4 DPP20to55

COMPLETE COURSE IN ORGANIC CHEMISTRY
BY VINEET KHATRI SIR

CLASS : XI TIME : 35 MIN. DPP. NO.20
O
||
1. CH3 – CH2–CH–C—OCH3
|
C2H5
(A) Methyl 2-ethylbutanoate (B) 1-methoxy-2-ethylbutanone

(C) 3-Methoxycarbonylpentane (D) 1-methoxy-2-ethylbutanal
O
||
2. CH3 – CH=CH–C—OH
(A) But-1-en-4-oic acid (B) 1-hydroxybut-2-en-1-one

(C) But-2-en-1-oic acid (D) But-2-en-4-oic acid
OCH3
3. |
CH3 – CH=C –— CH3
(A) 1-Methoxy-1-methylpropene (B) 2-Methoxybut-2-ene

(C) dimethylpropeneether (D) None of these
Me O
4. | ||
CH2 = C — C — OC2H5
(A) Ethyl 2-methylprop-2-enoate (B) Ethyl 2-methylprop-1-enoate

(C) 1-Ethoxy-2-methylprop-2-enone (D) 1-Ethoxy-2-methylprop-2-enal
CH3 CH3
5. | |
CH3 – CH — CH — CH2NH2
(A) 2, 3-Dimethylbutan-4-amine (B) 2, 4-Dimethylbutan-1-amine

(C) 2, 4-Dimethylbutan-4-amine (D) 2, 3-Dimethylbutan-1-amine
O
||
CH3 – C — CH — CH — CH3
6. | |
C2H5 CH3
(A) 3-(Methylethyl)pentan-2-one (B) 3-(Methylethyl)pentan-4-one

(C) 3-Ethyl-4-methylpentan-2-one (D) 3-Ethyl-2-methylpentan-4-one
O
||
CH3 – CH — CH2 — C — Br
7. |
CH3
(A) 2-Methylbutanoyl bromide (B) 2-Methylbutan-4-oyl bromide

(C) 1-Bromo-3-Methylbutanone (D) 3-Methylbutanoyl bromide
8. CH 3 – CH — CH 2 — OH
|
C 6H 5
(A) 2-Phenylpropan-1-ol (B) 2-Phenylpropan-3-ol

(C) 1-(2-Hydroxy-1-methylethyl)benzene (D) 1-((Hydroxymethyl)ethyl)benzene
CH3
|
9. CH3 — C —— CH — CH — CH2 — CH3
| | |
CH3 CH3 I
(A) 3-lodo-4, 5, 5-trimethylhexane (B) 4-lodo-1, 1, 3-trimethylhexane

(C) 4-lodo-2, 2-dimethylheptane (D) 4-lodo-2, 2, 3-trimethylhexane
CH3
|
10. CH3 — CH2 — CH — CH — C — CH3
| | |
Cl CH3 OH
(A) 4-Chloro-2, 3-dimethylhexane-2-ol (B) 4-Chloro-2-hydroxy-2, 3-dimethylhexane

(C) 4-Chloro-1, 1, 2-trimethylpentan-2-ol (D) 3-Chloro-2, 3-dimethylhexane-2-ol
1.
(A) 2-Methylbutan-3-one (B) 3-Methylbutan-2-al

(C) 2-Methylbutan-3-al (D) 3-Methylbutan-2-one
CH3 – CO
2. O
CH3 – CH2 – CO
(A) Ethanoic propanoic anhydride (B) Propanoic ethanoic anhydride

(C) 1-Ethanoyloxypropanone (D) 3-Ethanoyloxypropan-3-one
3. CH 3 – C –– C – CH 3
|| ||
O O
(A) Butane-2, 3-dial (B) Butane-1, 3-dione

(C) Butane-2, 3-dione (D) 1, 2-dimethylethanedione
4. CH 2 = CH – CH = CH 2
(A) Butane (B) Buta-1, 3-diene (C) Butane-1, 3-diene (D) none of these
5. CH2 — CH2 –– CH2

| |
COOH COOH
(A) Pentane-1, 5-dioic acid (B) Pentane-1, 5-dicarboxylic acid

(C) Propane-1, 3-dioic acid (D) None of these
CH2Cl
|
6. CH2 — CH — CH2
| |
Cl Cl
(A) Tris(chloromethyl) methane (B) 1, 3-Dichloro-2-(chloromethyl) propane

(C) 1-Chlorobis(chloromethyl) ethane (D) None of these
CH3
|
7. CH3 — CH — CH — CH — C — CH3
| | | |
OH CH3 OH CH3
(A) 3, 5, 5-Trimethylhexane-2, 4-diol (B) 2, 2, 4-Trimethylhexane-3, 5-diol

(C) 1, 2,4, 4-Tetramethylpantane-1, 3-diol (D) 2, 2,4, 5-Tetramethylpantane-3, 5-diol
8. HOOC — CH = CH — COOH
(A) But-2-ene-1, 4-dicarboxylic acid (B) But-2-ene-1, 4-dioic acid
(C) Ethene dicarboxylic acid (D) Ethene dioic acid
OCH3
|
9. CH3 — CH — CHO
(A) 1-formyl-1-methoxyethane (B) 2-Methoxypropan-3-one

(C) 2-Methoxypropanal (D) 2-Methoxypropan-3-al
CH3
|
10. CH2 = C — COOCH3
(A) Methyl-2-methylprop-1-en-3-oate (B) 2-Methoxycarbonylpropene

(C) 2-Methoxycarbonylprop-2-ene (D) Methyl-2-methylprop-2-enoate
11. CH 3 — CH = CH — COOH
(A) But-2-ene-1-oic acid (B) But-1-ene-1-oic acid

(C) But-2-ene-1-carboxylic acid (D) Propene-1-carboxylic acid
12. (CH 3) 3C . CH 2CH 2Cl
(A) 2,2-Dimethyl-4-chloro butane (B) 1-Chloro-3, 3-dimthylbutane

(C) 4-Chloro-2,2-dimethyl butane (D) None of these
13. CH3 — CH — CH — CH — CH3

| | |
Cl Br OH
(A) 3-Bromo-4-chlorpentan-2-ol (B) 3-Bromo-2-chloro-4-hydroxypentane

