general organic chemistry part 2

AtoZ Chemistry General Organic Chemistry – Part 2

RISHI SIR [B.TECH. IIT KANPUR] www.atozchemistry.com Be Topper with Topper in Chemistry in JEE Main & JEE-ADV Contact No. +91 9852476717

44

General Organic Chemistry – Part 2

1. Hyperconjugation

Q 1. The correct order of strength of substituent effect

(1) Hyperconugation (2) Mesomeric effect

(3) Inductive effect (4) Steric effect

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

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

Q 2. Hyperconjugation is due to

(a) Sigma sigma conjugation

(b) pi –pi conjugation

(c) sigma – pi conjugation

(d) none of these

Q 3. The magnitude of no bond resonance energy is

directly proportional to the

(A) No. of sigma bond around double bond

(b) No. of pi bond around sigma bond

(c) No. of hydrogen atoms in a molecule

(d) No. of hyperconjugable hydrogen atoms

Q 4. The electron donating capacity through

Hyperconjugation is

(A)– CH3 > -CH2 –CH3 > -CH(CH3)2 > -C(CH3)3

(B) - CH2–CH3 > -CH(CH3)2 > -C(CH3)3 > –CH3

(C) -C(CH3)3 > -CH(CH3)2 > -CH2–CH3 > –CH3

(D) -CH(CH3)2 > -C(CH3)3 > –CH3 > -CH2–CH3

Q 5. Hyyperconjugation phenomenon is possible in

(A) (B) 2 2CH CH=

(C) 6 5 2C H CH CH− =

(D) 3 2 2CH CH CH CH− − −

Q 6. Stability of following alkenes in the increasing

order is

(I) (II)

(III) (IV)

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

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

Q 7. The number of no. bond resonance structure is

equal to

(A) No. of hyperconjugable hydrogen atoms

(B) No. of hyperconjugable hyrgoen atom + 1

(C) No. of hyperconjugable hyrgoen atom + 2

(D) No. of hyperconjugable hyrgoen atom + 3

Q 8. The total number of contributing structure

showing hyperconjugation for the following

carbocation is [JEE Adv 2011]

Q 9. Which of the following show hyperconjugation?

(A) CH3 – CH =CH2 (B) CH2 = CH – CCl3

(C) CH3 – CH = CH – CH3

(D) (Me)2C = CH – CH3

(E) (F) (G)

(H) CH3 – CH2+ (I) CH3 – CH2

–

Q 10. Among the following pairs, which has higher no-

bond resonance energy?

(A)

(B)

(C)

(D)

Q 11. Consider the following species

Hyperconjugation occur in [CBSE PMT 2015]

(A) I Only (B) II Only

(C) III Only (D) I & III

CH – CH = CH3 2and C = CH2

CH3

CH3

CH3

And

CH3

CH – CH = CH3 2And CH – CH3 2

CH – CH = CH3 2And CH – CH3 2

•

•

CH3

(III)

CH – C – CH3

•

CH3

CH3

Ph – C – Ph•

Ph

(I)

(II)

H3C

CH2CH3

http://www.atozchemistry.com/



45

Q 12. The correct bond length between first carbon and

among the following is

(I) CH3 – CH2 – CH2 – CH3

(II) CH3 – CH2 – CH =CH2

(III) CH3 – CH =CH – CH3

(A) I ≈ II > III (B) I ≈II≈III

(C) I > II > III (D) I > II ≈ III

Q 13. The C-C bond length in propene is little shorter

149 pm then the C–C bond length 154 pm in

ethan. This is due to

(A) +I effect of 3CH group

(B) Mesomeric effect

(C) Electromeric effect

(D) Hyper conjugation effect

Q 14. Which of the following molecule has longest

C C= bond length ?

(A) 2 2CH C CH= = (B) 3 2CH CH CH− =

(C) (D)

Q 15. Correct order of bond length of indicated C H−

in the given

(A) a b c d (B) a d c b

(C) d a b c (D) b a c d

2. Effect of Hyperconjugation

Q 1. Which of the given is most stable carbocation

(A) (B)

(C) (D)

Q 2. Which of given is correct stability order

(A) (B)

(C) (D)

Q 3. The correct stability order is

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

(C) III II I (D) None of these

Q 4. The correct stability order of given cation

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

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

Q 5. The compound which gives most stable

carbonium ion on dehydration is [IIT JEE 1989]

(A)

(B)

(C)

(D)

Q 6. The least stable carbocation is

(A) (B)

(C) (D)

Q 7. Which of the given cation is least stable ?

