Hydrocarbon DPP

VIBRANT ACADEMY ORGANIC CHEMISTRY
Daily Practice Problems

(India) Private Limited Target IIT JEE 2022
CLASS : XII TIME : 45 MIN. DPP. NO.-28
(A) This DPP gives you an idea about mono and dihalogenated products of an reactant.
Compound Number of monochloroproduct Number of monochloroproduct
(excluding stereoisomer)
1.
2.
3.
4.
5.
6.
7.
8.
9. CH2
(B)
Compound Number of Dichloroproduct Optically active product
(including stereoisomer)
1. 1-chlorobutane
2. R-2-chlorobutane
3. 3-chloropentane
4. R-2-chloropentane
5. S-2-chlorobutane
6. R & S-2-chloropentane
7. R & S-2-chloro butane

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Q. How do you account for the formation of ethane during chlorination of methane?
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Q. Identify dihalogenation products (including stereo)
Cl
Cl2 / h
CH3
1.  
Cl2 / h
7. H Cl  
Cl CH2
Cl2 / h
2.   CH3
(R-form)
Cl2 / h
Br 8. Racemic mixture of  
2-chloro butane
Cl2 / h
3.  
Cl
Cl
Cl2 / h
Cl2 / h 9.  
4.  
Cl Cl
Cl2 / h
5.   CH3
Cl2 / h
10.  
CH3
Cl2 / h
6. Cl H   Cl
Cl2 / h
CH2 11.  
CH3
12. How are the following conversions carried out :
CH3
(i)
........................................................................................................................................................
........................................................................................................................................................
(ii) CH3 – CH = CH2 CH3 – CH – CH3
CH3 – CH – CH3
........................................................................................................................................................
........................................................................................................................................................
(iii) CH3 – CH = CH – CH3  CH3 – CHO
........................................................................................................................................................
........................................................................................................................................................
Q. Identify product including stereo chemistry
H3O H3O
A A
Ni/D2 Ni/D2
B B
CH3 CH3 Cold dil. KMnO4 7. CH3 – CH = CH2
1. Cold dil. KMnO4
C C
Br2, CCl4 Br2, CCl4
D D
H3O H3O
A A
Ni/D2 Ni/D2
CH3 B B
2. Cold dil. KMnO4 8. CH3 – C  C – CH3 Cold dil. KMnO4
C C
CH3 Br2, CCl4 Br2, CCl4
D D
H3O H3O
A A
Ni/D2 Ni/D2
B B
CH3 CH2CH3
3. Cold dil. KMnO4 Cold dil. KMnO4
C 9.
C
Br2, CCl4 Br2, CCl4
D D

H3O
A
H3O
Ni/D2 A
CH3
B Ni/D2
4. Cold dil. KMnO4 B
C 10. Cold dil. KMnO4
CH2CH3
Br2, CCl4 C
D Br2, CCl4
D
H3O
A
Cold dil. KMnO4
Ni/D2 COOH A
B 11. Br2, CCl4
5. Cold dil. KMnO4 B
C COOH
Br2, CCl4
D
Cold dil. KMnO4

A
H3O 12. Br2, CCl4
A
B
Ni/D2
CH3 B
6. Cold dil. KMnO4
C
CH3 Br2, CCl4
D
13. CH2 = CH – CH2 – C  CH
CH3 Br2, CCl4
Cold dil. KMnO4 A
A Cold KMnO4
Br2, CCl4 16. H Cl B
B D2, Ni
1 mole C
CH
CH3 Cold dil. KMnO4 CH2
A
14. H Br Br2, CCl4
B O
CH 17. 
2 H
(cis) Ni
CH
CH3 No. of stereoisomers and relation b/w products
CH3
Cold dil. KMnO4
A
15. H Br Br2, CCl4
B
CH
(trans)
CH
CH3
Q. Identify product including stereo chemistry.
CH3
H O
C
1. 3
C
8. ( X)
2. Ph – CH = CH – CH3 H O
3 products
H
C
H3O
3.   C
H3C H
H3C Ph
9. C
CH2
H3O  C
4.   A + B H3C Ph
Ph CH3
10.
H3C Ph
OH
5.
C  C – CH3 11. Cold dil. KMnO 4

   
6. ( X)
CH3 products
C=C
H H
C  C – CH3
7. H ( Y) 12. ( X)
products products
C=C
H CH3
H CH2
21.
13. ( Y) Write mechanism ?

products
14. (X) isomer of C4H8 (alkene only) ( Y)

products
Q. Number of stereoisomers and relationship be-

Br2 , CCl4 tween product.
15.   
O
||
H2
22. 