(C) 3-Bromo-2-chloropentane-4-ol (D) None of these
Br Cl
| |
14. CH3 — CH2 — C — CH — CH2 — Cl
|
OH
(A) 3-Bromo-4, 5-dichloropentan-3-ol (B) 3-Bromo-1, 2-dichloro-3-hydroxypentane
(C) 3-Bromo-1, 2-dichloropentan-3-ol (D) 3-Bromo-4, 5-dichloro-3-hydroxypentane
15. CH3 — CH — CH2 — O — C2H5

|
OH
(A) 1-Ethoxypropan-2-ol (B) 3-Ethoxypropan-2-ol

(C) 1-Ethoxy-2-hydroxypropane (D) None of these
OH
O
1.
(A) 2, 6-Dimethylhepta-2, 5-dienoic acid (B) 3, 7-Dimethylhepta-2, 5-dienoic acid

(C) 1-Hydroxy-2, 6-dimethylhepta-2, 5-dienone (D) None of these
2. CHO
(A) 3-Methylpent-1-en-4-al (B) 3-Methylpent-4-enal

(C) 3-Methylpent-4-carbaldehyde (D) 3-Methyl-5-oxopent-1-ene
3. Name the following halides according to IUPAC system and classify them as alkyl, allylic, benzylic (primary,
secondary, tertiary), vinylic or aryl halides :
(i) (CH3)2CHCH(Cl)CH3 (ii) CH3CH2CH(CH3)CH(C2H5)Cl
(iii) CH3CH2C(CH3)2CH2I (iv) (CH3)3CCH2CH(Br)C6H5
(v) CH3CH(CH3)CH(Br)CH3 (vi) CH3C(Cl)(C2H5)CH2CH3
(vii) CH3C(C2H5)2CH2Br (viii) CH3CH = C(Cl)CH2CH(CH3)2
(ix) CH3CH = CHC(Br)(CH3)2
4. Give the IUPAC name of the following compounds :

(i) CH3CH(Cl)CH(Br)CH3 (ii) CHF2CBrClF
(iii) ClCH2C  CCH2Br (iv) (CCl3)3CCl
5. Write the structure of the following organic halogen compounds.

(i) 2-Chloro-3-methylpentane (ii) 4-tert-Butyl-3-iodoheptane
(iii) 1, 4-Dibromobut-2-ene.
6. Write IUPAC names of a following compounds :
CH3
|
(i) CH3 – CH – CH – C – CH3 (ii) CH3 – CH – CH2 – CH – CH – CH2CH3
| | | | | |
CH3 OH CH3 OH OH C2H5
(iii) CH3 – CH – CH – CH3 (iv) HOCH2 – CHOH – CH2OH

| |
OH OH
(v) CH3 – O – CH2 – CH – CH3 (vi) CH3 – CH2 – O – CH – CH2 – CH3
| |
CH3 CH3
7. Write structures of the compounds whose IUPAC names are as follows :

(i) 2-Methylbutan-2-ol (ii) 3, 5-Dimethylhexene-1, 3,5-triol
(iii) 1-Ethoxypropane (iv) 2-Ethoxy-3-methylpentane
(v) Cyclohexylmethanol (vi) 3-Cyclohexylpentane-3-ol
(vii) Cyclopent-3-en-1-ol (viii) 3-Chloromethylpentan-1-ol.
1. Name the following compounds according to IUPAC system of nomenclature :

(a) CH3CH(CH3)CH2CH2CHO
(b) CH3CH = CHCHO
(c) CH3CH(CH3)CH2C(CH3)2COCH3
(d) CH3CH2COCH(C2H5)CH2CH2Cl
(e) CH3COCH2COCH3
(f) (CH3)3CCH2COOH
2. Draw the structures of the following compounds :

(a) 3-Methylbutanal
(b) 4-Chloropentan-2-one
(c) 4-Methylpent-3-en-2-one
(d) 3-Bromo-2-phenylpentanoic acid
(e) Hex-2-en-4-ynoic acid
3. Write the IUPAC names of the following ketones and aldehydes. Wherever possible, give also common
names.
(a) CH3CO(CH2)4CH3
(b) CH3(CH2)5CHO
CHO
(c)
(d) CH3CH2CHBrCH2CH(CH3)CHO
4. Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary
amines.
(i) (CH3)2 CHNH2
(ii) CH3(CH2)2NH2
(iii) CH3NHCH(CH3)2
(iv) (CH3)3CNH2
(v) (CH3CH2)2NCH3
1. Write the IUPAC name of the following compound: [CBSE-: 2004]
CH2 — CO — CH2 — CH2 — CH2 — Cl

|
CH3
2. Write the IUPAC name of: CH3 . CH (Br) CH2CONHCH3. [CBSE-: 2006]
3. Write the IUPAC name of the compound: [CBSE-: 2007]
CH3 — CH — CO — CH — CH3
| |
CH3 CH3
4. Name the following compound according to IUPAC system: [CBSE-: 2007abroad]
CH3COCH2COCH3
5. Write the IUPAC name of the following compound: [CBSE-: 2008]
H3C — CH — CH2 — CH — CH — CH2OH

| | |
CH3 OH CH3
6. Give the IUPAC name of the following compound: [CBSE-: 2009]
CH3 — C = C — CH2OH
| |
CH3 Br
7. Write the structure of 3-oxopentanal. [CBSE-: 2009]
8. Give the IUPAC name of H2N . CH2 . CH2 . CH = CH2. [CBSE-: 2010]
9. Draw the structural formula of 1-phenylpropan-1-one molecule. [CBSE-: 2010]
10. Write the IUPAC name of the following compound: CH2 = CHCH2Br. [CBSE-: 2011]
11. Draw the structure of 4-chloropentan-2-one. [CBSE-: 2011]


OLYMPIAD LEVEL PROBLEMS
S.No. Compounds Write IUPAC - Name
1. H3C CH3
HN O
CH3
O CH3
2.
H2N
Br CH3
O
3.
H2N Cl
Br CH3
O
4.
H2N Cl
H2N
5.
CH2
6.
H2N CH3
CH
O
CH3
7.
H2N
CH2
O
CH3
H2N
8.
HC
O
CH3
9.
H2N
Br
O
10. H3C
O
Cl
Cl
O
11. H3C
O
Br
12. H3C CH3