CH – CH – CH OH3 2

CH 3

CH – C – OH3

CH 3

CH 3

CH – CH – CH – CH3 2 3

OHCH – CH – CH – CH OH3 2 2 2




46

(A) (B)

(C) (D)

Q 8. The most stable carbocation is

(A) (B)

(C) (D)

Q 9. The most stable alkene is

(A) (B)

(C) (D)

Q 10. How many hyperconjugative H atom is present in

the given cation ( )3 2 3CH CH C

(A) 9 (B) 3

(C) 5 (D) 7

Q 11. Stability order among these compounds is:

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

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

Q 12. Among the following pairs of alkenes, which is

more stable?

(A)

(B)

(C)

(D)

(E)

(F)

(G)

(H)

Q 13. Assertion (A): A compound with delocalized

electron is more stable than the compound where

Electrons were localized.

Reason (R): The extra stability of a compound

gains as a result of having delocalized electrons,

is called delocalization energy.

[AIIMS 2012]

(A) Both A & R are correct and R is the correct

explanation of A

(B) Both A & R is correct but R is not correct

explanation of A

(C) A is correct but R is Not correct

(D) Both A & R are not correct

Q 14. The heat of hydrogenation in the following

compound is in the order:

(I) CH ≡ CH, (II) CH2 = CH2,

(III) CH3 – CH = CH2

(IV) CH3–CH = CH– CH3

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

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

Q 15. The arrangement of decreasing order of

( )23 5 3 2CH ,C H , CH CH• • •

and ( )3 3CH C

•

stability of and free radical is

(A) ( ) ( )23 5 3 32 3CH C H CH CH CH C• • • •

CH3

H C3 CH3

CH3

CH3

CH3

CH = CH and CH – CH = CH2 2 3 2

C = C

CH3

CH3

CH3

H

And C = C

CH3

H

CH3

H

C = CH2

CH3

CH3

And C = C

CH3

H CH3

H

CH2

CH3

And

CH3

CH3

CH – CH = CH And CH – CH = CH – CH3 2 3 3

C = C

CH3

CH3

CH3

H

And C = C

CH3

H CH3

H

CH3

And

CH3

CH3

CH3

And

CH3

CH3

HC 3 CH 3




47

(B) ( ) ( ) 23 3 5 33 2CH C CH CH C H CH

• • • •

(C) ( ) ( )2 5 3 3 32 3C H CH CH CH CH C• • • •

(D) ( ) ( ) 23 3 3 63 2CH C CH CH CH C H

• • • •

Q 16. The arrangement of increasing order of stability

of and free radical is [AIEEE 2006]

(A) ( ) ( )6 5 2 6 5 3 3 33 2(C H ) CH (C H ) C CH C CH CH

• • • •

(B) ( ) ( )3 3 6 5 2 6 5 32 3CH CH CH C (C H ) CH (C H ) C

• • • •

(C) ( ) ( )3 3 6 5 3 6 5 22 3CH CH CH C (C H ) C (C H ) CH

• • • •

(D) ( ) ( )6 5 3 6 5 2 3 33 2(C H ) C (C H ) CH CH C CH CH

• • • •

3. Inductive Effect

Q 1. Inductive effect is due to

(A) σ – σ conjugation (B) σ bonds

(C) σ bonds polarization (D) none of these

Q 2. Inductive effect depends on

(A) Electronegativity of atoms

(B) Distance from the inductive centre

(C) both a and b are correct

(D) none of these

Q 3. Inductive effect involves

(A) Complete delocalization of − electrons

(B) Partial delocalization of − electrons

(C) Complete delocalization of − electron

(D) Partial delocalization of − electrons

Q 4. Choose correct statement

(A) I effect transfers e− from one carbon atom to

another

(B) I effect operates in both − bond

(C) I effect creates net charge in molecule

(D) I effect is distance dependent

Q 5. Which of them shown incorrect representation of

Inductive effect

(A) (B)

(C) (D)

Q 6. Which of the group can show + I effect?

(A) –COCH3 (B) –Ph

(C) –O– (D) –MgBr

Q 7. The correct order of inductive effect

(A) –F > -NO2 > -COOH > -Cl

(B) -NO2 > -F > -COOH > -Cl

(C) -NO2 > -COOH > -F > -Cl

(D) none of these

Q 8. The correct order of Order of - I effect is

(A) –N+H3 > -N+HMe2 > -NO2 > -CN

(B) -N+HMe2 > –N+H3 > -NO2 > -CN

(C) – N+H3 > -NO2 > -CN > -N+HMe2

(D) none of these

Q 9. The correct order of + I effect is

(A) –CH3 > -CH2–CH3 > -CH(CH3)2 > -C(CH3)3

(B) -CH2–CH3 > -CH(CH3)2 > -C(CH3)3 > –CH3

(C) -C(CH3)3 > -CH(CH3)2 > -CH2–CH3 > –CH3

(D) -CH(CH3)2 > -C(CH3)3 > –CH3 > -CH2–CH3

Q 10. Which one of the following orders is correct

regarding the –I effect of the substituents?