Pd – C
Br2 , CCl4
16.   
O
||
H2
23. 

Pd – C
Br2 , CCl4
17.   
24. CH 2 Cl 2
+ Br2  
25. CH 2 Cl 2
+ Cl2  
CH2
Br2 , CCl4 ||
18.   
26. CH2 Cl2
+ Cl2  
27. CH 2 Cl 2
+ Br2 
19. cold dil. KMnO 4 ( Y) 
    
products
( i) OsO 4
28.  
(ii ) H2O
20. CH3
29. HBr

SCQ :
Cold . KMnO 4
1. A     Meso-butane-2,3-diol.
(A) is :
(A) Cis-2-butene (B) Trans-2-butene (C) 1-butene (D) Iso-butene
2. 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 ?
(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)
2Br2
3. Total number of products obtained are :
CCl4
(A) 2 (B) 3 (C) 4 (D) 5
Br2
(A)
4. CCl4, , Thermodynamically control product.
major
25ºC
Br Br Br Br
Br Br
(A) (B) (C) (D)
Br Br
HBr
5. CCl4 A+B
Product can show which type of Isomerism

(A) Position (B) Geometrical (C) Optical (D) Identical
6. HBr(1 equivalent) Major product is :
Br
(A) Br (B) (C) (D)
Br
Br
Br2/CCl4
Meso 2,3-dibromobutane (X)
7. (A)
Cold KMnO4
(Y)
Product (Y) is :
(A) Racemic mixture (B) Meso (C) Diastereomers (D) Constitutional isomers
Cl2
8. Number of possible dichlorinated optically active isomer will be ?
h
(A) 2 (B) 4 (C) 7 (D) 9
Cl2
9. Mono-chloro products
h
A mixture of all isomers possible from the mono-chlorination of the structure is subjected to fractional distillation,
then how many fractions will be obtained ?
(A) 2 (B) 3 (C) 4 (D) 5
3Cl2/hv
10. C6H6Cl6
Addition
reaction Product(x)
Find the number of meso & optically active isomers possible for product(x) respectively
(A) 2,7 (B) 3,6 (C) 8,2 (D) 7,2
Comprehension (Q.11 to Q.12) :

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 :
11. Which of the following pairs given below could be A and B respectively :
(A) (B)
(C) (D)
12. The number of products formed by dihydroxylation with KMnO 4 of 3,4-dimethyl cyclobutene
(consider all posible stereoisomers) are :
(A) 1 (B) 2 (C) 3 (D) 4
MCQ :
HBr
13. CCl4
Considering Kinetic & thermodynamic control product, which of the following can be formed ?
(A) Racemic mixture (B) Diastereomer
(C) Positional isomer (D) Chain isomer.
Br2
14. CCl4 Identify product
Br Br
(A) (B) (C) (D)
Br Br Br Br Br Br
15. Correct statement(s) about the compound (x) and product is (are):-
H2
Ni Product(s)?
CH3 CH3
(X)
(A) ‘X’ has 1 optically active diastereomer (B) Two products are obtained
(C) Single optically active product is formed (D) Diastereomeric mixture is obtained
H-Br(1 eq) Br2

16. A(Major) Product(s)
CCl4 CCl4
(A) A is
Br
(B) A is
Br
(C) Finally two isomeric products are obtained.
(D) Plane polarized light rotates when passed through solution of product.
Subjective :
3H2/Pd
17. (i) (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. Consider all possible isomeric carbonyl compounds (including stereoisomers) of MW = 86. All these isomers
are independently reacted with Ni/H2. (Note : Stereoisomers are also reacted separately)
The total number of carbonyl compounds that give only racemic product(s) is/are.
19. Identify in which reaction racemic-mixture formed

