SRI CHAITANYA NARAYANA IIT ACADEMY

ORGANIC CHEMISTRY

M t

IIT JEE 2019

HYDROCARBON
e

GOC-(A)

PREPARED BY: ASHISH SIR & NEHA MADAM

SYNOPSIS

GOC

EXERCISE-A

One or more correct :

1. Which of the following resonating structure is most stable?

(A) CH3 – O – CH = CH – CH2 (B) CH3 – O – CH – CH = CH2

(C) CH3 – O = CH – CH = CH2 (D) CH3 – O – CH – CH – CH2

2. Shown below are three representations of protonated N, N–dimethylacetamide. Identify the incorrect

statement(s) –

OH
O
O OH OH CH3

CH3 H CH3 CH3 CH3 N

CH3 CH3 N
H 3C N H 3C N CH3 N

CH3 CH3 CH3 H

CH3 (I) CH3 (II) (III) (IV)

(A) Structure (IV) is not a resonance form of the other.

(B) Structure at the N–atom is predicted to be trigonal planar.

(C) Structure (III) is the least important of the resonance structures shown.

(D) The C – O Bond in protonated N, N–dimethyl acetamide would be shorter than the C–O bond in

N,N-dimethyl acetamide.

3. Find the correct statement(s) regarding inductive effrect?

(A) Polarisation of -bond caused by the polarization of adjacent -bond is referred as inductive effect.

(B) This effect is not passed on to the subsequenct bonds.

(C) During I–effect, e -does not leave the original orbital.

(D) This effect increases rapidly as the number of intervening bonds increases.

4. Which of the following statement(s) is (are) correct?

(A) In positive electromeric effect, – e of multiple bonds are transferred to that atom to which the reagent

gets attached.

(B) In negative electromeric effect, – e of multiple bond are transferred to that atom to which the reagent

gets attached.

(C) When inductive and electrometic effect operate in opposite directions, the electromeric effect predominates.

(D) Electromeric effect is annulled as attacking reagent is removed from the domain of the reaction.

5. Which of the following statement is correct about cycloctatetraene?

(A) It is non conjugated system. (B) If has "Tub" like conformation.

(C) It is a cyclic planar compound. (D) Chemically, it behaves like an alkene, not like benzene.

6. Which of the following cation is(are) not resonance stabilized?

 

(A) Vinyl cation ; CH 2  C H (B) Allyl cation ; CH 2  CH  CH 2

CH2

(C) Phenyl cation ; (D) Benzyl cation ;

7. Which of the following pairs are resonance structures of each other?

(A) (B)

(C) (D)

8. Which of the following is not aromatic compound?

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

9. In which of the following molecules, nitro group is not coplanar with phenyl ring?

H3C CH3

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

I I

N N O
N N
O O O O O

10. In given molecule, – e density is more on –

3 O

2 1

(A) 1 & 3 (B) 2 & 4 (C) 2 & 3 (D) 1 & 4

11. Among these compounds, the correct order of resonance energy is :-

CH 3COOH CH 3COONa CH 3COONH 2

I  II   III 

(A) I > II > III (B) III > II > I (C) II > III > I (D) II > I > III

12. There are three canonical structures of naphthalene, Examine them and find correct statement among the

following :-

1 1 1

2 2 2

3 3 3

4 4 4

(A) All C – C bonds are of same length.

(B) C1 – C2 bond is shorter than C2 – C3 bond

(C) C1 – C2 bond is longer than C2 – C3 bond

(D) None

13. Among these compounds, the correct order of C – N bond length is :-

NH2 NH2 NH2

CH2 = NH

(IV)
CHO (II) (III)

(I)

(A) IV > I > II > III (B) III > I > II > IV (C) III > II > I > IV (D) III > I > IV > II

14. The increasing order of stability of the following free radicals is :-

(A) (C6H5)3C < (C6H5)2CH < (CH3)3C < (CH3)CH

(B) (C6H5)2CH < (C6H5)3C < (CH3)3C < (CH3)2CH

(C) (CH3)2CH < (CH3)3C < (C6H5)3C < (C6H5)2CH

(D) (CH3)2CH < (CH3)3C < (C6H5)2CH < (C6H5)3C

15. Arrange the carbanions, in order of their decreasing stability –

(A) (CH3)2CH > CCl3 > C6H5CH2 > (CH)3C (B)

(C) (CH3)3C > (CH3)2CH > C6H5CH2 > CCl3 (D) C6H5CH2 > CCl3 > (CH3)2CH > (CH3)2C

16. For 1-methoxy-1,3-butadiene, which of the following structure is the least stable?

 

(A) CH 2  CH  CH  CH  O  CH 3
 
(B) CH 2  CH  CH  CH  O  CH 3

   
(C) CH 2  CH  CH  CH  O  CH 3 (D) CH 2  CH  CH  CH  O  CH 3

17. In which of the following case, resonance contribute LEAST toward stabilisation :-

H H H H
O=C–C=O O–C=C–O

(A) H O H O (B)

H H H H
H H H H

O O

(C) CH3 C CH3 C (D) CH3 – CH2 – O – CH2 CH3 – CH2 – O = CH2

NH2 NH2

18. The correct orientation of dipoles in pyrrole and pyridine is :-

(A) (B)

N N N N

H |

(C) (D)

N N N N

| |

H H

19. Assuming that each resonance structure contributes equally to the final resonance hybrid of phenanthrene,

Identify the longest bond and shortest bond in phenanthrene.

E
C

(A) A shortest & B longest (B) C shortest D longest

(C) E shortest & A longest (D) B shortest & C longest

20. Molecule with the highest dipole moment among the following is :-

O O

O O

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

Ph Ph Ph Ph Ph Ph

21. Among these cononical structure, the correct order of stability is :-

O O O

C C C

H OH H OH H OH

(I) (II) (III)

(A) I > II > III (B) III > II > I (C) I > III > II (D) II > I > III

22. Among these canonical structures, the least stable is :-

 

(I) CH 2  CH  CH  CH  OCH 3 (II) CH 2  CH  CH  CH  O CH 3

   

(III) CH 2  CH  CH  CH  OCH 3 (IV) CH 2  CH  CH  CH  OCH 3

(A) I (B) II (C) III (D) IV

23. Among these 3 canonical structures (through more are possible) what would be their contribution in the

"HYBRID"?