O
13. H2C CH3

O
O O
14. H3C CH3

O O
H3C O O
15. CH3
O O
O
CH3
16.
O
17. H3C
NH2
CH3 O
18.
O O CH3
19. H3C CH3

O
20.
H3C O CH3
H3C CH3
21.
NH2
NH2
H3C CH3
22.
Br

O OH
1.
HO
F
HC
F F
2. O
S
HO O O
HO
3. H2C
OH
HO O
4. Cl SH
CH3
O S O
OH
5.
HO
O
HO
O CH3
O OH
6. H2C
H2N
CH3
OH
O S O
OH
O OH
7.
H3C
CH3
HC
CH3
CH3
NH2
- O OH
O +
O
N
Cl
8. Cl
O S O
CH2
OH
O OH
H3C CH3
9. O
O
CH3
HO
O
O CH3
10.
H3C
CH3
OH O
11. O
O
OH
12. HO
CH3
HO O
O OH
H2C
CH2
13.
H3C SH
O
+
N -
H3C O
O S O
14.
H2C OH
HO O
HC
HO
Cl
O OH
15. Br
O CH2
CH3

H N H2N
2
H3C CH3
1.
CH3 OH
NH2 OH
O
H3C
2. OH
HO O
3. H3C
OH
Cl O
4.
O NH2
O
H3C
OH
O
Br
O
H3C
5.
OH
O O
CH3
CH3
Cl
Cl Cl
O
6. H3C
O OH
NH
CH3
O NH2
O
7.
H3C
OH
Cl O
OH
O S O
O
8. H3C
OH
9. H3C
CH3
O
OH
N S
O
H3C
H3C
H2C O O
10.
CH3
HO O
N
11.
H3C
Cl O
H3C
12.
O CH3
O
13. H3C
O S O
HO O
O
OH
14.
15.

O
Cl
1.
N
H3C
2.
H3C
3.
O
O CH3
O
4. CH3
O
5. H3C
O O
6.
O
O
CH3
7. O
Cl
8.
O
9.
OH
10.
Cl
N
11.


O
1. H3C
OH
Cl O
N
O
H2C
2.
OH
O O
CH3
CH3
3. O O
O
H3C
HO OH
H3C
O O
4.
H3C
OH
Cl O
5. O CH3
H3C O
6.
O Cl
NH2
O
7.
CH3
H3C
NH CH3
OH
O
8. H3C
HS H2N OH

NH2
H3C
1. CH3
Br Br
CH3
H3C
2. NH2
CH
3. H3C CH3
H2N
CH2
H3C CH3
4. NH2
H2N Br
5. H3C
CH3
Cl
CH2
HC
6.
H2N
CH3
H2N
CH3
7.

CH3
1.
O O
O
CH3
CH3
2. O
O CH3
O
H3C
3.
O O
O
CH3
H3C
4.
O O
O
CH3
CH3
O O
5.
O CH3
Br
Cl
CH3
O O
6.
O
Br
H3C
7.
O O
O CH3
CH3
O O
8. CH3
O
H2C O
9. O
CH3
CH2
O O
10.
O CH3
CH2
11.
O O
O
CH3
CH
12. O O CH3
O
CH2
13. O O
O
HC

1.
Cl NH Br
O
2.
NH Cl
Br
H3C NH
3.
CH3
4.
H2N CH3
5. H3C CH3
NH
6. H2N
CH2
7. H3C
NH CH3
Cl
Br
8.
H3C NH CH3
O
H3C
9. NH
CH
10. O
H3C O
O
11.
12. H3C NH2
13. H3C CH2
NH2
Br
14.
H3C CH3
H2N

H3C CH3
NH2
1.
HO O
Cl
H3C CH3
NH2
2.
HO O
HO
O S O
H3C CH3
3.
HO O
H2C
H3C
HO CH3
4.
O S O
O
OH
HO
O S O
5. H3C CH3
NH2
CH3
H3C
6.
NH2 CH3
CH3
7. O
O HO
CH3
H3C
8.
O Cl O
H3C
H3C CH3
9.
O Cl O
H3C
CH3
10.
Cl O
H3C CH3
CH2
11. O S O O
CH3
OH
HO O
S
O CH3
12.
O
H3C
H3C
O O
13. H3C CH3
NH2
CH3
H3C
14. Cl Cl
HO O
Cl

HO
O S O
H3C CH3
1.
H2N O
H3C CH3
2. O O O
CH3
CH3
O
CH3
3.
CH3
CH3
O
4. NH2
O
CH3
O OH
H3C
CH3
5. NH2
O S O
OH
CH3
O O
H3C
CH3
H2N
6.
O O
CH3
H3C
O O
7.
H3C N
O
CH3
CH3
NH
H3C CH3
8.
O O
HO
9.
O
CH3 CH2
O
10. H3C
NH2
CH3
F F
F
H3C CH3
O CH3
11.
HO S
O CH3
H3C CH3
O
H3C
NH CH3
12.
HC


HO
O S O
CH3
1.
O O
CH2 CH3
2. O OH
CH3
O O
CH3
3. O OH
O CH3
4. HO
O CH3
O
O
5. O
HO
S
O N
O OH
6.
H3C CH3
N
H3C
CH3
O
7. H3C
CH3
H2N O
HO
8.
CH
O
F CH3
F
O
9. F CH3
O
Cl O
Cl NH2
O
10. O
CH3
H2C
11. O OH
CH2
CH
HO
HC
O S O
12.
CH2
Cl O
HO
O
S
O O
13.
H3C Cl HO
Cl
HO
H2C
O S O
CH3
14.
Cl O CH2
H3C
15.
O S O
H2N O
OH
H3C CH3
CH3
16.
CH3
H3C CH3
17. Cl
O
Br
+
- N
O O

CH3
1.
CH3
2.
CH2
3.
CH
4.
5. CH2
6.
CH3
7.
CH3
8.


O
OH
1.
Cl
2.
O NH2
3.
O CH3
O
4.
O
CH3
O
5.
6.
7.
O
OH


CH3
CH3
1.
CH3
2.
CH3
3. CH3
Cl
4. Br
CH3
O
CH3
5.
O CH3
NH
6.
OH
O
OH
S
7. O
HO
8. CH3
O
O OH
Cl
9.
CH3
O
CH3
O
10.