Br2 NBS
(a) CCl4 (b)

dil KMnO4 CH3COOH

(c) (d) 
H3O
HBr HBr
(e) (f) R2O2
O3 Ni/D2
(g) (h)
Zn
B2H6
(i) CH3–CCH
H2O2/HO
20. Total number of structure alkene which on catalytic hydrogenation give 2, 3-dimenthyl pentane.
H2 Hot KMnO4
21. B A diethyl ketone + CO2 ()
Ni (Alkene)
Cl2, hv
fractional
X Y fractions
Distillation
(number of isomeric
monohaloginated
products)
Identify magnitude of X-Y.
OXYMERCURATION-DEMERCURATION (OMDM)
OMDM is a hydration process of alkene according to Markovnikoff’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 is complete, sodium borohydride and hydroxide ion are added to the
reaction mixture.
( i ) Hg( OAc ) ,H O,THF
R–CH = CH2       
2 2
R  CH  CH 3
( ii ) NaBH 4 ,HO ¯
|
OH
AcO¯ = CH3COO¯
Mechanism for oxymercuration:

OAc
OAc +
Hg
H2O
CH3CH = CH2 + Hg — OAc CH3CH — CH2 CH3CHCH2—Hg—OAc
+
OH
+ AcO¯
H
¯OAc
CH3CHCH2—Hg—OAc
OH + AcOH
Sodium borohydride (NaBH4) converts the carbon-mercury bond into a carbon-hydrogen bond. Because the
reaction results in the loss of mercury, it is called demercuration.
NaBH
4 
CH3CHCH2 — Hg—OAc   CH3CHCH3 + Hg + AcO¯
HO ¯
| |
OH OH
1. Identify the product of the following reaction.
CH3
( i) Hg( OCOCH )  CH OH
     3 
3 2

(i) (
i ) Hg ( CF3COO ) 2 ,CH 3OH
  (ii) ( ii ) NaBH4 ,OH
( ii ) NaBH 4 , HO ¯
(i ) Hg( OAc )2 ,H2O (i ) Hg( OAc )2 ,H2O

(iii)      (iv)     
(ii ) NaBH4 ,OH (ii ) NaBH4 ,OH
CCH
OH (i ) Hg( OAc )2 ,H2O (i ) Hg( OAc )2 ,H2O
         
(v) (ii ) NaBH4 ,OH
(vi) (ii ) NaBH4 ,OH
2. How could each of the following compounds be synthesized from an alkene by OMDM?
OH OCH2CH3 CH 3 CH 3
| |
(i) (ii) (iii) CH 3CCH 2 CH 3 (iv) CH 3CCH 2 CH 3
| |
OH OCH 3
3. What is the total number of stereoisomers that can exist for the given molecule ?
OH
Cl
(A) 3 (B) 4 (C) 6 (D) 8
4. The compound hexa-1, 5-diene was subjected to oxymercuration and a mixture of diols of formula C6H12O2
was formed
1. Hg(OAc) 2 / H2O
mixture of diols
2. NaBH4 C6H14O2
hexa-1, 5-diene
How many stereoisomers would you expect there to be?
(A) 1 (B) 2 (C) 3 (D) 4
+2
Hg
5. CH3 – C  C – CH3 (A) (B)
H2SO4
Structure of (A) & (B) respectively :-
OH O O OH
(A) , (B) ,
OH O OH
(C) , (D) , CH3CHO
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¯ ,H2 O2 , H2 O
Hydroboration oxidation
CH3CH2CH2OH
(i ) BH THF CH3 COOH
CH3CH = CH2  3   (CH3CH2CH2)3 B Hydroboration reduction
CH 3CH 2CH 3
AgNO3
Dimerisation
CH 3CH 2CH 2
CH 3CH 2CH 2
Mechanism of Hydroboration:
H H
+ 2
CH3CH=CH2  CH3—C—C—H  CH 3CH 2 CH 2 (CH3CH2CH2)3 B
|
H—BH2 BH 2
H BH2
— an alkylborane
More stable
transition state
Mechanism of oxidation :
HOOH + HO¯  HOO¯ + H2O
1. Identify the product of the following reaction.
BH ,THF
( i ) BH ( i ) BH 3 

