Ms Chouhan & Team: Organic Chemistry

ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN.
DPP-85
S.N. Compound Huckel Rule (4n + 2)e– All carbon of ring Cyclic Complete delocalisation Nature
are sp2 or sp
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
Note : Huckel Rule (4n + 2)e– is for aromatic compound only.
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ANSWER KEY
1. 6 , , , Aromatic
2. 6 , , , Aromatic
3. 6 , , , Aromatic
4. × ×, , ×, Non-Aromatic
7. × , , , Anti-Aromatic
8. 6 , , , Aromatic
9. × × , ×, Not- Aromatic
10. × × , ×, Non- Aromatic

ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN. DPP-86
S.N. Compound Huckel Rule (4n + 2)e– All carbon of ring Cyclic Complete delocalisation Nature
are sp2 or sp
1.
2.
3.
4.
5.
6.
7.
N
|
H
8.
N O
|
H
9.
N
10.
Note : Huckel Rule (4n + 2)e– is for aromatic compound only.

ANSWER KEY
1. ×, ×, , ×, Non - Aromatic 2. 6 , , , Aromatic
3. ×, ×, , ×, Non - Aromatic 4. 6 , , , Aromatic
5. × , , , Anti-Aromatic 6. × ×, , ×, Non-Aromatic
7. 6 , , , Aromatic 8. 6 , , , Aromatic
9. 6 , , , Aromatic 10. × , , , Anti-Aromatic

Q. Identify the Nature of compound
S.No. Compound Aromatic Anti-aromatic Non-aromatic
(1)

(2)

(3)
+
(4)
+

(5)

(6)
(7)
O
(8)
(9)
(10)
(11)
B
|
H
(12)
O  O
(13)
O O
B
|
H

ANSWER KEY
Aromatic : Aro, Antiaromatic : A.A. Non-aromatic : N.A.
1. NA 2. AA 3. Aro 4. Aro 5. Aro
6. NA 7. NA 8. NA 9. Aro 10. AA
11. AA 12. Aro 13. Aro

(1)
(2)
O
(3)
S
(4)
N
|
H
(5)
O
(6)
O
(7)
O
(8)
(9)
(10)
(11)
O
O

ANSWER KEY
1. AA 2. Aro 3. Aro 4. Aro 5. NA
6. Aro 7. NA 8. NA 9. Aro 10. NA
11. Aro

(1)
O
(2)
N O
|
H
(3)
N
H
(4)
N
N
(5)
N
(6)
N
H
(7)

N
H
N N—H
(8)
(9) H—N N—H

ANSWER KEY
1. Aro 2. Aro 3. Aro 4. Aro 5. Aro
6. NA 7. Aro 8. Aro 9. Aro

Q. Identify the Nature of compound

1.
2.
3.
CH3
|
B
4.
5.

N
6.
N
|
H
7. N :S:
8. N
O
N N
9. N N
H N

ANSWER KEY
1. Aro 2. AA 3. Aro 4. Aro 5. Aro
6. NA 7. Aro 8. Aro 9. Aro

1.
2.
3.
4.
5.

CH2
6.

CH2
7.
8.
N
9.

ANSWER KEY
1. Aro 2. Aro 3. Aro 4. Aro 5. Aro
6. Aro 7. Aro 8. AA 9. Aro

1.
2.
3.
H
N
4.
CH2
5.
6. 
7.
8.
9.

ANSWER KEY
1. Aro 2. NA 3. Aro 4. Aro 5. Aro
6. AA 7. AA 8. Aro 9. Aro

1.
Using the information in figure, calculate the values of H° for the following reactions :
(a) (b)
(c)
2. Classify each as aromatic or antiaromatic or non-aromatic :
(a) (b) (c)
(d) (e) (f) [20] annulene dication
3. The following hydro carbon has an unusually high large dipole moment, explain why

4. Classify each as aromatic or antiaromatic or non-aromatic :
5. Explain why each compound is aromatic or antiaromatic or non-aromatic
(a) (b) (c) (d)
(e) (f) (g)
6. Which ion in each of the following pairs is more stable ?
(a) or (b) or (c) or \

+ – + – –
+
7. The following molecules and ions are grouped by similar structures. Classify each as aromatic, antiaromatic,
or nonaromatic. For the aromatic and antiaromatic species, give the number of pi electrons in the ring.
(a) (b)
(c) (d)
O
(e) (f)
–
H
(g) (h)

ANSWER KEY
1. (a) + 32 kJ/mol (b) – 88 kJ/mol (c) – 112 kJ/mol 2. (a) A.A (b) A (c) A
(d) A.A (e) N.A (f) A

3. Net dipole moment 4. A.A ; A ; A.A
(Zwitter ion)
5. (a) (b) (c) N.A (Csp3 present) (d) (e)
(f) N.A. (Csp3 present) (g)