 

(I) CH3 – O – CH = CH – CH = CH2 (II) CH 3  O  CH  CH  CH  CH2

 

(III) CH 3  O  CH  CH  CH  CH2

(A) I > II > III (B) III > II > I (C) I > III > II (D) III > I > II

24. The most stable resonating structure of following compound is :-

O=N N=O

ao to y

(A) O = N N=O (B) O = N N–O

of

(C) O = N I N=O (D) O – N so N=O

I 1

25.
N N N N N

(I) (II) (III) (IV) (V)

Among these canonical structures of pyridine, the correct stability order is :-

(A) (I = V) > (II = IV) > III (B) (II = IV) > (I = IV) > III

(C) (I = V) > III > (II = IV) (D) III > (II = IV) > (I = V)

26.

Among these canonical structures of "Pyrrole".

The correct stability order is :-

(A) (III = IV) > (II = V) > I (B) I > (II = V) > (III = IV)

(C) I > (III = IV) > (II = V) (D) (II = V) > (III = V) > I

O O O

27.

N N N
| | |

H H H

(I) (II) (III)

The least stable canonical structrue among these –

(A) I (B) II (C) III (D) All are equally stable

28. In which of the following pairs, first species is more stable than second?

(A) CH3CH2O and CH3 – C – O

O O O O

(B) CH3 – C – CH – CH2 – CH and CH3 – C – CH – C – CH3

O O

c
(C) CH3CH – CH2 – C – CH3 and CH3CH2CH – C – CH3

O O

N and N
(D)

29. N = N , The most stable canonical structure of this molecule is :-

(A) N=N (B) N=N (C) N N (D) All are equally stable

SRI CHAITANYA NARAYANA IIT ACADEMY

ORGANIC CHEMISTRY

M t

IIT JEE 2019

HYDROCARBON
e

GOC-(B)

PREPARED BY: ASHISH SIR & NEHA MADAM

EXERCISE-B

1. The species that are aromatic among the following is(are) :-

H
| CH2

H O
N

(P) (Q) (R) (S)

(A) R (B) P (C) Q (D) S

2. The compound is

(A) Aromatic and has high dipole moment. (B) Aromatic and has no dipole moment

(C) non-aromatic and has high dipole moment (D) Anti-aromatic and has no dipole-moment

3. The compound that is "NOT AROMATIC" is :-

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

4. Cycloocta tetraene appears to be a conjugated annulene. In addition to the planar configuration, three non

planar structures may be considered, all of which are shown below, which of these is most likely to be the

favoured conformation.

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

5. Which of the following statement is are true for AZULLENE :

(AZULENE)

(A) Azulene is an ionic compound

(B) By charge transfer from Biggerring to smaller ring

(C) Azulene is non benzenoid system

(D) Azulene has greater dipole moment

6. Organic compounds sometimes adjust their electronic as well as steric structures to attain stability. Among the

following, the compound having highest dipole moment is :

Br

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

Br

Br Br

7. cyclooctatetraene is :

(A) Aromatic because it is planar and follow Huckle's rule

(B) Anti aromatic because it is not planar and it does not follow Huckle's rule

(C) antiaromatic because it is planar and it does not follow Huckel's Rule

(D) Non aromatic because it is not planar and it does not follow Huckel's rule

8. Which of the following compound is “NOT AROMATIC”.

O – O

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

O O O

O O

9.

(I) (II) (III)

The barrier for rotation about the indicated bonds will be maximum in which of these three compounds

(A) I (B) II (C) III (D) Same in all three

10. Which of the following reactions give aromatic compound ?

HBr
(A) KH (B)

HBr
Ph3CBr
HI

(C) (D)

AgClO 4

11. Cl (P)

, ClO4
– +
(A) + (B) – , Ag (C) mixture of (A) & (B) (D) None

12. The products P and Q in the following reaction respectively are

CH 3

Reaction-1 :
NaNH2
(P)

Cl

Reaction-2 : AgNO3
Cl (Q)

–
CH2
Cl –
CH2 +

(A) , (B) ,

+ Cl
(P) CH2

(Q) (P) (Q)

–
CH3 –
CH3 Cl

(C) , (D) ,
Cl +

(P) (Q) (P) (Q) CH2

13. How many of the following compounds can form “AROMATIC” product on the given reactions ?

CH3

(A) H2 (1 eq.) (B) + HBr

Metal catalyst

CH3

(C) + HClO4 (D) + AgNO3

O

Cl

14. Protonation of a carbonylgroup form a cation with significant charge on carbon atom which of the following

carbonyl compounds form an aromatic cation on protonation ?

O O O

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

KH

15. (P)

BuLi

(P) will be :

–
(A) + (B)

(C) mixture of (A) & (B) (D) None

16. Which one of the following statement(s) is(are) true :

(1) (2)

– +

(A) PhLi react readily with both compound

– +
(B) PhLi does not react to either of the compound

– +

(C) PhLi react readily with (1) but does not react to (2)

– +
(D) PhLi react readily with (2) but does not react to (1)

17. Correct order of rate of hydrolysis or rate of reaction toward AgNO3 aq for given compounds-

Br Br

Br
Br

(III) (IV)

(I)

(II)

(A) III > II > IV > I (B) I > II > III > IV (C) III > I > II > IV (D) III > II > I > IV

Cl
2 SbCl5
18. [P]

Cl

Product [P] will be -

–
(A) 2– (B) 2+ .2SbCl6 (C) (D) mixture of (A) & (B)

19. In the case of dibromo derivatives of the following compound, the derivative having highest energy has the

bromo substituents in positions

3 1
10

4
9

6 7
8

(A) 1, 2 (B) 2, 3 (C) 4, 5 (D) 1, 10

20. Which of the following compounds is/are aromatic ?

N
(A) BH (B) BH (C) NH (D)

21. The correct order of resonance energy (in KJ/mol) of the following aromatic compounds is :

N O

(I) (II) (III)