(A) 2NR OR F− − − (B) 2NR OR F− − −

(C) 2NR OR F− − − (D) 2NR OR F− − −

Q 11. What is the %s character in hybridization of

carbon when it exerts strongest I− effect

(A) 25% (B) 50%

(C) 75% (D) 100%

Q 12. Correct order of +I effect of given group

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

(C) II I III (D) I II III= =

Q 13. Correct order of –I effect of given group

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




48

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

Q 14. Which of the following order is correct regarding

– I effect of the substituents? [CBSE PMT 1998]

(A) 2NR OR F− − −

(B) 2NR OR F− − −

(C) 2NR OR F− − −

(D) 2NR OR F− − −

Q 15. Among the following pairs, which has greater +I

effect-

(A)

(B)

(C)

(D)

Q 16. Show the order of + I effect & explain the order:

O- , COO-, -CH3, -D, -H.

4. Mesomeric Effect

Q 1. Most stable cation is

(A) 2 2CH CH CH

= = (B) 3 2CH O CH

− −

(C) 2Ph CH

− (D) 3 2CH O CH

− −

Q 2. The most stable carbocation is [AIIMS 2017]

(A) (B)

(C) (D)

Q 3. The correct stability order of the following

species is [AIIMS 2016]

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

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

Q 4. Relative stability of the following carbocation is

[AIIMS 2016]

(A) 3C H+

(B) 3 2CH C H+

(C) 3 2CH OC H+

(A) C > B > A (B) C < B < A

(C) B > C > A (D) C < A > B

Q 5. The stability order of following carbocation is

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

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

Q 6. The most stable carbon free radical amongst the

following is

(A) (B) ( )3 2 2CH CH CH

•

(C) ( )3 2 3CH CH C

•

(D)

Q 7. The order of decreasing stability of the cations

(I) 3 3CH CHCH+

(II) 3 3CH CHOCH+

(III) 3 3CH CHCOCH+

is

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

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

Q 8. The most stable carbocation amongst the

following is

– C – CH3

CH3

CH3

And – CO

O

– O And – COO

– CH – CH – CH – CH And – CH – CH2 2 2 3 2

CH3

CH3

– CH

CH3

CH3

And – CH – CH2

CH3

CH3

O O

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

(I)

(II)

CH2

(III)

CH2

(IV)

CH2

CH2– CH2




49

(A) 3 2CH CH

(B) 3CH C O

=

(C) 3CH C NH

− = (D) ( )3 2CH C


following is

(A) (B)

(C) (D)

Q 10. The correct order of stability of carbocation

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

(C) II III IV I (D) None of these


following is

(A) (B)

(C) (D)

Q 12. Correct order of stability is

(A) I II III IV V

(B) V IV III II I

(C) V I II III IV

(D) IV III II I IV

Q 13. The most stable carbonium ion among the

following is [IIT JEE 1995S]

(A) 2 6 4 2P O N C H CH+

− − −

(B) 6 5 2C H CH+

−

(C) 6 4 2P Cl C H CH+

− − −

(D) 3 6 4 2p CH O C H CH+

− − −

Q 14. The most stable carbanion among the following is

(A) 2 6 4 2P O N C H CH

− − − (B) 6 5 2C H CH

−

(C) 6 4 2P Cl C H CH

− − −

(D) 3 6 4 2p CH O C H CH

− − −

Q 15. Ease of deprotonation by the use of base will be

maximum in which of the following compounds:

(A) (B)

(C) (D)

Q 16. How many sites are available for CH3O– attack

on

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

Q 17. Ease of ionization to produce carbocation &

Bromide ion will be maximum in which of the

following compounds

CH2

CH3

CH2

CH3

CH2

CH3

H C CH3

CH2(I) Ph – CH2

(II)

CH2(III)

CH – O – CH3 2

(IV)




50

(A)

(B)

(C)

(D)

Q 18. The correct order of reactivity of the following

compounds towards electrophile

(I) CH3O–CH= CH2 (II) CH2=CH2

(III) CH2 = CH–F (IV) CH2=CH–Cl

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

(C) I > II > IV > III (D) None of these

5. Steric effect, Electromeric Effect

Q 1. Which of the properties is/are not affected by

electromeric effect ?