6. (a) (i) > (ii) (b) (i) > (ii) (c) (ii) > (i)
7. (a) (i) N.A (ii) A.A, (iii) (b) (i) (ii) (iii) N.A. (iv) (v) NA,
(c) (i) N.A. (ii) (iii) A.A, (iv) A.A, (d) (i) (ii)
(iii) N.A. (iv) (e) (i) N.A. (ii) (iii)
(f) (i) (ii) (iii) N.A, 4es– (g) (i) (ii)
(iii) (h) (i) N.A. (ii) (iii) (iv)

1. The following hydrocarbon reacts with two equivalents of butyllithium to form a dianion of formula [C8H6]2–.
Propose a structure for this dianion, and suggest why it forms so readily.
+ 2C4H9Li  [C8H6]2– (Li+)2 + 2C4H10
2. How would you convert the following compounds to aromatic compounds ?
(a) (b) (c)
(d) (e) (f)
3. Is either of the following ions aromatic ?
+
–
(a) (b)
Cyclononatetraenyl
cation Cyclononatetraenide
anion
4. Which of the following compounds are aromatic ? Are any antiaromatic ? (Hint : If possible, a ring will be
nonplanar to avoid being antiaromatic.)
+CH
2
N +
+
–CH
2
N+
N O
H
H
H
N N N
N
N
N N O N H N
H H

5. Evaluate each of the following processes applied to cyclooctatetraene, and decide whether the species
formed is aromatic or not.
(a) Addition of one more  electron, to give C8H8–
(b) Addition of two more  electrons, to give C8H82–
(c) Removal of one  electron, to give C8H8+
(d) Removal of two  electrons, to give C8H82+
6. Evaluate each of the following processes applied to cyclononatetraene, and decide whether the species
formed is aromatic or not :
(a) Addition of one more  electron, to give C9H10–
(b) Addition of two more  electrons, to give C9H102–
(c) Loss of H+ from the sp3-hybridized carbon
(d) Loss of H+ from one of the sp2-hybridized carbons Cyclononatetraene

ANSWER KEY
1. (both rings are aromatic)
2. (a) Na or NaH (b) H2SO4 (c) AlCl3 or SbCl5 or Ag+NO3– (d) NaOH (e) Na or NaH (f) AlCl3
3. (a) Anti-aromatic (b) Aromatic
4. (i) Anti-aromatic (ii) Aromatic (iii) Non-aromatic (iv) Aromatic (v) Non-aromatic (vi) Aromatic
(vii) Anti-aromatic (viii) Aromatic (ix) Aromatic (x) Aromatic (xi) Non-aromatic
(xii) Aromatic (xiii) Aromatic (xiv) Anti-aromatic (xv) Anti-aromatic (xvi) Anti-aromatic
5. (a) Not Aromatic (b) Aromatic (c) Not Aromatic (d) Aromatic
6. (a) Non-Aromatic (b) Non-Aromatic (c) Aromatic (d) Non-Aromatic

RESONANCE ENERGY DPP
1. In each of the following pairs, which species is more stable ?
O OO OO
– –
(a) CH3CH2O– or CH3CO¯ (b) CH3CCHCH2CH or CH3CCHCCH3
O O NH
– –
(c) CH3CHCH2CCH3 or CH3CH2CHCCH3 (d) or CH3CNH2
O O
CH2
– N¯ or
(e) or CH3C – CH (f) N¯
CH3
O
2. Compare Resonance energy between the given compounds:

CH3 CH3 CH3 CH3
+ -
CH CH
+ -
H2C CH CH2 H2C CH CH2
(a) (b) (c) (d)
-
OH O
CH
H2C CH CH2
(e) (f) (g)
(h) (i)
Calix[5]arene Naphthacene
Perylene
Calix[4]arene
NO 2
- - -
- O OC O O2N O
H3C COO -
COO
NO 2
(j) Acetate Succinate (k)
Phenolate Picrate

O
-
O
- - O S O -
COO O O S
- -
O O
(l) Benzoate (m)

Phenolate Sulfate Sulfite
(n) (o) Naphthacene

Fluoranthene Aceanthrylene Chrysene
(p) (q) s-Indacene

Triphenylene Pyrene as-Indacene
O O
O
O
(r) (s)
Chroman 2H-Chromene
Benzofuran Isobenzofuran
S O
NH O
S C C
S
H2 N NH2 H2 N NH2
(t) (u)
Thianthrene Phenoxathiin Guanidine Urea
- -
O O O O
O S O O S O O S O S O
- -
O O O O
(v) Acenaphthylene Fluorene (w)

Peroxodisulfate Disulfate
O
O O
- -
O P O -
O P OH HO P OH
-
O - -
O O
3- 2- -
PO 4 HPO4 H2PO4
(x)
Phosphate Hydrogen phosphate Dihydrogen phosphate

O O
CH 2
(a) (b) (c) (d)
(e) (f)
H H
O N O O S
N
(g) (h) (i) (j)
NH2
H H H
+ -
CH CH B B B
(k) (l) (m) (n)

B
H
H H
B B H2C
H2C
H2C CH2
(o) (p) CH2
O N
H
CH2
CH2 H3C
HN
CH2
H2C HN
(q) CH3
H2 C H2 C
(r) H2C CH2
CH2
+ -
S CH CH
S
(s) H2C CH2 CH2 (t)
-
CH -
- CH
H2C -
H2C CH2 CH2
(u) (v)
- -
(w) H2C CH2 H2C CH2 (x) H2C
CH2
(y) H2 C CH2