(A) I > II > III (B) II > I > III (C) III > II > I (D) II > III > I

22. The aromatic systems among the following are :

(I) (II) (III)

(IV)

(A) III and IV (B) I and II (C) II and IV (D) I and IV

23. The order of basicities of the following substituted anilines is -

NH2 NH2 NH2 NH2

O2N NO2

O2N NO2 NO2

(I)

CH3 (III) CH3

(II) (IV)

(A) I > II > III > IV (B) IV > I > III > II (C) IV > II > I > III (D) IV > III > I > II

24. The basicities (pKb) of the following series of compounds (I - IV),

NH2 NH2 NH2 NH2

NH2 NO2 OCH3

(I) (II) (III) (IV)

will vary as :

(A) IV > II > I > III (B) III > I > IV > II (C) I > II > III > IV (D) IV > III > II > I

SRI
ok CHAITANYA NARAYANA IIT ACADEMY

ORGANIC CHEMISTRY

IIT JEE 2019

HYDROCARBON

GOC-(C)

PREPARED BY: ASHISH SIR & NEHA MADAM

EXERCISE-C

Integer Type :

1. For the given structure [M] find the total number of Resonating structure (Uncharged).

[M]

2. Find the total number of Benzenoid rings present in all possible resonating structures of anthracene -

Anthracene

3. How many of the following structure s will have high contribution of ionic or polarized structures in their

resonance hybrid

O O
O

, , ,

NH2

4. M = number of Resonance structures contributed in Resonance hybrid of

NH3

N = number of Resonance structures contributed in Resonance hybrid of

Find the sum of (M + N) ?

5. Use the following data to answer the question below

H2

Ni

( H = –28.6 kcal/mol)

excess H2

Ni

Anthracene ( H = –116.2 kcal/mol)

Calculate the resonance energy of anthracene in kcal / mole :

6. Among the following the number of molecules that are aromatic as they are drawn -

, , ,

H Me

N , ,

Me

7. Among the following how many are aromatic compound(s) -

O O

, NH , , ,

N O B N S

H H CH3

8. How many of the given reactions product can be aromatic ?

2K 2C 4H 9Li
(i) (K) (ii) (L)

Cl

AgNO3
(M) 2K
(N)
(iii) (iv)

EtOK (O)

KH
Cl (P)

Cl

Ag
+
SbCl5

(v) (Q) (vi) (R)

Cl

Cl
SbCl5 SbCl5

(vii) (S) (viii) (T)

EXERCISE-D

1. The abstraction of proton will be fastest in which carbon in the following compound -

(y)
O
(x) (w)

H3C CH3
(z)

(A) X (B) Y (C) Z (D) W

2. Consider the acidity of the carboxylic acids -

PhCOOH , o–NO2C6H4COOH , p-NO2C6H4COOH , m-NO2C6H4COOH

(P) (Q) (R) (S)

which of the following order is correct

(A) P > Q > R > S (B) Q > S > R > P

(C) Q > S > P > R (D) Q > R > S > P

3. Find the correct acidic strength order -

H3C H3C

CH3CH2OH , CHOH , H3C C–OH

H3C H3C
(K) (L) (M)

(A) K > L > M (B) M > L > K (C) K > M > L (D) M > K > L

4. Which order of acidic strength is correct for given structures -

OH OH OH OH OH OH

NO2 CH3

, , , , , , EtOH

NO2 CH3
(K) (Q)

(L) NO2 (N) (O) (P)

(M)

(A) M > K > L > N (B) N > P > O > Q

(C) L > N P > O (D) M > K P > Q

M p

5. Consider the acidic strength of given structures

CF3COOH , CI3COOH , CHl2COOH, CH2ClCOOH, FCH2COOH , BrCH2COOH, NO2CH2COOH,

NC–CH 2 COOH, HCOOH, Cl.CH 2 CH 2 COOH, C 6 H 5 COOH, C 6 H 5 CH 2 COOH, CH 3 COOH,

CH3CH2COOH

Find the correct order of acidic strength -

(A) CCl3COOH > CHCl2COOH > NO2CH2COOH > NC-CH2COOH

(B) NO2CH2COOH > F.CH2COOH > Cl.CH2COOH > HCOOH

(C) HCOOH > C6H5COOH > C6H5CH2COOH > CH3COOH

(D) CF3COOH > NO2.CH2COOH > NC.CH2COOH > CHCl2COOH

O O
6. CH2=CH–C CH3–CH2–C

OH OH

(I) (II)

Find the correct statement(s) -

(A) pKa = I > II (B) pKa = II > I (C) Ka = I > II (D) Ka = II > I

OH OH OH OH

Me

7. , , ,

Me
(K) (L) Me

(M)

(N)

Acidic strength order -

(A) K > M > N > L (B) N > L > M > K (C) K > N > L > M (D) M > L > N > K

Cl

8. Me.CH2CH2.COOH MeCH2–CH–COOH

(P) (Q)

Cl Cl

CH2–CH2–CH2–COOH Me–CH–CH2–COOH

(R) (S)

Correct acidic strength is -

(A) Q > S > R > P (B) S > Q > R > P (C) P > Q > R > S (D) Q > P > S > R

9. O2N–CH2COOH Me–C–CH2COOH Me3N–CH2COOH

(1) (2) (3)

Correct acidic strength order is -

(A) 1 > 3 > 2 (B) 3 > 1 > 2 (C) 1 > 2 > 3 (D) 3 > 2 > 1

10. Me3N–CH2COOH N C–CH2COOH MeO–CH2COOH

(1) (2) (3)

Correct acidic strength order is -

(A) 1 > 2 > 3 (B) 2 > 1 > 3 (C) 2 > 3 > 1 (D) 1 > 3 > 2

11. MeO–CH2COOH HO–CH2COOH EtO–C–CH2COOH

(1) (2) (3)

Correct acidic strength order is -

(A) 1 > 2 > 3 (B) 3 > 1 > 2 (C) 3 > 2 > 1 (D) 2 > 3 > 1

COOH

12. HOOC COOH HOOC

(Cis)-butendioic acid (Trans)-butendioic acid

Find the correct statement(s)-

(A) pKa1 = Cis >Trans (B) pKa1 = Trans > cis

(C) pKa2 = cis > Trans (D) pKa2 = Trans > cis

COOH COOH COOH

13. , ,

Me

(1) (2) Me

(3)