HO
OH
1.
OH
2.
OH
3.
OH OH
OH
4.
Cl
OH
5.
Br
Br OH
6.
Cl
N
HO
7.
O
N
8. Br
OH
N
9.
O
O
CH3
-
O + O
N
10.
-
O + O
N
11.
Cl
Br

Br
Br
1.
+
- N
O O
Br
Cl
2.
+
- N
O O
Cl
Br
3.
+
- N
O O
OH
Br
4.
Cl
CH3
5.
Br
6.
Br
NH2
7. Br
Cl
NH2


O
1.
H3C O
O
2.
3.
HO
O
4.
Cl
Cl
5. Cl
Cl
Cl
6.
Cl
7.
Cl Cl
Br
8.
Cl Cl
Cl
9.
Cl Br
Cl
10.
Br


O
OH
1. O
O
CH3
2.
NH2
O
OH
3.
4.
O
CH3
O
O
5.
O CH3
6.
CH3
7.
8.


O
1.
OH
Cl
O
CH3
2. CH3
H3C
CH3
3. CH3
4.
OH
Cl O
+
N -
O
5.
NH2
6.
Br OH
7.
OH
8. O
OH


Br
N
1.
OH
O
2. OH
O O
CH3
O
3.
OH
O
CH3
O
4. Cl
O
O CH3
HO
NH2
5.
O
Cl O
6. NH2
7. O
8.
OH


O
OH
1. O
OH
2.
O
HO
3.
Cl
Cl
NH2
4.
CH3
F
F
5. F
O
+
N -
6. O
O
CH3
O
7.
O
8.
NH


O
NH
1.
O
H3C
NH
2.
NH
3.
Br
O
H3C
4. O
5. NH
O
6.
Br NH
Cl
7. O
Cl NH
Br

Q. Identify the type of inductive effect of atom or group which is directly attached to the cyclic system ?
CH O
1. Cl
10.
O
NH2
CH3
O
2. 11.
CH3
O
12.
3.
F
F
Cl
4. 13. F
OH
O
OH
5. S
14. O
CH3
6. N
15.
7. CH3
O 16.
OH
8. CH3
O
17.
CH3
O
9.

1. Identify + I or – I effect which is present by circled group ?
O
OH CH3
(a) (b) OH (c)
O
|| CCH NO2
(d) (e) (f)
NH3
(g) (h) CH3 – CH = CH2 (i) CH3 – C  CH
(j) H 2C = CH – C  CH (k) CD3 – CH = CH2
NH2
(l) (m) CH3 – CH2 (n) NO2 – CH 2 – CH 2
Cl SO3H
(o) Cl – CH2 – CH2 (p) (q)
CH3 CH3
(r) CH 3 –– CH3 (s) (t)
“Seize the first opportunity to Act upon every Resolution.”


Q. Circle-group shows inductive effect – I & I effect.
7. NH2
H3C O S O
1.
8. H2C
CH3
2.
9.
3. CH3 CH3
10. OH
O
P
O
HO
4. O
Cl
11.
O S O
5.
H3C
O
F
12.
F F
O S O
6. F
13. CH 21.
22.
14. OH
15.
SH
23. H3C
16.
Br
24.
CH3
17. O NH
Cl
25.
O NH2
CH3
18.
F
19. 26. O
F F N
20. 27.
N OH
O S O
- 37.
28. C H2C
+
N CH2
38. H3C CH2
H3C CH3
39.
CH3
CH3
O O
29. N
40.
O
O CH3
41.
30.
O
CH3
CH3
31. 42.
HC
32.
CH2 CH3
43.
CH3
33. H2C
O
H2C N
34.
44.
H3C O
35.
N
CH3
H2C
O
O 45.
36.
H2C NH2

1. Compare Stability
1. , 2. ,
NO2 NO2
3. , 4. ,
5. , 6. F – CH2 – CH 2 , Cl – CH2 – CH2
F
7. , 8. , O
O F
O
F O Cl O
9. O , 10. O ,
F Cl O
CH2 O O
11. 12. , || 
, CH3 – C – O
H O
O O O O
|| || || || 
  
13. CF3 – C – O , CCl3 – C – O 14. CHCl2 – C – O , O2N – CH2 – C – O
 O

15. , 16. ,
O
"Success comes through Dedication, Determination,

and Discipline & Desire."

Q. D raw resonance hybrid.
CH2
1.
12.
H2C
13. H3C
2. CH3
CH3
14. H2C CH2

3.
H2C
15.
4. H2C CH2

5.
16.
6.
CH2
H2C
17.
7.
8.
9. H2C CH2
18.
H3C CH3
10.
CH3
11.
H2C
19.
H3C
20.
29.
21.
30.
H2C
22.
23.
CH2
H + H
N
H 31.
24.
H
H +
P
H
25.
26.
27.
28.

Q. Draw the Resonating structure and Resonance Hybrid of following species ?

S.No. Compound Resonating Structure
1. -
H2C CH2
2. H3C
-
O
NH2
3.
-
CH
4.
NH2
5.
O
-
C
6.
-
CH
7.
8. -
O -
O
CH3
O
9.
Cl
10.
- CH3
11. H2C
12. H3C
NH2
-
CH
13.
-
CH
14.
H3C
O
15.
16. CH3
H3C
O
-
O
17.
18. H3C
OH

Q. Draw the Resonating structure and Resonance Hybrid of following species ?

S.No. Compound Resonating Hybrid
CH
1.
CH
2.
CH
3.
4.
HC
H2C CH
5. CH3
6.
H2C
CH3
7.
O
H2C
8.
O
O +
CH
9.
H
N +
10. CH
HO
+
11. CH
H3C
S +
CH
12.
+
13. C
OH
O
14. +
CH

1. Draw Resonance hybrid of the following compounds
1. 2.
NH2
3. 4.
–
OO
O
5. 6.
7. 8.
9. 10.
11. 12.
13. 14.
15. 16.
–
O
CH2
..
17. 18. H2 N  C  N:
NO2

19. NOO
3 20. O=C=O
21. 22.
23. 24.
25. 26.
–
O
27. 28.
–
29. 30. OO– C = O
–
OO
"What you get by reaching your destination is not nearly

important as what you will become by reaching your
destination.”