(A) Reactivity in chemical reaction

(B) Orientation in chemical reaction

(C) Physical properties

(D) All properties are effected

Q 2. In electronic effect, which type of bond

participates?

(A) Single bond (B) − bond

(C) − bond (D) None of these

Q 3. Which of the following species has negative

electromeric ( )E− effect ?

(A) Electrophile (B) Nucleophile

(C) Acid (D) Lewis acid

Q 4. Which of the following species have positive

electromen ( )E+ effect?

(A) Electrophile (B) Nucleophile

(C) Base (D) lewis base

Q 5. The effect which causes a temporary polarisation

in the substrate molecule at the seat of a multiple

bond by shift of an electron pair from one atom to

the other under the influence of electrophilic

agent is called

(A) Inductive Effect (B) Electromeric Effect

(C) Photoelectric Effect (D) Crompton Effect

Q 6. Which is correct for electromeric effect ?

(A) it is a temporary effect

(B) it is the property of bond

(C) it takes place in presence of reagent, i.e.

electropile or nucleophile

(D) all are correct

Q 7. Steric inhibition of resonance can be expected in

(A) (B)

(C) (D)

Q 8. Consider the following two structures and chose

the correct statements

(A) C – N bond length structure I is greater than

that in structure II

(B) C – N bond length in structure I is less than

than in structure II

(C) C – N bond length in both structure is same

(D) It can not be compared

Q 9. In which of the given lone pair of nitrogen is not

participated in resonance

(A) (B)

NOO

(I)

NOO

(II)




51

(C) (D) None of these

Q 10. In which of the given resonance between two

benzenoid ring is not possible

(A)

(B)

(C)

(D) None of these

6. Carbocation & its rearrangement

Q 1. Which of the following statement is true?

(A) A reaction can happen without Transition

state but can’t happen without reactive

intermediate.

(B) Reaction can’t happen without Transition

state but can happen without reactive

intermediate.

(C) A reaction can’t happen without Transition

state & reactive intermediate.

(D) A reaction can happen without Transition

state & reactive intermediate.

Q 2. No. of reactive intermediate in a chemical

reaction involving n steps is equal to

(A) n (B) n – 1

(C) n + 1 (D) none of these

Q 3. A two step exothermic process with first step as

Rds can be represented as

(A) (B)

(C) (D)

Q 4. Stability order of these cations is

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

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

Q 5. Arrange the following carbonium ions in order of

increasing stability and give your answer?

(a) MeCHMe > CH2=CHCH2 > MeCH2CH2

(b) MeCH2CH2+ > MeCH+Me > CH2=CHCH2

+

(c) CH2=CHCH2+ > MeCHMe > MeCH2CH2

+

(d) CH2=CHCH3+> MeCH2CH2 > MeCHMe

Q 6. Consider the following carboncations

The relative stabilities of these carbonations are

such that

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

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

Q 7. Which one among the following carbocations has

the longest half-life ?

Q 8. Which is the most stable carbonation?

(A) ( )3 2CH CH+

(B)

E

R.C

E

R.C

E

R.C

E

R.C




52

(C) 2 2CH CH CH+= − (D) ( )3 3CH C+

Q 9. Decreasing order of stability of given

carbocations is

(I) (II) 2 2CH CH CH

= −

(III) 6 5 2C H CH

− (IV) 3 3CH CH CH

− −

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

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

Q 10. The most stable free radical is

(A) (B)

(C) (D)

Q 11. Find the stability order among the following

carbocations

(1) CH3-CH2 +, HO–CH2+, CH3–CO–O–CH2

+ ,

CH3–CO–CH2 +

(2) CH3–CH2+, CH3–NH–CH2

+ , C2H5–CH2+,

CH3–CO–NH–CH2+

(3) CH3+, CH2 =CH+ , HC≡C+

Q 12. Do the carbocation rearrangement in the

Following.

CH3

(A) H2C+ (B)

CH2+

(C) C2H5 – C(Ph)(CH3) – CH2+

Q 13. In following questions, two alternative

rearrangements are shown for each carbocations.

One of the two does not occur. Pick up the

correct one and justify your answer.

(A)

(B)

(C)

(D)

Q 14. The carbocation ion arrangement of

is

(A) (B)

(C) (D)

CH3

CH3

CH2

CH3CH2

CH3

CH2

CH3

CH2




53

7. Carbanion & its stability

Q 1. Draw an orbital Diagram for

(a) H2C = CH+ (b) H2C = CH –

Q 2. Indicate the hybridization of marked atoms in

each of the following species.