Correct acidic strength order is -

(A) 1 > 2 > 3 (B) 3 > 2 > 1 (C) 2 > 3 > 1 (D) 1 > 2 > 3

COOH COOH COOH COOH COOH

NO2
14. , , , ,

NO2 O2N NO2

(1) (2) (3) NO2

(5)

(4)

Correct acidic strength order is -

(A) 2 > 5 > 4 > 3 > 1 (B) 2 > 5 > 3 > 4 > 1

(C) 5 > 2 > 4 > 3 > 1 (D) 5 > 2 > 3 > 4 > 1

COOH
COOH COOH COOH COOH

Cl Br OMe OH

,
15. , , ,

(1) (2) (3) (4) (5)

Arrange them in decreasing order of acidic strength -

(A) –Br > –Cl > –OH > –OMe > –H (B) –OH > –OMe > –Cl > –Br > –H

(C) –Br > –Cl > –OMe > –OH > –H (D) –OMe > –OH > –Br > –Cl > –H

COOH COOH COOH

Cl

16. , ,

Cl
(1) (2) Cl

(3)

Correct order of acidic strength -

(A) 1 > 2 > 3 (B) 1 > 3 > 2 (C) 3 > 1 > 2 (D) 3 > 2 > 1

COOH COOH COOH,

Br

17. , ,

Br

(1) (2) Br

(3)

Correct order of acidic strength -

(A) 1 > 2 > 3 (B) 1 > 3 > 2 (C) 3 > 1 > 2 (D) 2 > 1 > 3

18. Compare acidic strength

COOH COOH COOH

OH OMe HO OH

, ,

(1) (2) (3)

(A) 3 > 1 > 2 (B) 3 > 2 > 1 (C) 1 > 3 > 2 (D) 1 > 2 > 3

19. Consider the given dicarboxylic acid -

COOH COOH

COOH COOH

COOH , HCOOH , CH3COOH , ,

(1) (2) (3)

(4) (5)

(A) 1 > 5 > 2 > 4 > 3 (B) 1 > 5 > 4 > 2 > 3

(C) 5 > 1 > 4 > 2 > 3 (D) 5 > 1 > 2 > 4 > 3

20. Which of the following is most acidic -

H H H H
H H H H

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

21. Which is the correct method for separating a mixture of benzoic acid p-methyl aniline and phenol

(A) NaHCO 3 aq. NaOH (B) aq. HCl aq. NaHCO3

(C) aq. NaOH aq. NaHCO3 (D) aq. NaOH aq. HCl

22. The structural formula for vitamin C is shown below out of the four hydroxyl group identified by circles

which is most acidic

(A) 1 (B) 2 (C) 3 (D) 4

23. The most acidic isomer hydrocarbon among the following is.-

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

CH3 CH2 CH3 CH3

23. Among the following given compounds

O O O O

OH OH OH OH

I II III IV

The decreasing order of their acidity is :

(A) I > II > III> IV (B) II > I > IV > III (C) III > IV > I > II (D) IV > III > II > I

24. A chemist wishes to separate benzoic acid from 4-hydroxybenzaldehyde. Which is the best method to

achieve this separation ?

COOH CHO

HO
benzoic acid

4-hydroxybenzaldehyde

(A) Partitioninig the mixture between diethyl ether and water

(B) Partitioning the mixture between diethyl ether and 1 M aqueous NaHCO3

(C) Partititoning the mixture beween diethyl ether and 1 M aqueous NaOH

(D) Partititoning the mixture beween diethyl ether and 1 M aqueous HCl

25. The correct order of acidity for the following compounds is -

COOH COOH COOH COOH

HO OH OH

, , ,

OH

(I) (II) (III) OH

(IV)

(A) I > II > III > IV (B) III > I > II > IV (C) III > IV > II > I (D) I > III > II > IV

26. Arrange the following compounds in order of decreasing acidity -

OH OH OH OH

Cl CH3 NO2 OCH3

(I) (II) (III) (IV)

(A) II > IV > I > III (B) I > II > III > IV (C) III > I > II > IV (D) IV > III > I > II

27. The correct acidity order of the following is -

OH OH OH OH

Cl CH3 NO2 OCH3

(I) (II) (III) (IV)

(A) III > IV > II > I (B) IV > III > I > II (C) III > II > I > IV (D) II > III > IV > I

28. When benzene sulphonic acid and p nitrophenol are treated with NaHCO3 the gases evalve respectively are

(A) SO2, NO2 (B) SO2, NO (C) SO2, CO2 (D) CO2, CO2

29. Which of the following is obtained when 4 methylbenzene sulphonic acid is hydrolysed with excess of

sodium acetate -

(A) H3C COONa (B) H3C + SO3

(C) H3C SO3Na + CH3COOH (D) H3C SO2OCOCH3 + NaOH

30. Arrange in order of increasing acidic strength -

+ +
H3N NH3

(z) (y)

COOH

(x)

(A) X > Z > Y (B) Z < X < Y (C) X > Y > Z (D) Z > X > Y

HOOC OH
3 2

31. 2 moles of NaNH2

O2N
C CH

4
OH

Proton will be removed from -

(A) 1 (B) 2 (C) 3 (D) 4

32. which of the following has the most acidic hydrogen is

(A) 3 Hexanone (B) 2,4 hexanedione (C) 2,5 hexandione (D) 2,3 hexanedione

33. Among the following find the correct acidic strength order

CH CH C6H6 C2H6 CH3OH

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

(A) 1 > 4 > 2 > 3 (B) 4 > 1 > 3 > 2 (C) 4 > 1 > 2 > 3 (D) 1 > 4 > 3 > 2

Note : Answer the Q no 34, 35,36 by appropriately matching the information given in the three columns of the

following table

Column-I Column-II Column-III

(pKa)

SO3H

(1) (P) 16 (K) Give effervescence with NaHCO3

COOH

(2) (Q) 15.3 (L) React with NaOH

(3) (R) –65 (M) More acidic than water

(4) CH3OH (S) 4.2 (N) Gives H2 gas on reaction with Na metal

34. Which option is correct

(A) 1-R-K (B) 2-Q-K (C) 3-S-L (D) 4-P-K

35. Which option is incorrect

(A) 1-R-M (B) 2-P-N (C) 3-P-N (D) 4-Q-M

36. Which of the following option is correct

(A) 1-Q-L (B) 2-R-M (C) 3-P-N (D) 4-Q-K

37. Arrange the following compounds in the increasing order of the acidity of circuled hydrogens

(I) (II) H

(III)

(A) III < II < I (B) II < I < III (C) I < II < III (D) II < III < I

38. The two compounds shown below, fumaric and maleic acid, are geometric (E/Z) isomers of each other.

Interestingly, maleic acid is more acidic with a pK a of 1.9 as compared to fumaric acid’s pKaof 3.0. This is

because.