(a) (b)
(c) Anthracene (d) N

Phenanthrene N H
(e) (f)
O O O O +
CH
+
CH
(g) OH NH2
(h) OH
-
O
(i)
O O NH2 OH OH OH
(j) NH2 NH
(k) OH NH2
(l)
+
- CH2
NH CH +
CH2
(m) (n)
O O O O O
(o) (p) HO H HO OH H H
+ +
+ +
OH OH
-
CH2
(q) CH2
- (r) (s)
F Cl F Cl
PH NH O O
(t) - - (u) -
PH NH OH NH

ANSWER KEY
1. (a) (ii) > (i) (b) (ii) > (i) (c) (ii) > (i) (d) (ii) > (i) (e) (i) > (ii) (f) (i) > (ii)
CH3 CH3
+ -
CH CH
+ -
H2C CH CH2 CH CH2
2. (a) < (b) > H2C (c) <
-
CH3 CH3 OH O
CH
H2C CH CH2
(d) > (e) < (f) >
(g) >
(h) < (i) <
Naphthacene
Perylene
Calix[5]arene
Calix[4]arene
NO 2
- - - -
(j) H3C COO < O OC (k) O < O2N O
-
COO
NO 2
Acetate
Succinate Phenolate Picrate
O O
- - -
(l) COO > O (m) O- S O > O S
- -
O O
Benzoate Phenolate Sulfite

Sulfate
(n) > (o) > Naphthacene

Fluoranthene Aceanthrylene Chrysene
(p) > (q) <
as-Indacene s-Indacene
Triphenylene Pyrene

O O
(r) >
Benzofuran Isobenzofuran
O O S O
(s) < (t) <
S S
Chroman 2H-Chromene
Thianthrene Phenoxathiin
NH O
C
(u) H2N < C (v) =
NH2 H2 N NH 2
Guanidine Urea Acenaphthylene Fluorene

- -
O O O O
(w) O S O O S O <O S O S O
- -
O O O O
Peroxodisulfate Disulfate
O O
O
-
- - O P OH HO P OH
(x) O P O > >
- -
- O O
O
2- -
HPO4 H2PO4
3-
PO 4 Dihydrogen phosphate
Hydrogen phosphate
Phosphate
O O
CH2
3. (a) > (b) < (c) > (d) <
(e) > (f) >
49 Kcal/mol 36Kcal/mol
H H
O N O O S
N
(g) < (h) < (i) > (j) <
NH2
H H H
+ -
CH CH B B B
(k) < (l) < (m) < (n) >

B
H
H H
B B H2C
H2C
H2C CH2
(o) < (p) < CH2
O N
H

CH2
CH2 H3C
HN
CH2
H2C HN
(q) CH3 < H2 C H2 C
(r) H2C CH2 <
CH2
+ -
S CH CH
S
(s) H2C CH2 < CH2 (t) >
-
CH -
- CH
H2C -
CH2 CH2
(u) < H2C (v) >
- -
(w) H2C CH2 < H2C CH2 (x) > H2C
CH2
(y) < H2 C CH2
4. (a) > (b) <
(c) < (d) > N

N H
Anthracene
Phenanthrene
(e) < (f) <
O O O O +
CH
+
CH
(g) OH
< NH2
(h) OH
< O
- (i) <
O OH OH
O OH
NH2
(j) NH2
< (k) = (l) <
NH OH NH2
+
- CH2
NH CH +
CH2
(m) < (n) <
O O
O O O
(o) < (p) > >
HO HO HO H H H

+ +
+ +
OH OH
-
CH2
(q) -
CH2
> (r) > (s) <
F Cl F Cl
PH NH O O
(t) - > - (u) < -

PH NH OH NH



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ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN.

Note : Huckel Rule (4n + 2)e– is for aromatic compound only.

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10. × × , ×, Non- Aromatic

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Note : Huckel Rule (4n + 2)e– is for aromatic compound only.

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S.No. Compound Aromatic Anti-aromatic Non-aromatic

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(9) H—N N—H

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Q. Identify the Nature of compound

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S.No. Compound Aromatic Anti-aromatic Non-aromatic

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2. Classify each as aromatic or antiaromatic or non-aromatic :

(a) (b) (c)

(d) (e) (f) [20] annulene dication

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5. Explain why each compound is aromatic or antiaromatic or non-aromatic

(a) (b) (c) (d)

(e) (f) (g)

6. Which ion in each of the following pairs is more stable ?

(a) or (b) or (c) or \

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5. (a) (b) (c) N.A (Csp3 present) (d) (e)

(f) N.A. (Csp3 present) (g)

(iii) N.A. (iv) (e) (i) N.A. (ii) (iii)

(f) (i) (ii) (iii) N.A, 4es– (g) (i) (ii)

(iii) (h) (i) N.A. (ii) (iii) (iv)

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