(A)

(B)

(C)

(D)

Q 3. Assertion (A): The correct order of stability of

Carbanion is

6 5 3 6 5 2( ) ( )C H C C H CH Allylcarbanion− −

3 3 2( )CH CH CH− −

Reason (R): The stability of carbanion is affected

both resonance and inductive effect.

[AIIMS 2014]


explanation of A


explanation of A



Q 4. Arrange the carbanions

( )3 3 3 2 6 5 23CCl , CH C,(CH ) CH,(C H )CH− − − −

In order of decreasing stability [AIEEE 2009]

(A) ( )3 2 3 6 5 2 3 3(CH ) CH CCl (C H )CH CH C

− − − −

(B) ( )3 6 5 2 3 2 3 3CCl (C H )CH (CH ) CH CH C− − − −

(C) ( )3 3 2 6 5 2 33CH C (CH ) CH (C H )CH CCl

− − − −

(D) ( )6 5 2 3 3 3 23(C H )CH CCl CH C (CH ) CH

− − − −

Q 5. Stability order of these carbanions is

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

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



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


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


Q 8. Stability order of these anions is

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

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

Q 9. The most stable carbanion among the following is

(A) 2 6 4 2p O N C H CH

− − −

(B) 6 4 2C H CH

−

(C) 6 4 2p Cl C H CH

− − −




54

(D) 3 6 4 2p CH O C H CH

− − −

Q 10. Which of the following carbanion is most stable?

(A) (B)

(C) (D)

Q 11. Which one of the following resonating structures

of 1-methoxy-1,3-butadiene is least stable?

(A) 2 3CH CH CH CH O CH

− = − = −

(B) 2 3H C CH CH CH O CH

= − − = −

(C) 2 3CH CH CH CH O CH

− − = − −

(D) 2 3H C CH CH CH O CH

= − − − −

Q 12. The least stable carbanion is

(A) (B)

(C) (D)

Q 13. The most stable carbanion is

(A) (B)

(C) (D)

Q 14. The correct stability order of following carbanion

is

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

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

Q 15. The stability of carbanions in the following

(I) RC C−

(II)

(III) 2R C C H−

= (IV) 3 2R C C H−

−

Is in order of [CBSE PMT 2008]

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

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

Q 16. The hybridization of carbon in 3CCl

is

(A) 2sp (B)

3sp

(C) sp (D) 3sp d

8. Free Radicals, Carbene, Nitrene

Q 1. The radical is aromatic because

It has [CBSE PMT 2013]

(A) 6p – orbitals & 6 unpaired electrons

(B) 7p – orbitals and 6 unpaired electrons

(C) 7p – orbitals and 7 unpaired electrons

(D) 6p – orbitals and 7 unpaired electrons

Q 2. The most stable carbon free radical amongst the

following is

(A) (B) ( )3 2 2CH CH CH

•

(C) ( )3 2 3CH CH C• (D)

Q 3. Stability order of the following radical is

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

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

O

I

O

II

OIII

IV




55

Q 4. The most stable free radical among the following

(A) 6 5 2 2C H CH CH•

(B) 6 5 3C H C HCH•

(C) 3 2CH CH•

(D) 3 3CH CHCH•

Q 5. In ( )3

t Bu C− , the hybridization of central

carbon atom is

(A) sp (B) 2sp

(C) 3sp (D) None of these

Q 6. Which free radical is the most stable one?

(A) (B)

(C) ( )3 3CH C

•

(D) ( )3 2CH CH

•

Q 7. Correct stability order of given radical is

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

(C) III II I IV (D) None of these

Q 8. Rank the following radicals in order of

Decreasing stability

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

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

Q 9. For the following

Correct order of stability


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

Q 10. In which of the following pairs, first member is

more stable than the second ?

(A)

(B) (C)

(D)

Q 11. Assertion (A): A free radical is a paramagnetic

Species.

Reason (R): A free radical is formed by

hemolytic fusion of covalent bond

[AIIMS 2013]


explanation of A


explanation of A



Q 12. The correct stability order of siglet carbine is

(I) 2: CF (II) 2: CCl (III) 2: CBr (IV) 2: Cl


(C) IV I II III (D) None of these

Q 13. The most stable singlet nitrene is

(A) 2Ph CH N :− − (B) 3CH O N :− −

(C) Ph N :− (D) 2O N CH CH O N :− = − −

Q 14. Which carbone is more stable ?