O
OH O O

HO OH

HO
O

Maleic acid
Fumaric acid

(A) maleic acid has more strain and is thus more acidic

(B) Maleic acid has a larger molecular dipole and dissolves better in water

(C) the conjugate base of fumaric acid is better stabilized through the pi-orbitials

(D) the conjugate base of maleic acid has an intramolecular hydrogen bond

SRI CHAITANYA NARAYANA IIT ACADEMY

ORGANIC CHEMISTRY

M t

IIT JEE 2019

HYDROCARBON
e

GOC-(D)

PREPARED BY: ASHISH SIR & NEHA MADAM

EXERCISE-E

Integer Type :

1. Among the following the total number of compounds soluble in aq NaOH is

H3C CH3

N COOH NO2 OH OCH2CH3

CH2OH

H3C CH3

OH CH2CH3 COOH

CH2CH3

2. How many compounds are soluble in aqueous NaOH ?

O OH COOH OH
CH3

O OH

CH3

COOH OH OH
OH

HO OH O2N NO2

NO2 C N

3. How many of the following acids are more acidic than benzoic acid ?

COOH

O O O
OCH3

H H5C2 F3C
OH OH OH

COOH COOH COOH COOH

OH

CF3 CH3 OCH3

EXERCISE-F

One or More than Correct :

NOTE : Consider the basic strength of following given compounder and answer the Q No 1, 2, 3 & 4.

CH3NH2 , (CH3)2NH , (CH3)3N , C2H5NH2 , (C2H5)2NH ,

(1) (2) (3) (4) (5)

NH2 CH2NH2 NH–CH3

(C2H5)3N , , ,

(6) (7) (8) (9)

N(CH3)2

(10)

1. IdentifyAH
the correct basic strength order

(A) 5 > 6 > 2 > 4 > 3 > 1 (B) 8 > 10 > 9 > 7

(C) 2 > 1 > 3 > 8 > 7 (D) 5 > 6 > 4 > 10 > 9 > 7

2. Find the incorrect order -Of basic strength

(A) 10 > 9 > 7 > 8 (B) 2 > 4 > 1 > 3 (C) 2 > 5 > 7 (D) 8 > 9 > 10

3. Find the correct order -

(A) 5 > 2 (B) 4 > 1 (C) 6 > 3 (D) 8 > 10

4. Which of the following are homologous -

(A) 8,9, 10 (B) 2, 3 (C) 3, 6 (D) 2, 5

5. Arrange the following in decreasing order of basic strength order -

C6H5NH2 , C2H5NH2 , (C2H5)2NH , NH3

(P) (Q) (R) (S)

(A) Q > R > S > P (B) R > Q > S > P (C) R > Q > P > S (D) S > R > Q > P

6. Arrange the following in increasing order of their basic strength -

Aniline , p-nitroaniline , p-toluidine

(P) (Q) (R)

(A) R > P > Q (B) P > R > Q (C) Q > P > R (D) Q > R > P

7. Compare the basic strength of following -

NH2 NH2 NH2 NH2

Me

Me

Me (m) (o) (h)

(p)

(A) p > m > h > o (B) p > o > m > h (C) o > p > m > h (D) p > m > o > h

NH2 NH2 NH2 NH2

NO2

8.
NO2

(h) NO2 (m) (o)

(p)

Find the correct order of basic strength -

(A) h > m > p > o (B) h > p > o > m (C) h > o > m > p (D) h > o > p > m

9. Find the correct statements regarding the given compounds -

Me Me

NH2 N

O2N NO2 O2N NO2

(K) (L)

NO2 NO2

(A) pKb = K > L (B) pKb = K < L (C) Ka = K > L (D) Ka = K < L

NH2 NH2 NH2

OMe

10.

OMe

OMe (m) (o)

(p)

Correct order of Basic strength -

(A) p > o > m (B) p > m > o (C) o > p > m (D) o > m > p

NH2 NH2 NH2

OH

11.

OH

(m) (o)
OH

(p)

Correct order of Basic strength -

(A) p > o > m (B) p > m > o (C) o >? p > m (D) o > m > p

12. What is the decreasing order of strength of the base -

– – – –
OH , NH2 , H–C C , CH3–CH2

(P) (Q) (R) (S)

(A) S > Q > R > P (B) R > S > Q > P (C) P > Q > R > S (D) Q > R > P > S

13. The correct order of basicities of the following compound is -

O
NH

CH3–C CH3CH2NH2 (CH3)2NH CH3C–NH2

NH2 (Q) (R) (S)

(P)

(A) P > R > Q > S (B) P > Q > R > S (C) R > P > Q > S (D) R > Q > P > S

14. The correct order of basic strength of following amines is :

Me Me

N NH2 NH2 NH2

Me Me Ah
Me Me
dear

Me Me O2N NO2 O2N NO2

(I) (II) NO2 CN

(III) (IV)

(A) I > II > III > IV (B) I < II < III < IV (C) II < I > IV > III (D) I > II > IV > III

15. The reactivity of following compounds with proton will be in the order of -

N N N N N

H H H (IV) H

(I) (II) (III) (V)