S.No. Resonting Structure Relative stability
OCH3 
O – CH3
1. ; 

O O

2. ;
O O O
||
3. CH3 – C – OH , CH3 – C– OH, CH3 – C = O– H
 
NH2 NH2 NH2

4. ; ;
5. O = C = O ; O  C – O ;
  +2
O = C – O ; O – C – O
O O
6. || ;  | ;
H – O – C – NH 2 H – O = C – NH2
O O
|  ; |

H – O – C = NH2 H – O – C – NH2

7. ;

 
O O O

8. ; ;

Answers of DPP No.- 20

1. A 2. C 3. B 4. A 5. D 6. C 7. D
8. A 9. D 10. A

1. D 2. A 3. C 4. B 5. A 6. B 7. A
8. B 9. C 10. D 11. A 12. B 13. A 14. C
15. A
1. A 2. B
3. (i) 2-chloro-3-methylbutane (ii) 3-chloro-4-methylhexane
(iii) 1-Iodo-2, 2-dimethylbutane (iv) 1-bromo-3, 3dimethyl-1-phenylbutane
(v) 2-bromo-3-methylbutane (vi) 3-chloro-3-methylpentane
(vii) 3-bromomethyl-3-methylpentane (viii) 3-chloro-5-methyl-hex-2-ene
(ix) 4-bromo-4-methyl-2-pentene
4. (i) 2-bromo-3-chlorobutane (ii) 1-bromo-1-chloro-1,2,2-trifluoroethane
(iii) 1-bromo-4-chloro-but-2-yne (iv) 1,1,1,2,3,3,3-heptachloro-2-trichloromethylpropane
Cl
Br
5. (i) (ii) (iii)
Br
I
6. (i) 2,2,4-trimethyl-3-pentanol (ii) 5-ethyl-2,4-heptanediol
(iii) 2, 3-butanediol (iv) 1, 2,3-propanetriol
(v) 1-methoxy-2-methylpropane (vi) 2-ethoxybutane
OH Et – O
OH
7. (i) (ii) (iii) O (iv)
OH OH
OH Cl
OH
(v) (vi) (vii) (viii)
OH HO

1. (a) 4-methylpentanal (b) But-2-enal (c) 3,3,5-trimethyl-hexan-2-one
(d) 6-chloro-4-ethyl-3-hexanone (e) 2, 4-pentanedione (f) 3,3-dimethylbutanoic acid
O Br
O Cl O
2. (a) (b) (c) (d) HO
O
C6H5
(e) HOOC – CH = CH – C  C – CH3
3. (a) 2-Heptanone (b) Heptanal
(c) Cyclopentane Carbaldehyde (d) 4-Bromo-2-Methyl Hexanal
4. (I) 2-Propanamine (II) 1-Propanamine

(III) N-Methyl-2-Propanamine (IV) 2-Methyl-2-Propanamine
(V) N-Ethyl-N-Methyl Ethanamine
2 3 4 5 6
1. CH2 – CO – CH2 – CH2 – CH2 – Cl
1|
CH3
6-Chlorohexan-3-one
2. CH3CHCH2CONHCH3
|
Br
3-bromo-N-methylbutanamide
1 2 3 4 5
3. CH3 – CH – CO – CH – CH3
| |
CH3 CH3
2, 4-dimethylpentan-3-one
O O
1 2|| 3 4|| 5
4. The IUPAC name of CH 3 – C – CH 2 – C – CH 3 is pentan-2, 4-dione.
6 5 4 3 2 1
5. H3C – CH – CH2 – CH – CH – CH2OH
| | |
CH3 OH CH3
2, 5-Di-methyl-hexane-1, 3-diol
6. 2 - Bromo-3-methyl-but-2-en-1-ol.
7. CH3 – CH2CO – CH2 – CHO
8. but-3-en-1-amine
9. The structural formula of 1-phenylpropan-1-one is
O
||
CH3 – CH2 – C
10. 3-bromopropene
O Cl
11.
Answer Key of DPP No. - 25

1. N-(1-methyl ethyl) ethanamide 2. hexanamide
3. 4-bromo-5-chlorohexanamide 4. 4-bromo-5-chlorohexanamide
5. but-3-enamide 6. 2-methylbut-3-ynamide
7. 3-cyclobutyl-5-methylhept-6-enamide 8. 2-ethylbut-3-ynamide
9. butanamide 10. chloromethyl 2-bromobutanoate
11. bromomethyl 2-chlorobutanoate 12. but-2-en-1-yl propanoate
13. butyl prop-2-enoate 14. diethyl ethanedioate
15. ethyl methyl ethanedioate 16. 1-cyclopropylethyl 3-cyclopropylpropanoate
17. ethanamine 18. ethanoic anhydride
19. ethyl ethanoate 20. methyl propanoate
21. hexan-3-amine 22. 5-bromooctan-2-amine

1. 2-phenylnonanedioic acid 2.7-sulfo-3-(trifluoromethyl)non-8-ynoic acid
3. 6-hydroxy non-8-enoic acid 4. 6-chloro-2-mercaptohexane-3-sulfonic acid

5. 6-cyclohexyl-5-hydroxy-6-methoxyhexanoic acid
6. 6-amino-3-hydroxy-2-methyl-7-sulfodec-9-enoic acid
7. 6-amino-3,5-dimethyl-4-(1-methylethyl)oct-7-ynoic acid
8. 6,7-dichloro-8-nitro-3-sulfodec-9-enoic acid 9. 5-(ethoxycarbonyl)-2-methylhexanoic acid
10. 5,5-dimethyl-4-oxohexanoic acid 11. 4-(Phenoxycarbonyl)butanoic acid

12. 3,7-dihydroxy-6-methylheptanoic acid
13. 2-ethenyl-5-mercepto-6-methyloct-7-enoic acid

14. 8-methyl-4-nitro-6-sulfodeca-2,9-dienoic acid
15. 2-bromo-6-chloro-3-ethynyl-4-hydroxy-7-methoxyoct-7-enoic acid