(A) Singlet (B) Triplet

(C) Doublet (D) Not stable at all

Q 15. Triple Nitrene has

(A) 2 l.p. of electrons

(B) 4 unpaired electrons

(C) 1 l.p. of electrons & 2 unpaired electrons

(D) 2 unpaired electrons

Q 16. Give the products in the following reactions

(A) PhH2C – CHBr2 Base;

⎯⎯⎯⎯→

(B) (Ph)3C – CHBr2 Base;

⎯⎯⎯⎯→

(C) (Ph)2BrC – CHBr2 Zn;

⎯⎯⎯→

(D) (Ph)2HC – CHBr2 Zn;

⎯⎯⎯→

(E) H2C=C=O

⎯⎯→

(F) RCONHBr Base;

⎯⎯⎯⎯→




56

9. Acidic Strength

Q 1. The correct acidic strength order for

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

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

Q 2. The correct acidic strength order is

(I) 3 2CH CH OH− − , (II)

3 3( )CH CH CH OH− − ,

(III) C(CH3)3-OH

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

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

Q 3. The correct order of acidic strength among the

following compound is

, , ,

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

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

Q 4. The correct order of acidic strength among the

following compound is

(I) (II) (III)

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

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

Q 5. Arrange the given phenols in their decreasing

order of acidity

(I) 6 5C H OH−

Select the correct answer from the given code:

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

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

Q 6. Which one of the following is the most acidic ?

(A) (B)

(C) (D) 2 3CH CH CH= −

Q 7. The correct order of acidic strength of given

compound is

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

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

Q 8. Which one of the following compound would you

expect to be the strongest acid?

(A) ( )2 2 5 2CH COOC H (B)

(C) 3 2 2 5CH COCH COOC H (D)

Q 9. Which of the given is most acidic ?

(A) Benzoic acid (B) Phenol

(C) Formic acid (D) p-nitrophenol

Q 10. Consider the following compounds

Write the correct decreasing order of acidic

strength. [AIIMS 2018]

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

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

Q 11. Correct order of increasing acidic strength is

[CBSE PMT 1994]

(A) H2O, C2H2, H2CO3, Phenol

(B) C2H2, H2O, H2CO3, Phenol

(C) Phenol, C2H2, H2CO3, H2O

(D) C2H2, H2O, Phenol, H2CO3

Q 12. Arrange the following compounds in decreasing

order of their acidic strength

F – CH – CH OH2 2

I

O N – CH – CH OH2 2 2

II

Br – CH – CH OH2 2

III

H N – CH – CH – OH3 2 2

IV

CH COOH3

I

CH CH OH3 2

II

C H OH6 5

III

C H SO H6 5 3

IV

COOH

COOH

CH2

COOH

COOHCH – COOH2

CH – COOH2

COOH

OCH3

COOH COOH

Cl

(I) (II) (III)




57

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

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

Q 13. The correct order of acidic strength of given

compound is

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

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

Q 14. The correct acidic strength order is

(I) HC≡CH (II) (III) CH2=CH2



Q 15. In the following compounds

OH OH

CH3

OH

NO2

OH

NO2

(I) (II) (III) (I

>

)

The order of acidity is [IIT JEE 1996]

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

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

Q 16. Acidity order of indicated H atoms in following

molecule is

(A) Ha> Hb> Hc (B) Hb> Hc>Ha

(C) Hb > Ha > H c (D) Ha > Hc > Hb

Q 17. Which of the following has the most acidic

hydrogen? [IIT JEE 2000S]

(A) 3-Hexanone (B) 2,4-Hexanedione

(C) 2,5-Hexanedione (D) 2,3-Hexanediaone

10. Acidic Strength & Basic Strength

Q 1. Which of the following cation is most acidic?

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

Q 2. Which of the following compound has the highest

apK value ?

(A) (B)

(C) (D)

Q 3. Arrange the following compounds in the order of

decreasing acidity

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

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

Q 4. The least acidic compound is




58

(A) (B)

(C) (D)

Q 5. The correct acidity order of the following is

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

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

Q 6. The correct basic strength among the following

compound is


(C) III II I (D) None of these

Q 7. The correct order of basic strength among

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

(C) II III IV I

(D) both A & B in different conditions

Q 8. Basic strength of

(I) 3 2H C C H−

(II) 2H C C H−

=

(III) HC C−

Is in order of [CBSE PMT 2008]

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

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

Q 9. The correct basic strength order among the

following is

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

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

Q 10. The correct order of basic strength among the

following

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

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

Q 11. The correct order of basic strength among the

following is

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

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

Q 12. The correct basic strength among the following is


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


(I) (II)

(III) (IV)

