12. 
2
CCl4
 Identify product
(A) (B)
Br Br Br Br
Br
(C) (D)
Br
H  Br 1 eq Br2
13. 
CCl
 A(major) 
CCl4
 Product(s)
4
(A) A is
Br
(B) A is
Br
(C) Finally two isomeric products are obtained

(D) Plane polarized light rotates when passed through solution
Match the column

14. List-I List-II
[Relationship between(I) and (II)]
HBr/CCl4
(I)
Major
(P) (1) Identical

HBr/R2 O2
(II)
hv Major
Cl
(Q) 2

hv
(II) (2) Different compound
(I)
OH

OH C3H6O
(R) 
 II (3) Tautomers
(I)
HBr/CCl4
(I)
Major
(S) (4) Positional isomers

HBr/R2 O2
(II)
hv Major
Codes :
P Q R S
(A) 3 2 1 4
(B) 4 2 3 1
(C) 4 1 2 3
(D) 1 2 3 4
15.
What is the valuye of Y + Z
+
H3O
1.
Shape of intermediate produced during this reaction will be
(A) Square planer (B) tetrahedral (C) Trigonal planer (D) Pyramidical
2. Identify which compound is having odd number of H into D during prolonged treatmnet.
O OH O
O
(A) (B) (C) (D)
(i) BH 3/THF
- (A)
(ii) H 2 O2/OH Major
CH3 C CH
3.
HgSO4/
(B)
HgSO4
Major
Relationship between (A) and (B) is :

(A) Tautomers (B) Functional group isomers
(C) Positional isomers (D) Identical
4. Compound B is :
Br Br
CH=CH CH3
CH CH2
(A) C (B)
C
 
C Na CH
CH CH2
(C) C (D)
C
Me
HBr Hg(OAc)2
(A) (C)
CCl4 NaBH4
5. CH3CH2CH=CH 2 CH 3CH2C CH
HBr B2 H 6
(B)  (D)
R 2O 2 H 2O2/OH
Relation between A and B, C and D are :

(A) Position, chain (B) Position, Functional
(C) Chain, Identical (D) Metamer, Functional
CH3
6. What are the products obtained on hydroboration-oxidaiton of the given alkene
CH3 CH3 CH3 CH3
(I) (II) (III) (IV)

H OH H OH
OH H OH H
CH3 CH3
(V) (VI)
H HO
OH H
(A) I and III (B) II and IV (C) II and VI (D) III and V
7. What is the relation between the products formed ?

CH3
Hydroboration  oxidation
  Products
(A) Racemic mixture (B) Diastereomers

(C) Chain isomers (D) Position isomers
HgSO4/H2SO4
OH C CH (A)
8.
(1) Disiamyl Borane

(B)
(2) H 2O 2/NaOH
Relation between A & B is :

(A) Tautomer (B) Geometrical (C) Functional (D) Identical
9. When butyne is treated with aqueous H2SO4 in presence of HgSO4, the major product is
(A) Butanal (B) Butanone (C) Butenol (D) Buten-2-ol
10. Which of the following alkyne give aldehyde in kucherov reaction (Hg2+/H2SO4) ?
(A) HCCH (B) CH3–CCH (C) CH3–CC–CH3 (D) Ph–CCH
CH3
Hg OAc 
OH 
11. 2


NaBH4
P, Identify P ?
HO O
O O OH
(A) (B) (C) (D)
CH3 (i) Hg(OAC) ,H O

2 2
12. A.A is –
(ii ) NaBH4/NaOH/H 2O
OH
OH CH3
CH3 CH3
(A) (B) (C) (D)
OH
OH
Multiple Choice Question

13. Which of the following reactions gives 3-methyl butane-2-ol as the main product ?
1 BH3 / THF

(A) 2H SO /H O
4 2 (B)   
  2 H2O2 /OH
1 HgOAc 2 /H2O 1 HgOAc 2 /H2O

(C)    (D)   
2  NaBH4 /OH 2  NaBH4 /OH
BH3 / THF
14. (A) 
H O ,OH
 CH CH CH CHO
3 2 2
2 2
Hg OAc 2 ,H2O

(B) 
NaBH
 CH3COCH2CH3
4
(A) & (B) are isomers

O
PCl5 4NaNH 2CH  I
CH 3 C H  
2
  3
  CH3  C  C  CH3
C 
Na
(C) 
Liq. NH3
 (D)
H2
(D) 
Pd  BaSO
 (E)
4
Find the correct statement?