(A) I > II > V > IV > III (B) II > I > V > IV > III

(C) I > II > IV > V > III (D) III > IV > V > II > I

16. The order of decreasing basicity of the following compounds is :

N N N N

H II III H
I IV

(A) II > III > I > IV (B) III > II > I > IV

(C) IV > I > II > III (D) IV > I > III > II

17. The least basic amine among the following is -

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

N N N N
H H H H

18. The increasing order of basicity of the following compouns is :

Me NH2

NH2 NH H2N NH H2N NH

(I) (II) (III) (IV)

(A) I < II < III < IV (B) I < II < IV < III (C) II < I < III < IV (D) IV < III < II < I

SRI CHAITANYA NARAYANA IIT ACADEMY

ORGANIC CHEMISTRY

M t

IIT JEE 2019

HYDROCARBON
e

GOC-(E)

PREPARED BY: ASHISH SIR & NEHA MADAM

EXERCISE - G

N N NH

NH NH
NH

A B C D E AB

Answer question 1-5 by selecting a SINGLE compound from SET - 1 abov e :

1. Select a SINGLE compound that has an sp2 N and is non - aromatic as drawn.

2. Select the SINGLE compound that when protonated on N has the lowest pKa.

3. Select a SINGLE compound that is anti - aromatic as drawn.

4. Select a SINGLE compound that is aromatic as drawn and has an aromatic conjugate acid .

5. Select a SINGLE compound that is non - aromatic as drawn but has an aromatic tautomer .

6. The electron - donating nature of the ethyl group accounts for the difference in base strength of ethylamine and

ammonia.

Which one of the following correctly shows the effect of the ethyl group ?

effect on strength of C2H5NH2 as a effect on strength of C2H5NH3+ as an

base relative to NH3 acid relative to NH4+

(A) increase increase

(B) increase decrease

(C) decrease decrease

(D) decrease increase

7. Which sequence gives the correct order of basic strength (strongest first) ?

most basic least basic

(A). C2H5NH2 NH3 (C2H5)2NH

C2H5NH2 (C2H5)2NH C6H5NH2

(B).

(C). (C2H5)2NH NH3 C6H5NH2

(D). C6H5NH2 NH3 C2H5NH2

8. Choose the weakest base :-


(A) Na S (B) Li

H H


(C) Na CC–CH3 (D) Na O

9. Choose the species that could not be used as the base in the following reaction :-

H + B C + BH

(A) (B) Na O
Li

(C) Na H (D) 

N Li

10. Which compound is most basic ?

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

N N N N
H H H

11. Which of (a) - (d) is not aromatic ?

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

N O + 

N N O N OH
H H H

H H

12. Which is least reactive towards an electrophile ?

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

N N N N

H
H

13. Which is most stabilized by electron delocalization (resonance) ?

(A) (B) (C) (D) 

O N N N
O

14. Which of (a) - (d) is not aromatic ?

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

N N N
B N

H H H

15. The correct order of the basicity of the following compounds is :-

N N N N

H H III H

I II IV

(A) IV > III > II > I (B) III > IV > I > II (C) IV > III > I > II (D) III > IV > II > I

16. Which of the following compounds form salt with NaHCO3 :-

H N CH3 COOCH3 COOH OH

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

17. The order in which the reagent must be used to seperate the compound I - III is -

OH COOH NH2

NO2 NO2 NO2

I II III

(A) NaOH, NaHCO3, HCl (B) HCl, NaOH, NaHCO3

(C) NaHCO3, NaOH, HCl (D) NaOH, HCl, NaHCO3

18. Which one of the following Lewis structure is not correct :-

:
O

: :

:
(A) :O O O

: :
(B)

: :

: :
 :O OH

:
H

: :

(C) N N (D) S

:
: :

: :
H : Cl Cl :

19. Draw the two most important additional contributing structures for the carbocation shown below :-

C H
O

H3C 1C 2

C3 ? ?

H H

Use your structures as a guide to determine which one of the following statements about this carbocation is

incorrect ?

(A) There is a significant build up of positive charge on the oxygen atom

(B) The Cl-O bond between the methoxy group and the allyl group has partial double bond character

(C) Except for the methyl hydrogen atoms, you would expect this cation to be planar.

(D) There is a significant build up to positive charge on C2 atom of the allyl group.

20. The value of ‘n’ for the following molecule according to Huckel’s rule is :-

(A) 16 (B) 4 (C) 3 (D) 14

21. Observe the following reaction :-

–
COOH O Na+ COONa OH

+ +

NO2 NO2

OH ONa

NO2 NO2

+ NaHCO3 + H2CO3

NO2 NO2

ONa OH

+ H2CO3 + NaHCO3

Which of the following is / are incorrect order of acid stregth :

OH OH COOH OH OH

NO2

(A) > H2CO3 > (B) > > > H2CO3

NO2 NO2

COOH OH OH OH COOH OH

(C) (D)
> H2CO3 > > > > > H2CO3

NO2 NO2

22. Which of the following statements are correct ?

COOH COOH

NO2

(A) > (Acidic strength)

NO2

(B) Et2 NH > Me2NH (Basic Strength)

(C) CF3COOH < NO2– CH2COOH (Acidic Strength)

(D) PhCH2NH2 > NH3 (Basic Strength)

23. Which of the following order of cation stability is correct ?

CH2

 
CH2=CH–CH2

, ,

(R)
(P) (Q)

(A) P > Q > R (B) Q > P > R (C) P > R > Q (D) Q > R > P

24. A solution of (+) –1–Chloro–1–phenyle thane in toluene racemise slowly in presence of small amount of sbCL5

due to formation of :-

(A) carbanion (B) free radical (C) carbene (D) carbocation

25. Compare the stability of the following free radicals :-

Ph3C Ph2CH PhCH2 CH2=CH– CH2 Me3C Me2CH MeCH3

, , , , , ,
(1) (2) (3) (4) (5) (6) (7)

(A) 1 > 2 > 3 (B) 3 > 4 > 5 (C) 5 > 3 (D) 4 > 3

26. Compare the stability of following free radicals :-

CH3–CH2 , CH2=CH , CHC

(1) (2) (3)

(A) 1 > 2 > 3 (B) 3 > 2 > 1 (C) 2 > 1 > 3 (D) 2 > 3 > 1

27. Compare the stability :-

, CH2=CH , CHC

(1) (2) (3)