1. 2,4-diamino-5-methylhexan-3-ol 2.3-amino-7-hydroxy-2-methyloctanedioic acid
3. 3-(chlorocarbonyl)-4-cyanopentanoic acid 4. 6-carbamoyl-5-formyloct-3-enoic acid
5. 4-bromo-5-(ethoxycarbonyl)-3-ethylheptanoic acid
6. 5-(acetyl amino)-4-(trichloromethyl)heptanoic acid
7. 6-carbamoyl-5-(chlorocarbonyl)nona-4,7-dienoic acid
8. 4-sulfohexanoic acid 9. 3-cyano-4-ethylhex-4-ene-2-sulfonic acid
10. 2-(1-ethoxycarbonylpropyl)non-8-enoic acid 11. 2-cyano-4-propyloct-5-enoyl chloride
12. 2-oxopropanal 13. 5,10-dioxodec-6-ene-3-sulfonic acid

14. cyclohexanecarboxylic acid 15. cyclohexanecarbaldehyde

1. cyclohexanecarbonyl chloride 2. 2-methylbutanenitrite
3. ethyl cyclohexanecarboxylate 4. methyl cyclohexanecarboxylate
5. ethyl cyclopropanecarboxylate 6. methyl cyclopropanecarboxylate

7. cyclopropanecarbonyl chloride 8. cyclopropanecarbaldehyde
9. cyclopentanecarboxylic acid 10. cyclopentanecarbonyl chloride
11. cyclopentanecarbonitrile
1. 5-(chlorocarbonyl)-3-cyanohepta-2,4-dienoic acid 2. 3-(ethoxycarbonyl)but-3-enoic acid
3. 3-hydroxy-2-(methoxycarbonyl)hex-4-enoic acid
4. ethyl-5-chlorocarbonyl-2-(3-hydroxybutyl)pent-2-enoate
5. 2-oxopropanal 6. 2-oxopropanoyl chloride

7. 2-[1-(N-methylamino)propyl]hex-2-enamide 8. 3-amino-4-hydroxy-5-merceptohexanoic acid

1. 3,5-dibromohexan-2-amine 2. 4-methylhex-5-yn-2-amine
3. 6-methyloct-7-en-2-amine 4. 2-cyclopropylheptan-4-amine
5. 6-bromo-5-chloro-3-methylhept-1-en-4-amine 6. 2-cyclobutylnon-8-yn-3-amine
7. 1-cyclohexylpropan-2-amine

1. ethanoic anhydride 2. butanoic ethanoic anhydride
3. ethanoic propanoic anhydride 4. ethanoic propanoic anhydride
5. 3-bromobutanoic ethanoic anhydride 6. 2-bromoethanoic 2-chloropropanoic anhydride
7. heptanoic pentanoic anhydride 8. ethanoic pentanoic anhydride
9. ethenyl ethanoate 10. but-3-enoic pentanoic anhydride
11. but-3-enoic ethanoic anhydride 12. but-3-ynoic hexanoic anhydride
13. but-3-enoic but-3-ynoic anhydride

1. 2-bromo-N-chloroethanamide 2. N-bromo-2-chloro ethanamide
3. N-propylbutanamide 4. ethanamide
5. N-but-2-enylpent-2-enamide 6. 3-cyclopropylbut-3-enamide
7. N-(2-bromopropyl)-3-chloropentanamide 8. N-butylethanamide
9. N-penta-1,3-dienylbut-3-ynamide 10. cyclohexanecarboxylic ethonoic anhydride
11. cyclobutylethanoic cyclohexanecarboxylic anhydride
12. hepta-3,5-dien-1-amine
13. hexa-1,4-dien-3-amine 14. 3-bromo-7-cyclobutylnon-5-en-4-amine

1. 4-amino-2-methylpentanoic acid 2. 2-amino-3-chloro-2-methylbutanoic acid
3. 2-methyl-5-sulfohexanoic acid 4. 2-cyclopropyl-2,7-dimethyl-6-sulfo non-8-enoic acid
5. 7-aminooctane-2-sulfonic acid 6. 6-methylheptan-2-amine
7. 8-cyclohexyl-4-methyl-9-oxonon-2-enoic acid 8. 2,6dimethyl-7-oxo octanoyl chloride
9. 2,4-dimethyl-5-oxopentanoyl chloride 10. 2,3-dimethyl-4-oxobutanoyl chloride

11. 6-methoxy-6-methyloct-7-ene-2-sulfonic acid 12. 5-cyclopropyl-6-oxoheptane-2-sulfonic acid
13. 1,4-dimethyl-5-oxopentyl ethanoate 14. 5-amino-7,7,7-trichloro-2, 6-dimethylheptanoic acid
1. 2-carbamoylpentane-3- sulphonic acid 2. methyl 2-ethyl-6-methyl-7-oxoheptanoate
3. 6-cyclohexyl-3-methylheptan-2-one 4. ethyl-4-amino-4-cyclohexyl-2-methyl butanoate
5. 3-amino-2-methyl-7-sulfo octanoic acid 6. 6-ethyl 1-methyl 3-amino-2,5-dimethylhexanedioate
7. ethyl 4-cyano-3-methoxy-2-methylbutanoate 8. phenyl-5-(N-ethylamino)-2-methylhexanoate
9. 5-ethenyl-4,4-diphenylhept-5-enoic acid 10. 4-amino-6,6,6-trifluoro-4-methylhexan-3-one
11. 2,4-dimethyl-3-(1-methylethyl)pentane-3-sulfonic acid
12. N-(2-methylbut-3-yn-1-yl)acetamide

1. 4(1-ethenylprop-1-enoxycarbonyl) pentane-1-sulfonic acid
2. 5-ethoxycarbonylhexanoic acid
3. 4-methoxycarbonylbutanoic acid 4. 3-pentoxycarbonylpropanoic acid
5. 4-cyano-2-cyclopropylbutane-1-sulfonic acid 6. 3-(N,N-dipropylamino)-2-methylhexanoic acid
7. ethyl 3-aminobutanoate 8. prop-2-ynoic acid
9. ethyl 5-(chlorocarbonyl)-6,6,6-trifluoro-4-methylhexanoate
10. ethyl 2-amino-3-chloro-4-cyclohexylhex-5-enoate
11. 3-ethynyldec-9-enoic acid
12. 4-(chlorocarbonyl)undec-1-en-10-yne-3-sulfonic acid
13. 6,6-dichloro-5-sulfo nonanoic acid
14. 7-(chlorocarbonyl)-3-methyldeca-1,9-diene-4-sulfonic acid
15. 9-carbamoyl-7-methylnona-1,8-diyne-1-sulfonic acid
16. 2,4-dimethyl-3-(1-methylethyl)pentane
17. 6-bromo-4-chloro-6-cyclopropyl-5-nitrohexanal