(i) CH2 = CH2  3  (ii)  3  (iii) H2O / OH
(ii ) HO ¯,H 2O 2 , H 2O (ii ) HO ¯,H 2O 2 , H 2O
BH ,THF BD3, THF

3 

(iv) H2O / OH
(v) CH3COOH
BH3, THF
CH3COOD
BT3, THF
CH3COOD
CCH
(i ) BH ,THF
 3 i  BH3 i  BH3
(vi) (vii)   (viii)  
(ii ) H2O2 / HO  ii H2O2 , HOO– ii H2O2 , HOO–
i  BH3
(ix)   (x)
ii H2O2 , HOO–
(i) BH (i) BH
   3    3
(xi) ii H2O2, HOO– (xii) R – CC–R ii H2O2, HOO–
(i) BH (i) BH
(xiii) CH3 – C  CH    3 (xiv)    3
ii H2O2, HOO– ii H2O2, HOO–
(i) BH3
(xv)       
ii H2O2, HOO–
2. What alkyl borane is formed from hydroboration of each alkene ?
(A) (B) (C) (D)
3. Draw the products formed when each alkene is treated with BH3 followed by H2O2, HO O– include the
sterochemistry at all stereogenic centres.
(A) (B) (C) H3C (D)
4. What alkene can be used to prepare each alcohol as the exclusive product of a two step hydroboration–
oxidation sequence?
(A) (B) (C)
Mix problems on OMDM, HBO & Ozonolysis.
(i) Hg (OAc)2, H2O

(A)
(ii) NaBH4
1.
(i) BH3, THF
(B)
(ii) H2O2
(i) Hg (OAc)2, MeOH No. of products

–
(A) (Including stereo)
O
(ii) NaBH4,OH
2.
(i) BH3, THF No. of products
(B) (Including stereo)
(ii) H2O2
(i) BD3 . THF

(A)
(ii) H2O2
3.
(i) Hg (OAc)2 MeOH
–
(B)
O
(ii) NaBD4, OH
4. Choose the major product of the following reaction
H
1. BH3
–
2. H2O2 / HO
H H H H
(A) (B) (C) (D)
OH H H OH
OH OH OH
5. How many of the following compounds gives same products on HBO (Hydroboration oxidation) and OMDM
(oxymercuration-demercuration).
—CC—
(i) CH3 – C  C – CH3 (ii) HC CH (iii) Ph – C  C – Ph (iv)
(v) (vi) (vii) (viii)
6. From the following data, propose the correct structure for terpinoline, a natural product found in many plants
H2 1. O3 O O
terpinoline + ||
Pd / C 2. Me2S
O
O
(A) (B) (C) (D)
7. An unknown compound was treated with ozone followed by (CH3)2S and the following product was obtained.
O O
|| ||
O O
H H
Which of the following compounds might have been the unknown?
(i) (ii) (iii) (iv)
(A) i (B) ii (C) i or iii (D) ii or iv

8. Predict the major products (A) and (B).
CH3 (A)
DM
OM
H O
3
(B)
(OMDM is Oxymercuration-Demercuration)
CH3 OH CH3 OH CH3
*
(A) A = + ; B= OH (±)
CH3 CH3 OH CH3 OH

*
(B) A = OH (±) ; B = +
CH3
OH
(C) A = B =
(±)
CH3 OH CH3 OH
(D) A = B = +
9. Choose the major product of the following reaction.
1. BH3 : THF
–
2. H2O2 / OH
H H H H OH H OH
OH OH OH
H H H
(A) (B) (C) (D)
+ + + +
enantiomer enantiomer enantiomer enantiomer
10. Relation between (P) & (Q), (R) & (S) is
(P) (R)
O O
HB HB
Ph – C  CH ; Ph – CH = CH2
OM OM
DM DM
(Q) (S)
HBO : Hydroboration oxidation. OMDM : Oxymercuration demercuration.