(A) A & B are position isomers
(B) D has lower BP than E
(C) A & C can be seperate by active metal Na
(D) Reaction of D with Br2/CCl4 is stereospecific
Matrix Type Questions

15. Match the reaction given in column I with intermediate & type of reaction in column II.
Column I Column II
(A) H2O (P) Carbocation

, 
NBS
(B) 
hv
 (Q) Free radical
,
Hydroboration
(C) 
Oxidation
 (R) Electrophilic addition reaction
H Br
(D) 
Peroxide
 (S) Rearrangement possible
,
(T) Multiple possible products
(including stereoisomer)
Integer Type Question
16.
Find the value of x
1. Suggest reagent and condition for the asymmetric synthesis of the epoxide given.
O
+ +
(A) H3O (B) H2O/HO (C) CH3CO3H (D) CH3CO 2H/H
CH3 H
18
(i) CH3COO OH
2. X. The probable structure of ‘X’ is
+
(ii) H3O
H CH 3
CH3 CH3 CH3 CH3

18 18 18
H OH H OH H OH H OH
(A) (B) (C) (D) 18
H OH OH H H OH H OH
CH3 CH3 CH3 CH3
3. In which of the following reaction formation of racemic mixture.

Br2 Cold, KMnO4
(A) CCl4
(B)
(C) (D) None of these
Na cold. KMnO 4
4. CH3 — C  C — CH3 (A) (B)
liq. NH3
(A) Meso (B) Racemic mixture (C) Diastereomers (D) All
H2
5. CH3 — C  C — CH3 (A)
Pd—BaSO4
cold. KMnO 4
(B). Compound (B) is :
(A) Meso (B) Recemic mixture (C)Diastereomers (D) All
6. Which of the following will decolourise alkaline KMnO4 solution ?
(A) C3H8 (B) CH4 (C) CCl4 (D) C2H4
7. Cold.KMnO4
A   Meso-butane-2,3-diol.
(A) is :
(A) Cis-2-butene (B) Trans-2-butene (C) 1-butene (D) Iso-butene
8.
(A) Position isomer (B) Diastereomers (C) Enantiomers (D) Identical
9. There are four alkenes with the molecular formula C8H18 that upon hydrogenation give 2,5 -
dimethylhexane. Out of those four alkenes, only one gives a meso product upon reaction
with osmium tetroxide. Draw the structure of that alkene.
(A) (B)
(C) (D)
10. What is the major product expected from the following reaction
cold alkaline

KMnO

4
(A) (B)
(C) (D)

11. Correct statement is
Br
(A) cis-2-butene 
2
CCl4
 meso
Br
(B) Trans-2butene 
2
CCl4
 meso racemic
Cold KMnO4
(C) cis-2-butene  meso
Cl
(D) 2

hv
3-monochloro product
Paragraph-1 (Q.12 to Q.13)
Compound A and B consist of 6 carbons each. The results of bromination (Br2/CCl4), and
dihydroxylation (addition of 2-OH groups) with KMnO4 are as follows :
Br2/CCl4
2 Products
A
KMnO 4
1 Products
Br2/CCl4
No Products
B
KMnO 4
No Products
12. Which of the following pairs given below could be A and B respectively.
(A) (B) ,
,
(C) (D) ,
,
13. The number of products formed by dehydroxylation with KMnO4 of 3,4-dimethyl cyclobutene
(consider all posible stereoisomers) are:
(A) 1 (B) 2 (C) 3 (D) 4
14. Cold KMnO4 (x) products


Cold KMnO4 (y) products.


Find the sum of x + y ?
1. CH3–CH=CH2 and CH3–CCH can be distinguished by
(A) conc. H2SO4 (B) Dil KMnO4
(C) Br2 in CCl4 (D) Ammoniacal AgNO3
2. O-xylene on ozonolysis will give

O O
CHO CH3—C = O
(A) | & CH3—C—CHO (B) | & CH3—C—CHO
CHO CH3—C = O
O
CH3—C = O CHO CH3—C = O CHO
(C) | & | (D) | , CH3—C—CHO & |
CH3—C = O CHO CH3—C = O CHO
3O3
3.
Zn+H2O
Products are
(A) CO2H (B) CO 2H (C) CHO (D) CH2OH
| | | |
CHO CO2H CHO CH2—CH 2—OH
CH3
CH3
4. How many different products are obtained on ozonolysis of o-xylene , m-xylene
CH3
CH3
and p-xylene
CH3
CH3
(A) 2,3,2 (B) 3,3,2 (C) 3,2,2 (D) 3,3,3
H2 /Ni Cl2/hv
C6H 14 (Q) Only 2 different
(P) (Mono chlorination)
monochlorinated
products are formed
C 6H12
5.
O3
(R)
Zn, H 2O
2 moles
After observing the above reaction sequence, identify reactant (T).
(A) (B)
(C) (D)
6. Which of the following is not a product of the following reaction
O ,Zn,H O
3
 2
Ozonolysis
 (Products)
O
CHO O
(A) (B) (C) (D) CH3–CHO
CHO CH 3 C CHO
7. A compound 'X ' on catalytic hydrogenation gives 1-methyl-3-isopropyl cyclohexane and on