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

(C) IV III I II (D) None of these

R – NH2 Ph – NH2 R – C – NH2

O

IIIIII

NH3 MeNH2 Me NH2 Me N3

IVIIIIII

O

N

H

N

H

:

N

Me

:

I II III

I

NH2

II

NH2

III

N

H

CH – C – NH3 2

O

I

CH – CH – NH3 2 2

II

CH – C – NH3 2

NH

III

H N–C–NH2 2

NH

IV

N

:

H

N

:

NH2

I II III

N

:

H

N:

N

H

N

CH3

:

N

H

:




59

Q 14. Consider the following bases

(I) o-nitroaniline (II) m-nitroaniline

(III) p-nitroaniline

The decreasing order of basicity is

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

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

Q 15. Consider the basicity of the following aromatic

amines

(I) aniline (II) p-nitroaniline

(III) p-methoxyaniline (IV) p-methylaniline

The correct order of decreasing basicity is

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

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


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

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


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

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


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

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

Q 19. Arrange in increasing pKb

(a) 2 2HC C CH NH − −

(b) 2 2 2CH CH CH NH= − −

(c) 3 2 2 2CH CH CH NH− − −

(A) c b a (B) a b c

(C) b c a (D) b a c

Q 20. The correct order of decreasing basicity of the

compounds

(I) ( )3 3F C N

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

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

Q 21.

Correct order of basicity is

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

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


(A) 1 2 4 3 5 6

(B) 1 2 3 4 5 6

(C) 1 2 4 3 6 5

(D) 1 2 3 4 6 5

Q 23. The correct order of increasing Basicity of the

given conjugate base is [AIEEE 2010]

(A) 2RCOO HC C R N H− − − −

(B) 2R HC C RCOO N H− − − −

(C) 2RCOO N H HC C R− − − −

(D) 2RCOO HC C N H R− − − −

CH CH , CH = CH¯3 2 2

–

(1) (2)

HC C¯ NH ¯2

(3) (4)

NH3 OH¯

(5) (6)




60

11. Acid, Base & Electrophile, Nucleophile

Q 1. Identify the species not capable of acting as an

electrophile

(A) 3BCl (B) 3AlCl

(C) 4NH+ (D) 2CO

Q 2. Which of the following species is a nucleophile

but not an electrophile ?

(A) 4NH

(B) 3NH OH

−

(C) 3H O (D)

Q 3. Which of the following species cannot function

as an electrophile?

(A) 3H C (B) 2CCl

(C) 4SiF (D) 3H O

Q 4. Which of these species is capable of acting as

electrophile ?

(A) 2CO (D)

(C) 3AlCl (D) All of these

Q 5. The species in which nitrogen atom behaves as

electrophile as well as nucleophile is

(A) 2NO

(B) CN

(C) NO (D) 3NO

Q 6. Which of the following reaction intermediates are

electrophilic in character ?

(1) Carbocation (2) Cartanion

(3) nitrenes (D) Carbenes

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

(C) (3) and (4) (D) (1) and (4)

Q 7. The correct statement about electrophile is

[NEET 2017]

(A) Electrophile is a negatively charge species

and can form a bond by accepting a pair of

electrons from a nucleophile

(B) Electrophile is a negatively charge species

and can form a bond by accepting a pair of

electrons from another electrophile

(C) Electrophile are generally Neutral species and

can form a bond by accepting a pair of electrons

from nucleophile

(D) Electrophile can be either positively or

Neutral species and can form a bond by accepting

a pair of electrons from nucleophile

Q 8. Which of the following has the highest

nuceophilicity? [IIT JEE 2000S]

(A) F- (B) OH- (C) CH3- (D) NH2

-

Q 9. Among the following the strongest nucleophile is

[AIIMS 2009]

(A) 2 5C H S − (B) 3CH COO−

(C) 3 2CH NH (D) 2

NCCH −

Q 10. Rate of the reaction

Is fastest when Z is [AIIMS 2015]

(A) Cl– (B) 2

NH −

(C) 2 5C H O− (D) 3CH COO−

Q 11. Assertion (A): Aniline is better Nucleophile than

Anilinium ion.

Reason (R): Anilinium ions have positive charge

[AIIMS 2014]


explanation of A


explanation of A



Q 12. Which one of the following is an electrophile ?

(A) Boron trifluoride (B) Ethylene

(C) Benzene (D) Water

Q 13. Which one of the following pairs represents a set

of electophiles ?

(A) Br+ and CCl3 (B) AlCl3 and Cl-

(C) H+ and H2O (D) CN- and NH3

Q 14. Consider the following statements about

nucleophiles :

1. Nucleophiles have an unshared electron pair

and can make use of this to react with an electron

deficient species

2. Strength of nucleophiles generally increases on

C

O

ZR + Nu¯ C

O

NuR + Z¯




61

going down a group in the periodic Table

3. Cyanide ion is an ambident nucleophile which

may react either on C or N

Which of these statements are correct?