(A) 1 > 2 > 3 (B) 2 > 1 > 3 (C) 3 > 2 > 1 (D) 2 > 3 > 1

28. Compare the bond energy of indicated C–H Bond :-

CH3–CH2 CH2–CH=CH–CH2 CH3

(a) (b) (c) (d) (e) (f)

(A) e > b > a > f (B) c = d

(C) c = d > f > a > b > e (D) e > b > a > f > c = d

29. Compare the stability of the following free Radical :-

(A) P > Q > R > S (B) R > P > Q > S

(C) R > Q > P > S (D) R > Q > S > P

30. Compare the Stability of following cations :-

   

Ph3C , Ph2CH , PhCH2 , Me3C

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

(A) 1 > 2 > 3 > 4 (B) 1 > 2 > 4 > 3

(C) 1 > 4 > 2 > 3 (D) 3 > 4 > 2 > 1

SRI CHAITANYA NARAYANA IIT ACADEMY

ORGANIC CHEMISTRY

M t

IIT JEE 2019

HYDROCARBON
e

GOC-(F)

PREPARED BY: ASHISH SIR & NEHA MADAM

EXERCISE - H

1. Identify the correct order of stability of given :-

  

(A) CH3CH2 > CH2= CH > CHC (B) CH2CF3 < CH2= CCl3 < CH3

  

(C) CH2–F > CH2–Cl > CH2–Br (D) CH2–NH2 > CH2–OH > CH2–CH3

2. Compare the stability of given cations :-







CH3–CH,2–CH2 , CH2=CH–CH2 , CH2–CH2

(1) (2)
(3)

(A) 1 > 2 > 3 (B) 2 > 1 > 3 (C) 3 > 2 > 1 (D) 2 > 3 > 1

3. Consider the following carbanions :-

Ph3C , Ph2CH , PhCH2 , CH2=CH–CH2 , CH
C , CH2=CH, CH3 , CH3CH2 , (CH3)2CH , (CH3)3C

(1) (2) (3) (4) (5) (6) (7) (8) (9) (10)

Identify how many stability order is (are) correct :-

(P) 4 > 3 (Q) 1 > 2 > 3 (R) 7 > 8 > 9 (S) 5 > 4

(T) 5 > 6 > 7

(A) P, Q, R, T (B) Q, R, S, T (C) Q, R, T (D) P, S

4. Identify the correct stability order :-

(A) CH2–CCL3 > CH2–CF3 (B) CCl3 > CF3

CH2 CH2 CH2

NO2 >  
>

>
(C) (D)

NO2

NO2

5. Identify the correct stability order :-

Me Me Me Me

CH2 , ,

Me
(1) (2) (3) Me

(A) 3 > 2 > 1 (B) 3 > 1 > 2 (C) 1 > 3 > 2 (D) 3 > 2 = 1

6. Which of the following compouds is not aromatic :-


O O

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

O O O

O O

7. Arrange in decreasing Ka :-

(a) F–CH2CH2COOH (b) Cl–CH–CH2–COOH

Cl

(c) F–CH2–COOH (d) Br–CH2–CH2–COOH

Correct answer is :

(A) b > d > a > c (B) a > c > d > b (C) c > b > a > d (D) d > b > a > c

8. Ease of ionization to produce carbocation and bromide ion under the treatment of Ag will be maximum in

which of the following compounds ?

(A) O Br (B) O Br

(C) (D)
N Br N Br

Ph CH3

9. (I) (II) (III)

O N

Which of the following choice is the correct order of resonance energy of these molecules :-

(A) I > II > III (B) II > I > III (C) III > II > I (D) III > I > II

10. Which of the following statements would be true about this compound :-

NO2

1 3

NO2 NO2

Br

(A) All three C – N bonds are of same length

(B) C1 – N and C3 – N bonds are of same length but shorter than C5 – N bond

(C) C1 – N and C3 – N bonds are of same length but longer than C5 – N bond

(D) C1 – N and C3 – N bonds are of different length but bot are longer than C5 – N bond.

NH2
NH2

11. NH2
:

N N
:

I II III IV

Which of the following statement/s is / are correct regarding above compounds ?

(A) I & II are aromatic and have equal basic strength

(B) I is aromatic, II is antiaromatic but II is stronger base than I

(C) Basic strength of the above compounds is I < II < III < IV

(D) Conjugate acid of IV is more stabilized than conjugate acid of II

12. The CORRECT order of stability of the following carbonium ions is :-

+ +
+

I II III

(A) II > I > III (B) III > II > I

(C) I > III > II (D) II > III > I

13. What is the increasing order of stability of following carbocations (give least stable first) ?

(I) Tropylium cation (II) CH2 = CH–CH2+ (III) (C6H5)2 C+ (IV) CH3+

(A) III < I < II < IV (B) IV < II < III < I

(C) I < III < II < IV (D) IV < III < II < I

14. Which one of the following is not aromatic ?

H H

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

15. The least basic amine among the following is :-

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

N N N N

H H H H

16. Arrange the following molecules in the increasing order of C-H bond dissociaton energy (kJ mol–1). :-

H
H
H

H H H3C CH3

(I) (II) (III) (IV)

(A) IV < II < III < I (B) I < III < IV < II

(C) III < II < IV < I (D) II < IV < I < III

17. The structure which is not a resonance structure of others in the following is :-

O O O O

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

18. Among the following the compound which would not be considered aromatic in its behavior is :-

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

N N
H

19. Answer the Following questions :-




S O O

N O

(A) (B) (C) (D) (E) (AB) (AE) (CD) (CE)

(i) An ionic molecule that is aromatic as drawn with 6 p-electrons.

(ii) A non-aromatic, uncharged heterocycle.

(iii) A hydrocarbon molecule that is non-aromatic as drawn, but reacts readily with H+ to give an aromatic

carbocation.

(iv) Not aromatic as drawn, but has an aromatic tautomer.

(v) Of the aromatic heterocycles, which would be the strongest base ?

