TOPIC WISE REVIEW PART TEST-II

TEST - III-HC
SINGLE CORRECT CHOICE TYPE (+3, -1)
Q.1 Identify (P) in the following reaction:

H / H 2O
+2    (P)

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

Q.2 The reaction of E-2-butene with CH2I2 and Zn–Cu Couple in either medium leads to formation of

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

H SO NBS
Q.3 2 
4  P (Major)  Q (Major)

The structure of Q is

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

18

(i ) CH COO OH
Q.4  3   X
(ii ) H3O

The probable structure of ‘X’ is

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

Br2 NaI
Q.5 

 
P(Alkene)   Q (Alkene)
CCl 4 Acetone

Alkene (P) & (Q) respectively are

(A) Both (B) ,

 (C) Both (D) Both

Q.6 O-xylene on ozonolysis will give

O CH 3  C  O O
CHO || ||
(A) | & CH 3  C  CHO (B) | & CH 3  C  CHO
CHO CH 3  C  O

CH 3  C  O O
CH 3  C  O CHO || CHO
(C) | & | (D) | , CH 3  C  CHO & |
CH 3  C  O CHO CH 3  C  O CHO

O O (1eq )
s 4
Q.7   X.
H 2O / Acetone

Identify ‘X’.

(A) (B)

(C) (D) Reaction will not occur

PdCl ,HOH
Q.8 2
   Z.
CuCl 2 ,O 2

Identify Z.

(A) (B)

(C) (D) All are correct

CH 3 CH3
| | OsO4 (1equiv.)
Q.9 CH3  C  C  CH 2  CH  CH 2    A ; Identify A
( Acetone / water)

CH 3 CH 3 OH OH CH 3 CH 3
| | | | | |
(A) CH 3  C  C  CH 2  CH  CH 2 (B) CH 3  C — C  CH 2  CH  CH 2
| |
OH OH
 CH 3 CH 3
| |
(C) CH 3  CH — C  CH 2  CH  CH 3 (D) Reaction will not occur
| |
OH OH

Q.10 1-Penten-4-yne reacts with 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

Q.11 Compound (A) on oxidation with hot KMnO4 / OHr gives two compound
O
||
CH 3  CH  COOH & CH 3  C  CH 2CH 2CH 3
|
CH 3
compound A will have structure.
(A) CH 3CH 2  C  C  CH 2 CH 3 (B) CH3  CH  CH  C  CH 2CH 2CH 3
| | | |
CH 3 CH 3 CH 3 CH 3

(C) CH 3CH  C  C  CH 3 (D) CH3  CH  C  C  CH  CH 3

| | |
CH 3 CH3 CH 3

Q.12 alcoholic
  KOH  product


Major product is:

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

Q.13 Dehydration of 2, 2, 3, 4, 4–pentamethyl–3–pentanol gave two alkenes A and B. The ozonolysis
products of A and B are -
O
||
(A) A gives (CH 3 )3 C  C  C(CH 3 )3 and HCHO

O
||
B gives CH 3  C  CH 2  C(CH 3 )3 and HCHO

O
||
(B) A gives (CH 3 )3 C  C  C(CH 3 )3 and HCHO
 O CH 3
|| |
B gives CH 3  C  C  C(CH 3 )3 and HCHO
|
CH 3

O
||
(C) A gives (CH 3 )3 C  C  CH (CH 3 ) 2 and HCHO

O
||
B gives (CH 3 )  CH 2  C  C(CH 3 )3 and CH3CH2CHO
(D) None of these

O
||
Q.14 Alkene A O
3 / H 2O
 CH 3  C  CH 3 + CH3COOH + CH 3  C  COOH
||
O
A can be –
C(CH 3 ) 2
||
(A) (B) CH3  C  CH  HC  CH 3
(C) Both correct (D) None is correct

Q.15 reagent R reagent R

  2  1 

R1 and R2 are –
(A) Cold alkaline KMnO4, OsO4/H2O2 (B) Cold alkaline KMnO4, HCO3H
(C) Cold alkaline KMnO4, CH3–O–O–CH3 (D) C6H5CO3H, HCO3H

Con . H SO O 3 / H 2O / Zn
Q.16 + CH3MgBr H
3O
 A  24  B    C
A, B and C are –
A B C

(A)

(B)
 (C)

(D)

Q.17 An organic compound of molecular formula C4H6, (A), forms precipitates with ammoniacal silver
nitrate and ammoniacal cuprous chloride. ‘A’ has an isomer ‘B’, one mol of which reacts with one mol
of Br2 to form 1, 4-dibromo-2-butene. Another isomer of A is ‘C’, one mole of C reacts with only 1
mol. of Br2 to give vicinal dibromide. A, B & C are
(A) CH3–CH2–CCH and CH2=CH–CH=CH2 ;
(B) CH3–CC–CH3 and CH3–CH=C=CH2 ; CH3–CC–CH3
CH 2  CH
(C) C=CH2 and | || ; CH2 = CH–CH=CH2
CH 2  CH

