JEE (Main + Adv.

) Division

Daily Practice Problems

Chemistry

GENERAL ORGANIC
CHEMISTRY
(GOC)

Motion Corporate Office

Motion Education Pvt. Ltd., 394 - Rajeev Gandhi Nagar, Kota-5 (Raj.)

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 GENERAL ORGANIC CHEMISTRY
®
DPP-1
JEE [MAIN + ADV.] DIVISION
SINGLE CORRECT QUESTIONS

 
1. The inductive effects of the groups : – CH3,  CO 2 , – Br,  NH 3 are respectively
(A) + I –I +I –I (B) + I +I –I –I
(C) +I –I –I –I (D) – I +I –I +I

2. Select the correct order of positive inductive effect (+I.E.)

(A) –CMe3 > –CH2Me > – CHMe2 > –CH3 (B) –CH3 > –CH2Me > –CHMe2 > –CMe3
(C) –CMe3 > –CHMe2> –CH2Me > –CH3 (D) –CH3 > –CHMe2 > –CH2Me > –CMe3

3. The most powerful negative inductive effect (–I.E.) showing group among the following is:
 
(A)  NH 3 (B) –NO2 (C) –F (D)  N F3

4. Correct statement about inductive effect is :

(A) It is a temporary effect
(B) It decreases as the distance increases.
(C) It doesn't depend upon the electronegativity
(D) It operates through -bond only.
5. Which of the following groups has the highest + I effect ?
(A) CH3 — (B) CH3 CH2 — (C) (CH3)2 CH — (D) (CH3)3 C —

6. Maximum –I effect is exerted by the group

(A) C6H5 — (B) — OCH3 (C) —Cl (D) —NO2

7. Decreasing –I effect of given groups is :

(i) –CN (ii) – NO2 (iii) –NH2 (iv) –F
(A) iii > ii > i > iv (B) ii > iii > iv > i (C) iii > ii > iv > i (D) ii > i > iv > iii

8. Select correct statement about I effect?

(A) I effect transfers electrons from one carbon atom to another.
(B) I effect is the polarisation of  bond electrons.
(C) I effect creates net charge in the molecule.
(D) I effect is distance independent.
9. Which of the following group shows +I-effect :
(A) –Br (B) –COOH (C) –OR (D) –COO–
10. The inductive effect :
(A) Implies the atom’s ability to cause bond polarization
(B) Increases with increase of distance
(C) Implies the transfer of lone pair of electrons from more electronegative atom to the lesser
electronegative atom in a molecule
(D) Implies the transfer of lone pair of electrons from lesser electronegative atom to the more
electronegative atom in a molecule
11. In the following benzyl/allyl system
R – CH = CH2 or (R is alkyl group)
increasing order of inductive effect is –
(A) (CH3)3C–>(CH3)2CH–>CH3CH2— (B) (CH3CH2–>(CH3)2CH–>(CH3)3C—
(C) (CH3)2CH–>CH3CH2–>(CH3)3C— (D) (CH3)C–>CH3CH2–>(CH3)2CH—

Answer Key

1. B 2. C 3. D 4. B 5. D 6. D 7. D
8. B 9. D 10. A 11. A
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 GENERAL ORGANIC CHEMISTRY
®
DPP-2
JEE [MAIN + ADV.] DIVISION
SINGLE CORRECT QUESTION

1. During delocalization, which statement is incorrect :

(A) Net charge remains same
(B) Number of paired electrons remain same
(C) Number of unpaired electrons remain same
(D) Energy of resonating structures always remains same

2. Resonance structure of the molecule does not have

(A) higher energy than their hybrid structure.
(B) identical arrangement of atoms.
(C) the same number of paired electrons.
(D) always equal contribution to the resonance hybrid.

3. Which of the following species can not show resonance?

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

4. Resonance is not possible in :

(A) (B) (C) CH2 = CH — Cl (D)

5. Which does not have conjugate system ?

(A) CH2 = CHCl (B) CH2 = CHCHO (C) CH3CH = CH2 (D)

6. The compound which is not resonance stabilised

(A) CH2=CH–Cl (B) (C) CH2=CH–CH2Cl (D)

7. Which of the following is not acceptable as resonating structure :

(A) (B) (C) (D) None of these

8. Which of the following pair is not pair of resonating structures?


(A) & (B) & CH2 – CH  O

   
(C) CH2 = CH – O – CH3 & CH2 – CH  O– CH3 (D) CH3 – C  O & CH3 – C  O

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9. Which of the following structures are resonance structures ?

