MASTERING CHEMISTRY 1

NBS GURUKUL
REVISION TEST SERIES
TARGET – IIT/AIPMT/AIEEE - 2009
CHEMISTRY
ORGANIC
Prof. Adarsh Bhatti
M.Sc. (Gold Medalist )
5 6
Solution : 4 1
1. (d) HO ¾ N COOH
3 2

4-Hydroxyimino cyclohexane-1-carboxylic acid

2. (b) 2-Methylpropane (Isobutane) º 1, 1-Dimethylethane
H3C ¾ CH ¾ CH3
½
CH3
CH3 CH3
H
H H H

H3 C H H3C H

H H
Most Stable Least Stable
2 H3C . H = 2 × 5.85 = 11.70 kJ
1 H . H = 1 × 4.18 = 4.18 kJ
15.88 kJ
æ 30 ö æ 30 ö
3. (b) As there is 30% racemisation, the given mixture contains ç 70 + ÷ % dextro-isomer and ç ÷ % l- isomer.
è 2 ø è 2 ø
o
85 ´ 10 o 15( -10 )
\ Specific rotation of mixture = + = 7o
100 100
4. (d) H2 C
H H2C
H2 C C H2C CH
½
O Remove Oxygen H2C CH
¾¾¾¾¾¾®
O atoms & join CH2
Double bond Cyclohexene
H2 C C
CH2 H
Hexane-1, 6-dial
5. (c)
H3CCO
O Cl O Cl -
½ ½
H3C ¾ C ¾ Cl + Al ¾ Cl ¾® H3C ¾ C+ Cl ¾ Al ¾ Cl
½ ½
Cl Cl
6. (a) A is meso -1, 2-butandiol, formed by, Syn addition.
The rule is
Cis alkene + Syn addition = Meso
Cis alkene + anti addition = Racemic
Trans alkene + Syn addition = Racemic
Trans alkene + anti addition = Meso
7. (a) Meso = Syn addition

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 MASTERING CHEMISTRY 2
8. (c)
+ dry ether
+ Ph3 P¾ CHR ¾¾¾® + Ph3 PO
THF

O CHR This is wittig Reaction.

9. (a)
H OOC
OH

O2 N
CH

OH
- COOH and – OH (Phenolic) groups are deactivated by – NO2 group
10. (c)
HO H H3 C
OCOCH3
P = H2 C = C Q = O COCH3
CH3 HO H

¾ CH3COOH H2O/H+ ¾ CH3 COOH H2O/H+

O¾H O¾H
½ ½
H2C = C ¾ CH3 H3C ¾ CH = CH

O O

H3C ¾ C ¾ CH3 H3C ¾ CH2 ¾ C ¾ H

Ketone Aldehyde \ These can be distinguished by Fehling solution.
11. (b) This is Cannizzaro’s reaction
12. (b)
+ -
HOH
Ph ¾¬ C º C ¾¬ CH3 ¾¾¾¾¾® Ph ¾ CH = C ¾ CH3 Ph ¾ CH2 ¾ C ¾ CH3
Hg2+/H+ ½
H¾O O
13. (d) trans-but-2-ene
14. (b)
CH3 CH3 CH3

KNH2/liq NH3 H ¾ NH2

¾¾¾¾¾® ¾¾¾¾® NH2
H - KCl
Cl - NH3
15. (a) Q it is highly ionic.
16. (b)
NH2 N2+Cl- OH ONa+ O ¾ C2H5
NaNO2/HCl NaOH(aq) NaOH(aq) C2H5I
¾¾¾¾¾® ¾¾¾¾® ¾¾¾® ¾¾¾®
0 – 5oC - NaI
(X) (Y) Phenetole
..
17. (c) H3C ¾ CH2 ¾ CH2 ¾ CH2 ¾ N H 2
I
n-Butyl amine

NBS GURUKUL , SCF 5 Market Guru Teg Bahadur Nagar Jalandhar –144003 , Ph.No. 5072918, M.No. 98141 - 02308
 MASTERING CHEMISTRY 3
CH3
½
H3C ¾ CH ¾ CH2 ¾ CH3 H3C ¾ CH ¾ CH2 ¾ NH2 H3C ¾ C ¾ NH2
½ ½ ½
NH2 CH3 CH3
II III IV
Sec. Butyl amine Iso butyl amine Tert. Butyl amine
The order of basic nature of amines is I > II > III > IV
As the steric hinderance increases from I to IV, stability of corresponding conjugate acids decreases and hence the basicity
decreases accordingly.
18. (b) NHCOCH3 NH2 NH3
(i) Br2/CH3COOH Br Br
¾¾¾¾¾¾¾¾® +
(ii) H2O/H+
o- p–
Bromoaniline
H3C sp3 CH3
19. (d) H3C ¾ H2C ¾ N : : N ¾ CH2 ¾ CH3
H3C ¾ H2C ¾ H2C CH2 ¾ CH2 ¾ CH3
This interconversion is called as nitrogen or amine inversion.
20. (a)
CHO CH = N ¾ NH C6H5
CHO ½
½ C = N ¾ NH C6H5
CHOH ½
½ 3C6H5NHNH2 (CHOH)3
(CHOH)3 ¾¾¾¾¾® ½
½ - 2 H2O CH2OH
CH2OH - NH3 Glucosazone
- C6H5 NH2
21. (d) 130
22. (c) n H2C = CH Polymerises ¾ H2C ¾ CH ¾
½ ¾¾¾¾¾® ½
CN CN n
Acrylonitrile Polyacrylonitrile
(PAN)
23. (a) Let ratio of A : B = a : b
a
Amount of A =
a+b
b
Amount of B =
a+b
Specific rotation of A = + 20o
Specific rotation of B = - 20o
a b
× 20 - × 20 = 10
a+b a+b
a-b 10 1 a 3
= = 2a – 2b = a + b 2a – b = b + 2b a = 3b =
a+b 20 2 b 1
24. (b) Free Radical mechanism
25. (d) CaC2 + H2O ¾¾® Ca (OH)2 + C2H2
HC º CH + 2 [Ag (NH3)2] OH ¾¾® AgC º C Ag ¯ + 4NH3 + 2H2O
White ppt.
26. (b) An optically inactive compound.
27. (b)
O O
O3/CCl4 O Zn/H2O
¾¾¾¾® O ½ ¾¾¾¾¾¾® º
O -H2O2
O O