SRI CHAITANYA NARAYANA IIT ACADEMY

ORGANIC CHEMISTRY

M t

IIT JEE 2019

HYDROCARBON
e

GOC-(G)

PREPARED BY: ASHISH SIR & NEHA MADAM

EXERCISE - I

1. Match the column :-

Column - I(Acids) Column - II(ka)

1. Benzoic acid (P) 4.2 × 10–5

–5

2. p-nitrobenzoic acid (Q) 3.3 × 10

–5

3. p-chlorobenzoic acid (R) 6.4 × 10

4. p-methylbenzoic acid (S) 36.2 × 10–5

–5
5. p-methoxybenzoic acid (T) 10.2 × 10

2. The number of resonance structures for N is :-

OH
NaOH

3. The total number of contributing structures showing hyperconjugation (involving C–H bonds) for the following

carbocation is

CH2CH3
H3C

4. Among the following, the number of aromatic compound (s) is

  

One or More Correct :

5. The IUPAC name (s) of the following compound is (are) :-

H3C Cl

(A) 1-chloro-4-methylbenzene (B) 4-chlorotoluene

(C) 4-methylchlorobenzene (D) 1-methyl-4-chlorobenzene

6. The compound that does NOT liberate CO2 , On treatment with aqueous sodium bicarbonate solution, is

(A) Benzoic acid (B) Benzenesulphonic acid

(C) Salicylic acid (D) Carbolic acid (Phenol)

7. The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to

(A)   p (empty) and   *electron delocalisations.

(B)   and    electron delocalisations.

(C)   p (filled) and   electron delocalisation.

(D) p (filled)  and  electron delocalisation.

8. The correct stability order for the following species is :-

  
O O 

(I) (II) (III) (IV)

(A) (II) > (IV) > (I) > (III) (B) (I) > (II) > (III) > (IV)

(C) (II) > (I) > (IV) > (III) (D) (I) > (III) > (II) > (IV)

9. Among the following the least stable resonance structure is :-


 O  O

(A) N (B)  N

O O

O  O

(C) N (D)  N r

O O

10. The correct acidity order of the following is :-

OH OH COOH COOH

I Cl III CH3

II IV

(A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II)

(C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I)

11. In the following carbocation, H/CH3 that is most likely to migrate to the positively charged carbon is :-

H H

1 2 + 4 5
H3C C C
3
C CH3

OH H CH3

(A) CH3 at C-4 (B) H at C-4 (C) CH3 at C-2 (D) H at C-2

12. The correct stability order of the following resonance structures is

+ – + – – + – +
H2C=N=N H2C–N=N H2C–N=N H2C–N=N

(I) (II) (III) (IV)

(A) I > II > IV > III (B) I > III > II > IV (C) II > I > III > IV (D) III > I > IV > II

13. The IUPAC name of the following compound is

OH

CN

Br

(A) 4-Bromo-3-cyanophenol (B) 2-Bromo-5-hydroxybenzonitrile

(C) 2-Cyano-4-hydroxybromobenzene (D) 6-Bromo-3-hydroxybenzonitrile

ANSWER KEY

EXERCISE-A

1. (C) 2. (D) 3. (A,C) 4. (A,C,D) 5. (A,B,D)

6. (A,C) 7. (A,C) 8. (D) 9. (C) 10. (B)

11. (C) 12. (B) 13. (C) 14. (D) 15. (B)

16. (C) 17. (B) 18. (A) 19. (A) 20. (C)

21. (C) 22. (D) 23. (C) 24. (D) 25. (A)

26. (C) 27. (B) 28. (D) 29. (C)

EXERCISE-B

1. (B,D) 2. (A) 3. (C) 4. (A) 5. (A,B,C,D)

6. (D) 7. (D) 8. (D) 9. (B) 10. (A,B,C)

11. (A) 12. (C) 13. (A,C) 14. (A,C,D) 15. (B)

16. (C) 17. (A) 18. (B) 19. (D) 20. (B)

21. (A) 22. (D) 23. (A) 24. (B)

EXERCISE-C

1. (10) 2. (6) 3. (3) 4. (7) 5. (84)

6. (3) 7. (3) 8. (9)

EXERCISE-D

1. (A) 2. (D) 3. (A) 4. (A,B,C,D) 5. (A,B,C)

6. (B,C) 7. (A) 8. (A) 9. (A) 10. (A)

11. (B) 12. (B,C) 13. (A) 14. (A) 15. (A)

16. (A) 17. (A) 18. (A) 19. (A) 20. (A)

21. (A,B) 22. (C) 23. (C) 23. (D) 24. (B)

25. (D) 26. (C) 27. DEL 28. (D) 29. (C)

30. (A) 31. (C,D) 32. (B) 33. (C) 34. (A)

35. (B) 36. (C) 37. (D) 38. (A &D)

EXERCISE-E

1. (4) 2. (7) 3. (5)

EXERCISE-F

1. (B,C,D) 2. (A,C,D) 3. (A,B,C,D) 4. (C,D) 5. (B)

6. (A) 7. (A) 8. (A) 9. (A,C) 10. (A)

11. (A) 12. (A) 13. (A) 14. (A) 15. (A)

16. (D) 17. (A) 18. (C)

EXERCISE - G

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

6. (B) 7. (C) 8. (A) 9. (B) 10. (C)

11. (C) 12. (B) 13. (C) 14. (D) 15. (C)

16. (C) 17. (C) 18. (C) 19. (D) 20. (C)

21. (B,D) 22. (A,B,D) 23. (A) 24. (D) 25. (A,D)

26. (A) 27. (B) 28. (B,C) 29. (C) 30. (B)

EXERCISE - H

1. (A,B,C,D) 2. (B) 3. (B) 4. (B,C) 5. (C)

6. (D) 7. (C) 8. (D) 9. (C) 10. (C)

11. (C,D) 12. (D) 13. (B) 14. (C) 15. (A)

16. (A) 17. (C) 18. (B) 19. (i)-CE ; (ii)-CD ; (iii)-A ; (iv)-E ; (v)-B

EXERCISE - I

1. (1)R ; (2)S ; (3)T ; (4)P ; (5)Q 2. (9) 3. (6)

4. (5) 5. (A,B) 6. (D) 7. (A) 8. (D)

9. (A) 10. (A) 11. (D) 12. (B) 13. (B)

Organic chemistry Previous years jee advanced questions

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