1. propylbenzene 2. butyl benzene 3. 1-phenyl ethene 4. phenyl ethyne
5. 1-phenyl ethene 6. benzene 7. 1-phenyl hex-1-ene
8. 1-phenyl but-1-yne

1. benzenecarboxylic acid or benzoic acid 2. benzenecarbonyl chloride or benzoyl chloride
3. benzenecarboamide or benzamide 4. ethyl benzene carboxylate or ethyl benzoate
5. methyl benzene carboxylate or methyl benzoate
6. benzenecarbonitrile 7. 2-cyano benzenecarboxylic acid or 2-cyanobenzoic acid

1. (3-methylbutyl)benzene 2. 1-phenylethanone
3. 1-methylpropylbenzene 4. 2-bromo-4-chloro-1-ethylbenzene
5. 1-phenylpent-2-en-1-one 6. N-(2-hydroxyphenyl)but-2-enamide
7. benzenesulfonic acid 8. 3-methoxyphenol
9. 2-chloro-5-methoxybenzoic acid 10. methoxybenzene
1. benzene-1,2-diol2. benzene-1,2-diol3. benzene-1,2-diol 4. 3-chlorophenol
5. 2-bromophenol 6. 5-bromo-2-chlorophenol
7. 2-formyl-5-hydroxy benzene carbonitrile or 2-formyl-5-hydroxybenzonitrile

8. 5-bromo-2-hydroxy benzene carbonitrile or 5-bromo-2-hydroxybenzonitrile
9. methyl 2-cyano benzene carboxylate or methyl 2-cyanobenzoate
10. nitrobenzene 11. 1-bromo-2-chloro-4-nitrobenzene

1. 1,2-dibromo-4-nitrobenzene 2. 1-bromo-2-chloro-4-nitrobenzene
3. 2-bromo-1-chloro-4-nitrobenzene 4. 2-bromo-5-chlorophenol
5. toulene or methylbenzene 6. 2,4-dibromo aniline 7. 5-bromo-2-chloro aniline

1. 1-phenylbutane-1,3-dione 2. 1,2-diphenylethanone
3. diphenylmethanol 4. diphenylmethanone
5. (trichloromethyl)benzene or 1,1,1 trichloro-1-phenyl methane 6. 1,2-dichlorobenzene
7. 1,2,4-trichlorobenzene 8. 1-bromo-2,4-dichlorobenzene
9. 2-bromo-1,4-dichlorobenzene 10. 1-bromo-4-chlorobenzene

1. 2-(methoxycarbonyl)benzenecarboxylic acid 2. 2-carbamoyl benzenecarboxylic acid
3. cyclopropylbenzene 4. cyclopropylbenzene
5. ethyl methyl benzene-1,2-dicarboxylate 6. benzene carbaldehyde or benzaldehyde
7. 1-phenylethanone 8. 2-cyclopropyl-1-phenylethanone

1. 4-chloro-3-hydroxybenzaldehyde 2. 2,2-dimethyl-1-phenylpropan-1-one
3. 1-methylethylbenzene 4. (3-hydroxyphenyl)(phenyl)methanone
5. 4-chloro-3-nitrobenzonitrile 6. 2-amino-5-bromophenol
7. tetraphenylmethane 8. benzene-1,2-dicarboxylic acid
1. 2-bromo-6-hydroxybenzonitrile 2. 3-(ethoxycarbonyl)benzoic acid

3. 2-acetylbenzoic acid 4. ethyl 2-(chlorocarbonyl)benzoate
5. 2-formyl-5-hydroxybenzamide 6. 2-chloro-5-cyanobenzamide
7. diphenylmethanone 8. 1-phenylcyclopenta-2,4-dien-1-ol

1. benzene-1,2-dicarboxylic acid 2. benzene-1,2-dicarbaldehyde
3. 3,4-dichlorophenol 4. 2-methylaniline
5. trifluorophenylmethane 6. 3-nitrobenzonitrile
7. methyl 2-formylbenzoate 8. N-phenylbenzamide

1. N-phenylmethanamide 2. N-phenylbutanamide
3. N-(3-bromophenyl)methanamide 4. phenyl propanoate
5. N-phenylaniline
6. N-(2-bromo-6-chlorophenyl)-2-phenylethanamide
7. N-(5-bromo-2-chlorophenyl)-2-cyclopropylethanamide
Answer Key of DPP No- 47
1. –I 2. –I 3. –I 4. –I 5. –I
6. +I 7. +I 8. –I 9. –I 10. –I
11. –I 12. +I 13. –I 14. –I 15. –I
16. No effect 17. –I
1.
(a) –I (b) –I (c) +I (d) –I (e) –I (f) –I
(g) –I (h) +I (i) +I (j) –I (k) +I (l) –I
(m) +I (n) –I (o) –I (p) –I (q) –I (r) None
(s) +I (t) None
1. +I 2. +I 3. +I 4. –I 5. –I 6. –I 7. –I
8. +I 9. None 10. –I 11. –I 12. –I 13. –I 14. –I
15. –I 16. –I 17. –I 18. +I 19. –I 20. –I 21. +I
22. +I 23. +I 24. –I 25. –I 26. –I 27. –I 28. –I
29. –I 30. –I 31. None 32. –I 33. +I 34. +I 35. +I
36. +I 37. None 38. +I 39. +I 40. –I 41. –I 42. +I
43. +I 44. –I 45. –I

1. i > ii 2. i > ii 3. i > ii 4. ii > i 5. i > ii 6. i > ii 7. i > ii
8. i > ii 9. i > ii 10. i > ii 11. ii > i 12. i > ii 13. i > ii 14. i > ii
15. ii > i 16. i > ii
1. 2. 3. 4.

CH2
5. 6. 7.    8.