NBS GURUKUL , SCF 5 Market Guru Teg Bahadur Nagar Jalandhar –144003 , Ph.No. 5072918, M.No. 98141 - 02308
 MASTERING CHEMISTRY 4
28. (c) NH3 being strong nucleophilic causes elimination in stead of substitution, in case of alicyclic

compounds.
29. (c)
Cl -H2O Cl Cl
H ¾ C ¾ Cl ¾¾¾® H : C ¾ Cl ¾¾¾® : C
Cl Cl Cl
OH-
30. (a)
O + O MgBr O _ +
CH3MgBr ½ H3CMgBr
H3C ¾ C ¾ OC2H5 ¾¾¾¾¾® H3C ¾ C ¾ OC2H5 ¾¾¾¾¾¾¾® H3C ¾ C ¾¾¾¾®
½ - Mg(OC2H5)Br ½
CH3 CH3
H OH
O MgBr OH
½ H2O/H+ ½
H3C ¾ C ¾ CH3 ¾¾¾¾¾® H3C ¾ C ¾ CH3
½ ½
CH3 CH3
Tert Butyl alcohol
Cl2 KOH (alc.)
31. (c) H3C – CH2 – COOH ¾¾¾¾® H3C ¾ CH ¾ COOH ¾¾¾¾¾¾® H2C = CH – COOH
Red p ½ - KCl Acrylic acid
HVZ Cl - H2O
reaction
O O OH O O
OH- ½ D
32. (a) H ¾ C ¾ H + H ¾ CH2 ¾ C ¾ CH3 ¾¾¾¾® H ¾ C ¾ CH ¾ C ¾ CH3 ¾¾¾® H2C = CH ¾ C ¾ CH3
Formaldehyde Acetone ½ ½ -H2O
H H Methyl vinyl ketone
33. (c) Cannizzaro’s reaction
H

34. (c) O-
O-
MeO
Electron releasing – OMe groups makes groups makes it best hydride donor in the given options.
35. (b) CHO OH_ COO-
½ ¾¾¾® ½
CHO CH2OH
This is Internal Cannizzaro’s reaction.
36. (a) Cope reaction
37. (a) CH3 CH3
HNO3 (conc) NO2
¾¾¾¾¾®
H2SO4 (conc)

NO2 NO2
p-Nitrotoluene
In Electrophilic substitution reactions – NO2 is meta directing and – CH3 go. Is o-directing in nature
38. (d) NH2 NH2 N2Cl-
3Br2 Br Br NaNO2 Br Br H3PO2 Br Br
¾¾® ¾¾¾¾® ¾¾¾¾®
-3HBr HCl
Aniline
Br Br Br
NO2 NH2 N2Cl-
39. (b) NHO3/H2SO4 Zn/HCl NaNO2/HCl H3PO2 /H2O
¾¾¾¾® ¾¾¾® ¾¾¾¾¾® ¾¾¾¾¾®

NBS GURUKUL , SCF 5 Market Guru Teg Bahadur Nagar Jalandhar –144003 , Ph.No. 5072918, M.No. 98141 - 02308
 MASTERING CHEMISTRY 5
40. (c) Insulin is a Protein Harmone.
41. (c) Kwashiorkar is a protein deficiency disease.
Polymerises
42. (d) n FClC = CF2 ¾¾¾¾¾¾® ( - FCl – CF2 - )n
Chlorotrifluoro ethane Polychlorotrifluoro ethane
(PCTFE)
Br2 2Na NH2
43. (c) C6H5 – CH = CH2 ¾¾® C6H5 ¾ CH ¾ CH2 ¾¾¾¾¾®
½ ½ - 2 NaBr
Br Br - 2 NH3
(A)
NaNH2
C6H5 – C º CH ¾¾¾®

CH3I
C6H5 – C º C- Na+ ¾¾¾® C6H5 – C º C – CH3
- NaI (B)
44. (d) CH3 CH3
H+ H2O CH3 Ring expansion
CH3 ¾¾® CH3 ¾® CH3 ¾¾¾¾¾¾®
+

OH : O H OH : O H2 OH
.. .+

CH3 CH3 CH3

H+
Å CH3 ¾¾¾¾¾® CH3 CH3

OH O O
45. (a) More steric hinderance with two alkyl groups on the same carbon in (b) and lesser is the reactivity. More substituted alkenes are
more stable.
\ (c) & (d) are not possible.
46. (b) Inversion of configuration takes place due to SN2 mechanism.
47. (a)
+ Br2 CH2Br
CH2 + HO Br ¾¾¾¾®
(from) H2 O OH
Br2/H2O
48. (c) It does not react even at high temperature because it has no ortho hydrogen
Cl
H3C CH3

H OH
H- H Hydride shift OH
49. (d) ¾¾® ¾¾¾¾® ¾¾®

Ph Ph Ph
Ph
2o carbocation
50. (d) Both (a) & (b)

NBS GURUKUL , SCF 5 Market Guru Teg Bahadur Nagar Jalandhar –144003 , Ph.No. 5072918, M.No. 98141 - 02308