(A) (P) and (Q) are Positional isomers (B) (P) & (Q) are Functional group isomers
(C) (R) and (S) are Positional isomers (D) (R) & (S) are Functional group isomers
Comprehension (Q.11 to Q.13)

Compound A is a chiral alkene of formula C6H12. The stereochemistry of A is R. It undergoes hydroboration to
give a chiral alcohol B of formula C6H14O. Oxymercuration of A gives a pair of alcohols. C1 and C2, that are
chiral and stereoisomers of each other. Sulfuric acid catalyzed addition of water to A gives a third alcohol D
of the same formula, but it is achiral. Finally palladium catalyzed hydrogenation of A gives an achiral alkane
of formula C6H14.
C6H14 achiral alkane
H2 / Pd
H2SO4 / H2O (A) 1. BH3

C6H14O achiral alcohol C6H14O chiral alcohol
2. H2O2 ; NaOH (B)
(D)
1. Hg(OAc)2 / H2O
2. NaBH4
C6H14O chiral alcohols

stereoisomers of each other
(C1 and C2)
11. Compound (A) is
H CH3 H CH3 H CH3 H Et

(A) (B) (C) (D)
12. Compound (B) is

H CH3 H CH3
H CH3 H CH3
(A) (B) (C) (D)
OH HO OH OH
13. Relationship between C1 and C2 is :
(A) Enantiomer (B) Diastereomer (C) Constitutional isomer (D) None of these
OZONOLYSIS : The reaction of alkene or Alkyne with ozone (O3) followed by hydrolysis is known as ozonolysis.
It is of two types : (I) Reductive ozonolysis  In presence of reducing agent
(II) Oxidative ozonolysis  In presence of oxidising agent
Reducing agents : Zn, H2O or Zn, CH3COOH or (CH3)2S or (Ph)3P etc.
Oxidising agents : H2O2 or R  C  O  O  H or Ag2O etc.
||
O
R R’ R O 
R’ H O/Zn R
O3 3
C=C C C Reductive C=O + R’–C–H
step I
R H –70°C R H ozonolysis R
O O O
Oxidative [SCT- Cut the double bond

Example 1 : ozonolysis H2O2 and paste two oxygen atoms
and vice versa]
R–C–R + R’–C–OH
O O
Mechanism :
R
– R
R R O R C O R’
O –
C  C O + C=O
+ O O R 
C R’ C O H
R’ H O
H
R
R
O – R—C—O
C O
R  O
R’ R–C–R + R’–C–H
O
O=C C
H R’ O O
H
Note : In case of oxidative ozonolysis aldehyde (not ketone) further undergoes oxidation which gives
acid as product.
(i) O3
Example 2: R—CC—R’ R—C—C—R’ Product is vic
(ii) Zn, H2O
dicarbonyl compound
Reductive O O
ozonolysis
(i) O3 (ii) CH3 C–O–O–H
O
Per acid
R—C—OH R’—C—OH (Products are carboxylic acid)
+
O O
1. Give the product of the following reaction.
(i) H2C = CH2 (

i ) O3
 (ii) CH3–CH = CH2 (
i ) O3

( ii ) Zn / H 2O ( ii ) Zn / H 2O
CH 3
|
(iii) (
i ) O3
 (iv) CH 3  C  CH 2 (
i ) O3

( ii ) Zn / H 2O ( ii ) Zn / H 2O
(v) (
i ) O3
 (vi) (
i ) O3

( ii ) Zn / H 2O ( ii ) Zn / H 2O
H
(i) O O3
(vii) H2C=CH–CH2–CH=CH–CH3 3
 (viii)  ?
( ii ) Zn / H 2O Zn / H 2O
(ix) O
3/