(A) & CH3–O–N=O (B) &

(C) (CH3)2CO & (D) CH3–CH=CH–CH3 & CH3–CH2–CH=CH2

10. Among the given sets, which represents the resonating structure ?

(A) and (B) and

(C) and (D) and

11. Stability order of the following species ?

(A) > >  (B) > >  (C) > >  (D) > > 

12. Which of the following is incorrect for stability of structures.

O¯ O¯
| |
(A) CH3  CH  CH  CH2 > CH3  C  CH  CH3

(B) <

(C) >


(D) CH2  CH  CH  CH  C H2 >

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

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

   –  
(C) CH3  O  CH CH CH2 (D) CH 3  O  CH  CH  CH 2
  
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14. Which of the following is most contributing resonating structure of prop-2-enal

–  
(A) CH2  CH  CH  O (B) CH 2  CH  CH  O


(C) CH2  CH  CH  O– (D) None of these

15. Which of the following are not valid resonating structures.

 
(A) (B)

O O O O


(C) (D)

N  N
 H H

Answer Key
1. D 2. D 3. A 4. A 5. C 6. C 7. B
8. A 9. B 10. B 11. B 12. A 13. D 14. D
15. B
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 GENERAL ORGANIC CHEMISTRY
®
DPP-3
JEE [MAIN + ADV.] DIVISION
SINGLE CORRECT QUESTION
1. The aromaticity of following heterocyclics

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

is in the order:
(A) 1 > 2 > 3 > 4 (B) 4 > 1 > 2 > 3 (C) 3 > 2 > 1 > 4 (D) 4 > 1 > 3 > 2

2. Select the one which does not results in the formation of aromatic species.
O
KH
(A)  (B) HBr



HI
O
(C)  (D) HBr



3. Which of the following heterocylic compounds would have aromatic character?

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

4. Which of the following species is having dimerization tendency?

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

5. is anti-psychotic drug is non planar to avoid being ............... ?

S
S
(A) Resonance Stabilisation (B) Anti Aromaticity
(C) Aromaticity (D) Non Aromaticity
6. Which of the following is an aromatic species.

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

7. Select aromatic compounds:

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

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

8. Select incorrect statement for

(A) 4 electrons are participating in resonance

(B) Compound is anti aromatic
(C) It is a Homocyclic compound
(D) Compound is non aromatic
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9. Which of the following is aromatic species?

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

10. Which of the following is anti-aromatic species?

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

11. Which of the following is non-aromatic?

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

12. Which of the following is non-aromatic?

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

13. Which is the most aromatic in character?

(A) (B)

(C) (D) All having same aromatic character

14. Which of the following is aromatic?

H
–
B
H
H–N N–H
(A) H (B) (C) (D)
H–B B–H
N
H

15. Select the correct statement about the following compounds.

(I) (II)
(A) II has a greater dipole moment than I (B) Covalent character of II is less than I
(C) I is more soluble in polar solvent than II (D) None of these

Answer Key
1. D 2. D 3. D 4. C 5. B 6. A 7. B
8. B 9. D 10. D 11. B 12. C 13. B 14. C
15. C
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 GENERAL ORGANIC CHEMISTRY
®
DPP-4
JEE [MAIN + ADV.] DIVISION
SINGLE CORRECT QUESTION
1. Which cation is most stable.

  
(A)  (B) (C) (D)

2. Which is more stable.

 
(I) CH 3  C  CH 3 (II) CD 3  C  CD3
| |
CH 3 CD3
(A) I > II (B) II > I (C) I = II (D) Stability can't be predicted

3. Correct order of stability of carbocation is:

 
 

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

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

4. Order of stability of following carbocation:

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

5. Most stable carbonium ion is

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

6. Write correct order of stability

(A) I > II > III > IV (B) III > II > I > IV
(C) III > I > II > IV (D) III > II > IV > I
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7. Which of the following is most stable :

(A) CH3 (B) CH2= CH (C) CH C (D) CH3–C C

8. Which one of the carbanions is most stable :

CH 2 CH2
CH2 CH2
(A) NO 2 (B) (C) CN (D)
NO2 CN

9. Most stable carbonium ion in the following will be:

(A) (B)  (C) (D) 