(A) 1, 2 and 3 (B) 2 and 3

(C) 1 and 3 (D) 1 and 2

Q 15. The electrophilic centres (s) in the molecule

1 2 3 4

CH2 = CH -CO-CH3 is / are

(A) C3 only (B) C1 and C3

(C) C1 and C2 (D) C2 and C4

Q 16. In the following groups the order of leaving

groups ability is [IIT JEE 1997S]

-OAc -OMe -SO2Me -OSO2CF3

I II III IV

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

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

Q 17. The correct leaving group tendency is

(A) F Cl Br I− − − −

(B) I Br Cl F− − − −

(C) Cl F Br I− − − −

(D) Cl Br F I− − − −

Q 18. Nucleophilic /Electrophilic property is

(A) Kinetically controlled

(B) Thermodynamically controlle

(C) Stoichiometry controlled

(D) None of these

Q 19. Nucleophilic strength is maximum in

(A) 2H O (B) Ethanol

(C) 2CS (D) 3CH OH

Answer Key

1. Hyperconjugation

(1). B (2). C (3). D

(4). A (5). D (6). A

(7). B

(8). 6 (9). A, C, D, E, F, H

(10). A – II, B – II, C – II, D – II

(11). C (12). A (13). D

(14). D (15). B

2. Effect of Hyperconjugation

(1). A (2). D (3). C

(4). A (5). B (6). D

(7). C (8). B (9). D

(10). B (11). B

(12). A – II, B – I, C – I, D – II,

E – II, F – I, G – I, H – II

(13). A (14). A (15). C

(16). B

3. Inductive Effect

(1). C (2). C (3). B

(4). D (5). D (6). D

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

(10). C (11). B (12). A

(13). B (14). C

(15). A – I, B – I, C –II, D – II

(16). SEE NOTES

4. Mesomeric Effect

(1). D (2). D (3). D

(4). A (5). C (6). C

(7). B (8). C (9). D

(10). C (11). A (12). C

(13). D (14). A (15). B

(16). B (17). B (18). B




62

5. Steric effect, Electromeric Effect

(1). C (2). C (3). B

(4). A (5). B (6). D

(7). C (8). B (9). C

(10). C

6. Carbocation & its rearrangement

(1). B (2). B (3). B

(4). B (5). C (6). A

(7). A (8). D (9). C

(10). D

(11). (1) HO–CH2+ > CH3–CO–O–CH2

+ >

CH3-CH2 + > CH3–CO–CH2 +

(2) CH3–NH–CH2+ > CH3–CO–NH–CH2

+ >

CH3–CH2+ > C2H5–CH2

+,

(3) CH3+ > CH2 =CH+ > HC≡C+

(12). Write the appropriate process

(13). (1) + (2)

+ CH3

(3) C2H5 – C+(CH3) – CH2 – Ph

(14). A

7. Carbanion & its stability

(1). See Notes

(2). A – SP2, B – SP2, C – SP2, D – SP2

(3). A (4). B (5). C

(6). D (7). C (8). A

(9). A (10). A (11). C

(12). A (13). D (14). D

(15). A (16). A

8. Free Radicals, Carbene, Nitrene

(1). C (2). C (3). A

(4). B (5). B (6). B

(7). C (8). A (9). A

(10). A, C (11). B (12). A

(13). B (14). B (15). C

(16). (A) PhHC = CHBr (B) (Ph)2C = CPhBr

(C) (Ph)2C = CHBr (D) (Ph)2C = CH2

(E) H2C: + CO (F) R–N=C=O

9. Acidic Strength

(1). B (2). A (3). B

(4). A (5). C (6). B

(7). C (8). B (9). C

(10). C (11). D (12). C

(13). C (14). D (15). D

(16). B (17). B

10. Acidic Strength & Basic Strength

(1). C (2). D (3). C

(4). A (5). A (6). A

(7). D (8). D (9). A

(10). B

(11). A (12). C (13). A

(14). A (15). A (16). D

(17). D (18). A (19). A

(20). B (21). D (22). C

(23). D

11. Acid, Base & Electrophile, Nucleophile

(1). C (2). B (3). D

(4). D (5). C (6). B, C, D

(7). D (8). C (9). A

(10). A (11). A (12). A

(13). A (14). A (15). B

(16). B (17). B (18). A

(19). C


general organic chemistry part 2

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