Zn / H 2O
2. Find out the structure of reactant.
O
(i) X ( i ) O3
 O + HCHO (ii) X (
i ) O3
 O
( ii ) Zn / H 2O ( ii ) Zn / H 2O
C10 H12
O
O
CH3 H
(iii) X (
i ) O3
 + C=O + C=O
( ii ) Zn / H 2O
H3C H
O
O
(iv) X (
i ) O3
 + O (v) C6 H 4 ( i ) O3
 C3H2O3
( ii ) Zn / H 2O (X) ( ii ) Zn / H 2O
H H
O O
(i) O
(vi) X 3  + HCHO
C12 H18 (ii ) Zn / H 2O
O
O
(i) O
O
(vii) X 3  + O=C=O + O + HCHO
( ii ) Zn / H 2O
C12 H18
H
O
(viii) X ( i ) O3
O+ (ix) X ( i ) O3
 CH 3  CH 2  C  H
( ii ) Zn / H 2O ( ii ) Zn / H 2O ||
O
O
H
(x) X (
i ) O3
 O + O (xi) X (
i ) O3

( ii ) Zn / H 2O H ( ii ) Zn / H 2O
O
3. How many ozonoid structures (including stereoisomers) are possible in given reaction.
3 O 3 O 3 O
(a) CH2 = CH2 Zn

/ H2O
(b) CH3 – CH = CH – CH3 Zn

/ H2O
(c) CH3 – CH = CH2 Zn

/ H2O
Suggest a appropriate path to achieve product B.
4.
........................................................................................................................................................
5. HC  CH 
........................................................................................................................................................
6.
........................................................................................................................................................
7. Ozonolysis of compound A gives one product, 2-butanone. Palladium-catalyzed hydrogenation of A gives

compound B (C8H18), which is a meso product.
Give the structures of A and B.
O
1. O3 H2
A B
2. Me2S Pd-C
C8H18
meso
H H
(A) A = (B) B = (C) A = (D) B =
8. Choose the alkene(s) that would give the two products of the following ozonolysis reaction.
O O
1. O3 || ||
alkene H +
2. Me2S H || || H H
O O
(1) (2) (3) (4)
(A) 1 (B) 2 (C) 2 or 3 (D) 3 or 4
9. Choose the correct product of the following reaction.
1. O3
2. Zn / HOAc
O O
O O O || O
(A) (B) H H (C) (D)

H O O
10. How many products (count only those containing one or more carbonyls) will be formed in the following
reaction?
O3
?
(CH3)2S
(A) 0 (B) 1 (C) 2 (D) 3
11. Find product(s) (A) and (B)

(A)
O3
Zn
O3
H2O2
(B)
(A) A = O + O (B) A = O + CH3COOH
(C) B = O + CH3COOH (D) B = O + O

12. Structure of Limonese can be :
O
O3 Zn O
Limonese HCHO +
C10H16 AcOH
(A) (B) (C) (D)
13. Find the major product(s) (A) and (B) ?

O
Cl
(A)
AlCl3
Cl
(B)
AlCl3
O
(A) A = (B) B = (C) A = (D) B =
CLASS : XII(ALL) TIME : 45 MIN. DPP. NO.-36
Q. IDENTIFY THE PRODUCT
CH3
Hot alk . KMnO 4

1.    (A)
Hot alk . KMnO 4
7.    (F)
H3C
CH3
Hot alk. KMnO 4

2.    (B)
Hot alk. KMnO 4

8.      (G)
CH3
H3C
Hot alk. KMnO 4
3.  (C)
    
Hot alk . KMnO 4

9.    (H)
H3C CH3
CH3
Hot alk . KMnO 4
4.  (D)
    
H3C
CH3
CH3 Hot alk. KMnO 4

H3C CH3 10.    (I)
Hot alk . KMnO 4

5.    (E) H3C
Hot alk . KMnO 4

11.    (J)
CH3
Hot alk . KMnO 4

6.    (F) Hot alk . KMnO 4
12.    (K)
H3C CH3 Hot alk . KMnO 4
13.    (L) CH3
H3C Hot alk. KMnO
4  (M)
14. CH3     