10. What is the decreasing order of strength of the bases,

OH , NH2 , , CH3–CH2
(I) (II) (III) (IV)
(A) IV > II > III > I (B) III > IV > II > I
(C) I > II > III > IV (D) II > III > I > IV

11. Arrange stability of the given carbocations in decreasing order :

   
CH2 CH2 CH2 CH2

OCH3 OH NH2 Cl

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

12. Which of the following statement is correct about arrow headed ‘C’ of

(A) Negative charge is delocalised due to sp2 hybridisation

(B) sp2 hybridised but (–)ve charge is localised
(C) sp3 hybridised and (–) ve charge is not delocalised.
(d) sp3 hybridised and (–) ve charge is delocalised.

13. Which has localized ve charge :

  
NH3 CH2 CH3 CH2

(a) (b) (c) (d) H2N–C=NH 2
NH2
(A) a, d (B) a, c (C) c, d (D) b, d

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14. Which is most stable carbocation :



(A) (B) C

(C) CH2=CH–CH 2 (D) 

15. Which is most stable carbocation :


(A) C (B) (C) (D)

Answer Key
1. C 2. A 3. C 4. A 5. C 6. B 7. C
8. A 9. C 10. A 11. B 12. B 13. B 14. A
15. C
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 GENERAL ORGANIC CHEMISTRY
®
DPP-5
JEE [MAIN + ADV.] DIVISION
SINGLE CORRECT QUESTION
1. Which of the following alkene is most stable alkene.
(A) CH3– CH2– CH = CH2 (B) CH3 – CH = CH – CH3
CH3 CH3 CH3 CH3
(C) C=C (D) C=C
H CH3 CH3 CH3

2. Which of the isomer of C4H8 is most stable.

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

3. Which of the following has maximum dipole moment?

Cl Cl Cl
Cl Cl
Cl
(A) (B) (C) (D)
Cl Cl Cl
4. Which of the following alkene does not contains 8  H.

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

5. In which of following I intermediate is less stable.

CH2

(A) CF3  H2C– & CH3  CH2– (B) &

CH2–
CH–2

(C) & (D) &

Cl Cl

6. Which free radical is the most stable :

(A) C 6H 5–CH 2 (B) CH2=CH–CH2 (C) CH3–CH–CH 3 (D) CH 3–C–CH 3

CH3

7. Increasing order of the stability is :

CH3CH=CH2 CH3CH2CH=CH2, (CH3)3CCH=CH2

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

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

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8. Give the decreasing order of hyperconjugative effect of R in R–CH = CH2, where R is :
I. Me– II. Et– III. Me2CH– IV. Me3C–
(A) I > II > III > IV (B) IV > III > II > I
(C) II > I > III > IV (D) IV > III > I > II

9. Which of the following molecules, in pure form, is (are) unstable at room temperature ?
O

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

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

   
(A) (C6H5)3 C <(C6H5)2 CH <(CH3)3 C <(CH3)2 CH
   
(B) (C6H5)2 CH <(C6H5)3 C <(CH3)3 C <(CH3)2 CH
   
(C) (CH3)2 CH <(CH3)3 C <(C6H5)3 C <(C6H5)2 CH
   
(D) (CH3)2 CH <(CH3)3 C <(C6H5)2 CH <(C6H5)3 C

11. Consider the following compounds

Hyperconjugation occurs in :
(A) II only (B) III only (C) I and III (D) I only

12. (I) (II) (III)

Compare carbon-carbon bond rotation across I, II, III.

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

13. Which of the following shows the correct order of decreasing stability :
   
(A) CH3 CH2 > CH3O CH2 > CH2 > CH 3–CH2

   
(B) CH3O CH2 > CH3 CH2 > CH2 > CH3 –CH 2

   
(C) CH2 > CH3O CH2 > CH3 CH2 > CH –CH
3 2

   

(D) CH3O CH2 > CH2 > CH –CH
3
> CH3 CH2
2

14. Arrange the carbanions, , , , , in order of their decreasing stability

y:

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

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

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15. The total number of contributing structures showing hyperconjugation (involving C—H bonds)
for the following carbocation is :