ozonolysis gives HCHO and the following
CHO O
CH3
O
Which of the following is compound ‘X’ ?
(A) (B) (C) (D)
CH3
CH2 CH2 CH2
8. Identify which compound on oxidative ozonolysis give meso product
(A) (B) (C) (D)
9. In which of the following reaction position isomers will be formed?
(A) CH3–CH=CH2 (B) CH3–CH=CH2
O3
Zn
(C) (D) All of these
10. Find the structure for compound that can not be a reactant for following ozonolysis
O O
O
HO +
3
(X)   H H H
Zn/H O 2
H O
(A) (B) (C) (D)
11. Predict the structure of alkene which on ozonolysis give one acetaldehyde and other molecule
of Acetone ?
(A) (B) (C) (D)

 Hot KMnO
12. 2-Pentyne 
HgSO4 /H
 (A + B) 
4
 Major product(s)
(A) A & B are positional isomers
(B) Finally two product are formerd
(C) Finally four products are formed
(D) Products are chain isomer of each other
Mathc the Column
13. List-I List-II
Cl
(P) AlCl
3 (1) Products are geometrical isomers
O
 
(major)
CH2 Br
Na
(Q) 
dry ether
 (Product major) (2) A 8 member ring is formed as a
CH2 Br
proeduct.

COONa
(R) Electrolysis
  Product(s) (3) Double bond equivalent value of

COONa
product is 6
(S) O3 , Me2S Product (4) Reaction is an intramolecular wurtz

reaction
Codes :
P Q R S
(A) 3 2 1 4
(B) 3 4 1 2
(C) 2 1 4 3
(D) 1 2 3 4
Integer Type Question

1 O3
14. C10H20  X    (±) 2-methyl butanal
2  CH3 2 S
" cis alkene "
How many isomers of “X” are its distereomers ?
15. Identify in which reaction racemic-mixture formed
Br
2 NBS
(a) 
CCl
 (b)   (c) dil KMnO
4

4 
CH COOH
3 HBr
(d) 

 (e) HBr
  (f) 
R O

H3O 2 2
O 2 6 BH
 (i) CH3–CCH  
(g) 3
  (h) Ni /D2
Zn  H2O2 /HO

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CONTENT

1. Na (A) Major product (A) is :

(A) (B) (C) (D)

(A) (B) (C) (D)

(A) (B) (C) (D)

Possible prodcuts are :(C = C14)

(C) * (D) All of these

Which of the gases evolved on the surface of anode.

9. Rate of decarboxylation of following carboxylic acid with sodalime will be in order

10. Benzoic acid Product will be

(A) (B) (C) (D)

What is the DBE (Double bond equivalent) value of product (B)?

12. Which Alkane can be prepared by wurtz's reaction in good yield.

13. Which compound can react with Na metal.

Multiple Choice Questions

Integer Type Questions

(C14 : isotope of carbon)

Find the number of resonating struicture possible of product :

product of above reaction is

product of above reaction is

8. Which of following will reacts with Na / liqNH3 ?

(A) (B) CH3 — C  C — CH3

(C) CH3 — C  C — H (D) All

10. Reduction of the molecule shown below produces:

(1) (2) (3)

12. Total number of alkene which on reduction give following alkane.

(A) 3 (B) 4 (C) 5 (D) 6

13. The reagent needed for converting

Integer Type Questions

16. X=Total number of Geometrical isomers possible for

17. (i) 3H2 /Pd

(I) (II) (III)

What are N and M ?

(A) (B) (C) (D)

(A) (B) (C) (D)

(A) (B) (C) (D)

(A) 1 (B) 2 (C) 3 (D) 4

(A) 4 (B) 5 (C) 6 (D) 7

(A) 0 (B) 1 (C) 2 (D) 3

More than one correct :

(A) 4 (B) 5 (C) 6 (D) 7

(A) 0 (B) 2 (C) 3 (D) 4

for the compound (X)

Integer Type Question:

Subjective Type Question :

(VII) Neo pentane

(VIII) Methyl cyclo butane

(A) 3 (B) 5 (C) 6 (D) 7

2. Number of monochlorinated product obtained on fractional distillation is :

(A) 6 (B) 8 (C) 9 (D) 11

(A) 7 (B) 9 (C) 11 (D) 13

(A) (B) (C) (D)

8. Which of the following is more reactive in halogenation :

(A) I in both case (B) I, II (C) I, III (D) II, I

10. major product is :

(A) (B) (C) (D)

11. Which is the major product of the following reaction ?

(I) (II) (III) (IV)