Hot alk. KMnO 4
24.      (W)
15. H3C CH3 Hot alk. KMnO 4

   (N) H3C
H3C CH3
Hot alk . KMnO 4 Hot alk. KMnO 4

16.    (O) 25.    (X)
CH3
Hot alk . KMnO 4

H3C 26.    (Y)
CH3 Hot alk . KMnO 4
17.    (P)
CH3 Hot alk . KMnO 4

27. H3C    (Z)
CH3
CH3
H3C Hot alk. KMnO
18. 4  (Q)
CH3     

H3C
Hot alk . KMnO 4

19. H3C CH2       (R)
Hot alk . KMnO 4

20.    (S)
Hot alk. KMnO 4

21.    (T)
CH3
Hot alk. KMnO 4
22.    (U)
CH3
CH3
Hot alk. KMnO 4
23.    (V)
CLASS : XII(ALL) TIME : 45 MIN. DPP. NO.-37
Q. IDENTIFY THE PRODUCT
O
CH3
Hot alk. KMnO 4
   (A) CH3
1. 9. Hot alk. KMnO 4
   (I)
H3C
CH3
Hot alk . KMnO 4
10. H3C    (J)
Hot alk. KMnO 4
2.     
 (B)
O
CH3
Hot alk . KMnO 4
3.     
 (C) 11. Hot alk . KMnO 4
   (K)
CH3
Hot alk. KMnO 4 CH3

4.    (D) Hot alk . KMnO 4
12.    (L)
O
CH3
O CH3
Hot alk. KMnO 4
5. H3C CH3     
 (E)
H3C CH3 Hot alk . KMnO 4 Hot alk . KMnO 4

6.    (F) 13.    (M)
O
Hot alk . KMnO 4

7.    (G) O CH3
Hot alk . KMnO 4

8.    (H)

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VIBRANT ACADEMY ORGANIC CHEMISTRY

Daily Practice Problems

7. R & S-2-chloro butane

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C  C – CH3 11. Cold dil. KMnO 4

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13. ( Y) Write mechanism ?

14. (X) isomer of C4H8 (alkene only) ( Y)

Q. Number of stereoisomers and relationship be-

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(A) 2 (B) 3 (C) 4 (D) 5

Product can show which type of Isomerism

Comprehension (Q.11 to Q.12) :

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H-Br(1 eq) Br2

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19. Identify in which reaction racemic-mixture formed

dil KMnO4 CH3COOH

Identify magnitude of X-Y.

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Mechanism for oxymercuration:

(i ) Hg( OAc )2 ,H2O (i ) Hg( OAc )2 ,H2O

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BH ,THF BD3, THF

2. What alkyl borane is formed from hydroboration of each alkene ?

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

(A) (B) (C) H3C (D)

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(A) (B) (C)

Mix problems on OMDM, HBO & Ozonolysis.

(i) Hg (OAc)2, H2O

(i) Hg (OAc)2, MeOH No. of products

(i) BD3 . THF

4. Choose the major product of the following reaction

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

(v) (vi) (vii) (viii)

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

(i) (ii) (iii) (iv)

(A) i (B) ii (C) i or iii (D) ii or iv

CH3 CH3 OH CH3 OH

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10. Relation between (P) & (Q), (R) & (S) is

HBO : Hydroboration oxidation. OMDM : Oxymercuration demercuration.

Comprehension (Q.11 to Q.13)

C6H14 achiral alkane

H2SO4 / H2O (A) 1. BH3

C6H14O chiral alcohols

11. Compound (A) is

H CH3 H CH3 H CH3 H Et

12. Compound (B) is

Oxidative [SCT- Cut the double bond

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(i) H2C = CH2 (

2. Find out the structure of reactant.

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Suggest a appropriate path to achieve product B.

7. Ozonolysis of compound A gives one product, 2-butanone. Palladium-catalyzed hydrogenation of A gives

(1) (2) (3) (4)