(A) three (B) five (C) eight (D) six

Answer Key
1. D 2. D 3. C 4. D 5. B 6. A 7. A
8. A 9. B 10. D 11. B 12. C 13. B 14. B
15. D

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 GENERAL ORGANIC CHEMISTRY
®
DPP-6
JEE [MAIN + ADV.] DIVISION
SINGLE CORRECT QUESTION
1. Which is most acidic out of following?
(A) Ph–OH (B) HCOOH (C) MeOH (D) H2O

2. Correct decreasing order of acidic strength is:

(I) CH3COOH (II) CH3COOOH (III) PhOH (IV) H2SO4
(A) I > IV > III > II (B) IV > I > III > II
(C) I > IV > II > III (D) II > IV > I > III

3. Arrange in increasing order of acidic strength.

COOH OH OH COOH
O2N NO2 NO2 OH NO2

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

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

4. Which one of the following is the strongest base in aqueous solution ?

(A) Trimethylamine (B) Aniline
(C) Dimethylamine (D) Methylamine

5. Which of the following substituents will decrease the acidity of phenol :

(A) –NO2 (B) –CN (C) –CH3 (D) –CHO

6. Which of the following substituted carboxylic acids has the highest Ka value :

(A) (B) CH3–CH–CH2–COOH

Cl

(C) CH 2–CH 2–CH2–COOH (D) CH3–CH–CH2–COOH

Cl Br

7. Which is most acidic compound :

COOH COOH
COOH COOH
CH3
(A) (B) (C) (D)
CH3
CH3

8. Which of the following shows the correct order of decreasing acidity :

(A) PhCO2H > PhSO3H > PhCH2OH > PhOH
(B) PhSO3H > PhOH > PhCO2H > PhCH2OH
(C) PhCO2H >PhOH > PhCH2OH > PhSO3H

(D) PhSO3H > PhCO2H > PhOH > PhCH2OH

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9. Which one of the following is the most acidic ?

(A) (B) (C) (D) CH2=CH–CH3

10. Arrange the following compounds in decreasing order of acidity ?

Cl

Cl
(I) C6H5–OH (II) (III) (IV)

OH
OH
Select the correct answer from the codes given below :
(A) III > II > IV > I (B) III > II > I > IV
(C) II > III > I > IV (D) II > III > IV > I
11. Which of the following is weakest acid ?
COOH
COOH

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

OH
12. Arrange acidity of given compounds in decreasing order :
(I) CH3–NH–CH2–CH2–OH (II) CH3–NH–CH2–CH2–CH2–OH

(III) CH3 3 N– CH 2 – CH 2 – OH
(A) III > I > II (B) III > II > I (C) I > II > III (D) II > I > III

13. Which is correct

OH OH OH
NO2
(A) R–NH2 > R–OH (pKa) (B) > > (Acidic strength)

NO2

COOH OH
CH3
(C) > (Ka) (D) All

SO3H
14. The correct order of increasing acid strength of the compounds :

(a) CH3CO2H (b) MeOCH2CO2H (c) CF3CO2H (d)

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

15. Which of the following presents the correct order of the acidic strength in the given compounds

(A) FCH2COOH > CH3COOH > BrCH2COOH > ClCH2COOH

(B) BrCH2COOH> ClCH2COOH > FCH2COOH > CH3COOH

(C) FCH2COOH >ClCH2COOH > BrCH2COOH > CH3COOH

(D) CH3COOH > BrCH2COOH > ClCH2COOH > FCH2COOH

Answer Key

1. B 2. B 3. B 4. C 5. C 6. A 7. B
8. D 9. B 10. D 11. B 12. A 13. D 14. B
15. C
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 GENERAL ORGANIC CHEMISTRY
®
DPP-7
JEE [MAIN + ADV.] DIVISION
SINGLE CORRECT QUESTION
1. Correct order of basic strength:

NH2 NH2
Me
(A) (B) Me2NH < Me3N in aqueous medium
<

(C) < (D) All of these

N N
H
2. Correct decreasing order of basic strength is:
NH2

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

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

3. Arrange following compound in order of increasing basic strength.

NH2 CH2–NH2

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

4. Which of the following is the correct order of base strength?

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

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

5. Correct order of basicity is:

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

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

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6. Value of pKa will be minimum for