(D) CH3–CC–CH3 and ; CH2 = CH–CH = CH2

CHCOOH
Q.18 CH2=CH–CH=CH2 + | | 
 product X by reaction R. X and R are
CHCOOH

(A) Diels Alder (B) Friedel-Crafts

(C) Diels Alder (D) Friedel-Crafts

Q.19 For the ionic reaction of hydrochloric acid with the following alkenes, predict the correct sequence of
reactivity as measured by reaction rates:
(I) ClCH=CH2 (II) (CH3)2.C=CH2 (III) OHC.CH=CH2 (IV) (NC)2C=C(CN)2
(A) IV > I > III > II (B) I > IV > II > III (C) III > II > IV > I (D) II > I > III > IV
CH 3 C NH 2
||
Q.20 Br Mg
 /
dry ether
 (X)     (Y) O

The structures of (X) and (Y) respectively are

(A) X = MgBr ; Y= OH
 (B) X = ; Y=

(C) X = MgBr ; Y=

(D) X = BrMg MgBr ; Y = HO OH

MULTI CORRECT ONE OR MORE THEN CORRECT (+4, -1)

Q.21 Re agent R Re agent R

2
   1 
  

R1 and R2 are:
(A) cold alkaline KMnO4, OsO4 / H2O2 (B) OsO4 / NaHSO3 ; Ag2O , H3O

(C) cold alkaline KMnO4, C6H5CO3H / H3O (D) C6H5CO3H ; OsO4 / NaHSO3

A
Q.22 Ph  C  CH 3  Ph–CH2–CH3
||
O
A could be:
(A) NH2NH2, glycol/OH– (B) Na(Hg)/conc. HCl
(C) Red P/HI (D) CH 2  CH 2 ; Raney Ni – H2
| |
SH SH
Q.23 Ph–CH=CH2 + BrCCl3 peroxide
 
Product is:

(A) (B)

(C) (D)

—
Q.24 OH

The above compound undergoes ready elimination on heating to yield which of the following products?
 (A) (B) (C) (D)

Q.25 Select true statement(s):

(A) I2 does not react with ethane at room temperature even though I2 is more easily cleaved homolytically
than the other halogens.
(B) Stereochemical outcome of a radical substitution and a radical addition reaction is identical.
(C) The rate of bromination of methane is decreased if HBr is added to the reaction mixture.
(D) Allylic chloride adds halogens faster than the corresponding vinylic chloride.
Q.26 Indicate among the following the reaction not correctly formulated.
SO Cl
(A) CH2=CH–CH3   CH2Cl–CHCl–CH3
2 2
UV light

(B) HCCH+CH2N2 

(C) (CH3)3CH + Cl2 photo

   (CH3)3C–Cl as major product
halogenati on

Na
(D) CH3–CC–CH2–CH2–CH3  
in NH (liq ) 3

Q.27 List I List II

( i ) BH
(A) CH3  C  CH 2   3 (1) CH3–CH2–CH=CH2
(ii ) H 2O 2 / OH
|
CH 3
(i ) Hg ( OAc) / HOH
2
(B) CH3  C  CH 2      (2) CH3–CH=CH–CH3
(ii ) NaBH4
|
CH 3
Cl
|
(C) CH 3  CH 2  CH  CH 3 CH ONa / 
3   (3) CH3  CH  CH 2OH
|
CH3
Cl OH
| ( CH 3 )3 CONa
|
(D) CH 3  CH 2  CH  CH 3     (4) CH 3  C  CH 3

|
CH 3
Codes: A B C D
(a) 4 3 1 2
(b) 4 3 2 1
(c) 3 4 2 1
(d) 3 4 1 2
Q.28 The incorrect statement regarding the product of reaction
Br2
A 
 B
CCl 4
(A) A is trans and B is a meso compound if R = R'
(B) A is trans and B is a racemic mixture if R  R'
(C) A is trans-alkene and B is always racemic mixture irrespective of the face whether R and R' are the
same or different.
(D) B is optically inactive due to external compensation if R  R' and optically inactive due to internal
compensation if R=R'.

Q.29 Which is B in the sequence HBr

 A (
i ) Mg / ether
  B
40C
( ii ) CO 2 / H 3 O

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

Q.30 Which will show geometrical isomerism.

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

Q.31 is diastereomers of

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

 ANSWER
1. A 2. B 3. C 4. A
5. C 6. A 7. B 8. A
9. B 10. D 11. B 12. A
13. B 14. C 15. B 16. A
17. A 18. A 19. D 20. C
21. B, C 22. A, B, C, D 23. A, C 24. B,C, D
25. A, C, D 26. A, C, D 27. C 28. C
29. B 30. A, B, C 31.