CH3
9. 10. 11.
H2C
12. 13. 14.
15. 16. 17. 18.
19. 20. 21.
H
H + H
N
+ +
+ +
22. 23. 24. No d-orbital in nitrogen ,

+ + +
Resonance in
benzene only
25. 26. 27.

28. 29. 30.
31.


NH2

O
1. 2. 3.  
  CH3–C

O

  
NH2  
 
4. 5. 6.
O
    


OCH3
 O
 
7. 8. C 9.
  O O


Cl

O
  
10. 11.  12.
 
NH2


OCH3
    
13. 14. 15.

  

O

O
 
O   OH
16. 17. 18.
O O


   
 
 
1. 2. 3. 4.
  
  
 
–
O
 
     
5. 6. 7.

O–

 H
O 

 –
N
8.  O 9. 10. 
  
 
OH S O
 
11. 12. 13.  14.
 

OH


1.  2. 3. 
 OH 
 O
 
NH2 O
    
O
4. 5. 6. 

 

O
 
CH — CH — NH2

O
 


7. NH 8. 9.
 
 
O H
1 1
2 O O 2
1
O 2

10.   11. 12. H
H2N O
 
1 1 1
O 2
2 O O 2
•  
CH2
 
13. 14. 15. Me — S — CH 2
• •  

CH2
  
O
  
16. Me N 17. 18. H 2N — C — N:

 
O N
 
O O

O
    Me
19. N 20. O — C — O or O—C—O 21.  
  O  N:
O O
  
H2N NH2 O
C
22. 23. 24.
NH     
OH
 

    15
O O 
 15  15
25. 26.   27.  or 
 15 15
  

O

O
  
  O

28. 29. 30. C O
 
   O
O

1. I > II 2. II > I 3. I > III > II 4. I > II > III 5. I > II > III > IV
6. I > III > II > IV 7. I > II 8. I > II > III

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COMPLETE COURSE IN ORGANIC CHEMISTRY

BY VINEET KHATRI SIR

(A) Methyl 2-ethylbutanoate (B) 1-methoxy-2-ethylbutanone

(A) But-1-en-4-oic acid (B) 1-hydroxybut-2-en-1-one

(A) 1-Methoxy-1-methylpropene (B) 2-Methoxybut-2-ene

(A) Ethyl 2-methylprop-2-enoate (B) Ethyl 2-methylprop-1-enoate

(A) 2, 3-Dimethylbutan-4-amine (B) 2, 4-Dimethylbutan-1-amine

(A) 3-(Methylethyl)pentan-2-one (B) 3-(Methylethyl)pentan-4-one

(A) 2-Methylbutanoyl bromide (B) 2-Methylbutan-4-oyl bromide

(A) 2-Phenylpropan-1-ol (B) 2-Phenylpropan-3-ol

(A) 3-lodo-4, 5, 5-trimethylhexane (B) 4-lodo-1, 1, 3-trimethylhexane

(A) 4-Chloro-2, 3-dimethylhexane-2-ol (B) 4-Chloro-2-hydroxy-2, 3-dimethylhexane

(A) 2-Methylbutan-3-one (B) 3-Methylbutan-2-al

(A) Ethanoic propanoic anhydride (B) Propanoic ethanoic anhydride

(A) Butane-2, 3-dial (B) Butane-1, 3-dione

5. CH2 — CH2 –– CH2

(A) Pentane-1, 5-dioic acid (B) Pentane-1, 5-dicarboxylic acid

(A) Tris(chloromethyl) methane (B) 1, 3-Dichloro-2-(chloromethyl) propane

(A) 3, 5, 5-Trimethylhexane-2, 4-diol (B) 2, 2, 4-Trimethylhexane-3, 5-diol

(A) 1-formyl-1-methoxyethane (B) 2-Methoxypropan-3-one

(A) Methyl-2-methylprop-1-en-3-oate (B) 2-Methoxycarbonylpropene

(A) But-2-ene-1-oic acid (B) But-1-ene-1-oic acid

(A) 2,2-Dimethyl-4-chloro butane (B) 1-Chloro-3, 3-dimthylbutane

13. CH3 — CH — CH — CH — CH3

(A) 3-Bromo-4-chlorpentan-2-ol (B) 3-Bromo-2-chloro-4-hydroxypentane

15. CH3 — CH — CH2 — O — C2H5

(A) 1-Ethoxypropan-2-ol (B) 3-Ethoxypropan-2-ol

(A) 2, 6-Dimethylhepta-2, 5-dienoic acid (B) 3, 7-Dimethylhepta-2, 5-dienoic acid

(A) 3-Methylpent-1-en-4-al (B) 3-Methylpent-4-enal

4. Give the IUPAC name of the following compounds :

5. Write the structure of the following organic halogen compounds.

(iii) CH3 – CH – CH – CH3 (iv) HOCH2 – CHOH – CH2OH

7. Write structures of the compounds whose IUPAC names are as follows :

1. Name the following compounds according to IUPAC system of nomenclature :

2. Draw the structures of the following compounds :

1. Write the IUPAC name of the following compound: [CBSE-: 2004]

CH2 — CO — CH2 — CH2 — CH2 — Cl

3. Write the IUPAC name of the compound: [CBSE-: 2007]

4. Name the following compound according to IUPAC system: [CBSE-: 2007abroad]

5. Write the IUPAC name of the following compound: [CBSE-: 2008]

H3C — CH — CH2 — CH — CH — CH2OH

6. Give the IUPAC name of the following compound: [CBSE-: 2009]

7. Write the structure of 3-oxopentanal. [CBSE-: 2009]

9. Draw the structural formula of 1-phenylpropan-1-one molecule. [CBSE-: 2010]

11. Draw the structure of 4-chloropentan-2-one. [CBSE-: 2011]

BY VINEET KHATRI SIR

12. H3C CH3

13. H2C CH3

14. H3C CH3

19. H3C CH3

BY VINEET KHATRI SIR

BY VINEET KHATRI SIR

BY VINEET KHATRI SIR

BY VINEET KHATRI SIR

S.No. Compounds Write IUPAC - Name

BY VINEET KHATRI SIR

S.No. Compounds Write IUPAC - Name

BY VINEET KHATRI SIR

S.No. Compounds Write IUPAC - Name

BY VINEET KHATRI SIR

S.No. Compounds Write IUPAC - Name

12. H3C NH2

13. H3C CH2