OH OH
OH OH

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

OCH 3
NO2
COOH

7. Weakest base amongst the following is

NO2 O2N NO2

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

N N
H N
H H
8. What is the decreasing order of strength of the bases,

OH , NH2 , , CH3–CH2
(I) (II) (III) (IV)
(A) IV > II > III > I (B) III > IV > II > I
(D) I > II > III > IV (D) II > III > I > IV

9. The strongest base is :

(A) (B)

(C) (D) CH3–NH–CH3

10. (I) NH2 (II) CH3O NH2

(III) NO2 NH 2 (IV) NH2

NO2
The correct order of decreasing basicity of the above compound is :
(A) I > II > III > IV (B) II > I > IV > III
(C) III > IV > II > I (D) II > I > III > IV

11.

The basic strength of I, II and III decreases in the order

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

12. Which of the following is most basic :

Me Me
NH2 N
CH3 Me Me
(A) (B) (C) (D)

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13. The correct order of increasing basic strength of the bases NH3, CH3NH2 and (CH3)2NH is :
(A) NH3 < CH3NH2 < (CH3)2NH (B) CH3NH2 < (CH3)2NH < NH3
(C) CH3NH2 < NH3 < (CH3)2NH (D) (CH3)2NH < NH3 < CH3NH2

14. Among the following the weakest base is :

(A) C6H5CH2NH2 (B) C6H5CH2NHCH3 (C) O2NCH2NH2 (D) CH3NHCHO

Answer Key
1. C 2. A 3. D 4. C 5. C 6. C 7. D
8. A 9. B 10. B 11. B 12. D 13. A 14. D
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 GENERAL ORGANIC CHEMISTRY
®
DPP-8
JEE [MAIN + ADV.] DIVISION
SINGLE CORRECT QUESTION
1. Consider the following three halides :
(A) CH3–CH2–Cl (B) CH2=CH–Cl (C) C6H5–Cl
Arrange C–Cl bond length of these compound in decreasing order :
(A) A > B > C (C) A > C > B (B) C > B > A (D) B > C > A

2. Which of the following  bonds (C–H) participate in hyperconjugation :

(II)
H CH2–H
(I)

H
(IV)
(III) (V)
H H
(A) II, III, IV (B) I, IV, V (C) I, II, IV, V (D) II, IV, V

3. Compare heat of hydrogenation of the following :

(i) (ii) (iii)

(A) i > ii > iii (B) iii > ii > i (C) ii > iii > i (D) ii > ii > iii
4. Which of the following will have maximum Heat of combustion per CH2.

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

5. Which of the following has highest heat of hydrogenation.

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

6. Out of the following which has the minimum heat of hydrogenation.

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

7. Maximum heat of combustion will be

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

(C) CH3–CH2–CH = CH–CH2–CH3 (D) CH 3  C  C  CH 2  CH 3

| |
H 3C CH 3
8. Correct order of HOH is
(i) (ii) (iii) (iv)
(A) (ii) > (i) > (iii) > (iv) (B) (i) > (ii) > (iii) > (iv)
(C) (ii) > (i) > (iv) > (iii) (D) (i) > (ii) > (iv) > (iii)

9. Heat of combustion should be maximum for

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

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10. Which of the following should have highest heat of hydrogenation ?

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

11. In which pair Ist compound has higher resonance energy than IInd compound?

(A) , (B) ,

(C) , (D) ,
S O

12. Resonance energy order of , is

N S O
H
(I) (II) (III)
(A) I > II > III (B) I > III > II (C) II > I > III (D) III > I > II
13. Find correct order of resonance energy for

(I) OCH3 (II)

OCH3

(III) OCH3
(A) III > I > II (B) II > I > III (C) I > II > III (D) III > II > I

14. Which of the following has high resonance energy than ?

(A) (B)

(C) (D)

15. Which one of the following is having resonance energy of Ist more than IInd.

 
(A) (B)

(C) (D)
 

16. Which one of the following is having resonance energy of Ist more than IInd.
(A) C = C – NH – C = C – C = C & C = C – C = C – C = C – NH2


(B) & (C) &

O O 
O O
(D) None of these

Answer Key
1. A 2. D 3. B 4. A 5. C 6. B 7. D
8. D 9. C 10. C 11. C 12. C 13. C 14. D
15. C 16. D
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