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BANSALCLASSES TARGET IIT JEE 2007 XII (ALL) QUESTION BANK ON ORGANIC CHEMISTRY ACIDITY, BASICITY H-BONDING

BANSALCLASSES

TARGET IIT JEE 2007

XII (ALL) QUESTION BANK ON
XII (ALL)
QUESTION BANK ON

ORGANIC CHEMISTRY

ACIDITY, BASICITY H-BONDING

&

TAUTOMERISM

ACIDITY, BASICITY, H-BONDING & TAUTOMERISM

Q.1

(a) Methyl alcohol reacts with BF 3 .

(b) Methyl chloride reacts with AlCl 3 .

(c) Dimethyl ether reacts with BF 3 .

Q.2

Write equations showing the Lewis acid-base reaction that takes place when

Which of the following are lewis acids & which are lewis bases?

(a)

CH CH

3

2

N ⋅ ⋅ − CH

|

CH

3

3

(b)

CH

3

CH

|

C

3

(c) (C 6 H 5 ) 3 P:

|

CH

3

(d)

Br

(e)

(CH 3 ) 3 B

(f) H :

Q.3

(a) CH 2 ClCO 2 H or CHCl 2 CO 2 H

(b) CCl 3 CO 2 H or CHCl 2 CO 2 H

(c) CH 2 FCO 2 H or CH 2 FCH 2 CO 2 H

Q.4

Which would you expect to be the stronger acid? Explain your reasoning in each instance.

Write equations for the acid base reaction that would occur when each of the following compounds or solution are mixed. In each case label the stronger acid & stronger base,& the weaker acid & weaker base.

(a) NaH is added to CH 3 OH

(b) NaNH 2 is added to CH 3 CH 2 OH

(c) Gaseous NH 3 is added to ethyl lithium in hexane

(d) NH 4 Cl is added to NaNH 2 in liq. NH 3

(e) (CH 3 ) 3 CONa is added to H 2 O

(f) NaOH is added to (CH 3 ) 3 C-OH

(g) C 2 H 5 OH is added to a solution of HC C Na + in liquid NH 3 .

Q.5

Q.6

Q.7

CH 3 CH 2 MgBr + CH 3 C CH → A + B

Choose the member of each of the following pairs of compunds that is likely to be the stronger base.

(a)

NH

2

or NH 3

(b) OH or H 2 O

(c) OH or SH

(d) CH 3 CH 2 O or

(c) OH – or SH – (d) CH 3 CH 2 O – or (e) CH

(e)

CH

2

O

||

C

OH

or CH 3 CH 2 O

(f) NH 3 or

NH

4

Choose the member of each of the following pairs of compunds that is likely to be the weaker base.

(a)

H 2 O or H 3 O

(d)

F , OH , NH 2 ,

CH

3

(b) H 2 S, HS , S 2

(e) HF, H 2 O, NH 3

(c) Cl , SH

(f) OH , SH , SeH

Q.8

Label the reactants in these acid – base reactions as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the recations.

(a) CH

(b)

CH

3

3

O

+

CH

• •

O

|

CH

+

CH

3

3

3

Cl

+

→

CH

3

• •

O

|

H

H

→

O

CH

3

CH

• •

O

|

3

CH

+

+

3

• •

Cl

• •

CH

3

• •

O

|

H

+

H

(c)

H

O

||

C

H

+

NH

3

→

H

O

|

C

|

H

+

NH

3

• •

N H

C l

(d)

(e) (CH 3 ) 3 CCl + AlCl 3 → (CH 3 ) 3 C + + AlCl 4

CH

3

2

+

CH

3

CH

2

→

CH

3

+

N H

2

CH CH

2

+

(f) CH 2 = CH 2 + BF 3 → B F − CH −
(f) CH 2 = CH 2 + BF 3 →
B
F
CH
C H
3
2
2
(g)
— +
(h) B F
CH
C H
+ CH 2 = CH 2 →
B F
CH
CH
3
2
2
3
2

(i)

CH 2 = CH 2 → B F − CH − CH 3 2 2 3
CH 2 = CH 2 → B F − CH − CH 3 2 2 3

2

CH

3

2

+

C l

+

C H

2

Q.9

Predict the products of the following acid_base reactions.

H 2 SO 4

+ CH 3 COO l

Q.10

(a) Predict the products of the following acid – base reaction. CH 3 CH 2 – OH + CH 3 – Li →

(b) What is the conjugate acid of CH 3 Li ? Would you expect CH 3 Li to be a strong base or a weak base ?

Methyllithium (CH 3 Li) is often used as a base in organic reactions.

Q.11

Which reagent in each pair listed here would be the more reactive Nu in a protic solvent ?

(a)

CH 3 NH or

CH 3 NH 2

(c)

CH 3 O or CH 3 COO

(e)

Ph 3 N or Ph 3 P

(g)

H 2 S or HS

(b)

(d)

(f)

(h)

H 2 O or H 3 O

CH 3 SH or

CH 3 COO or OH

NH 3 or

CH 3 OH

NH 4

Q.12

Each of these molecules is electrophile. Identify the electrophilic atom & draw a mechanism for reaction with a generalised nucleophile Nu , giving the product in each case.

(a)

Nu – , giving the product in each case. (a) (b) (c) (d) Cl – Cl

(b)

Nu – , giving the product in each case. (a) (b) (c) (d) Cl – Cl

(c)

Nu – , giving the product in each case. (a) (b) (c) (d) Cl – Cl

(d) Cl – Cl

(e)

the product in each case. (a) (b) (c) (d) Cl – Cl (e) B ansal C

Q.13

Each of these molecules is nucleophile. Identify the nucleophilic atom & draw a mechanism for reaction with a generalised electrophile E + , giving the product in each case.

(a) R – C C

(b)

(d)

the product in each case. (a) R – C ≡ C – (b) (d) (e) (c)

(e)the product in each case. (a) R – C ≡ C – (b) (d) (c) NH

(c) NH 2 – NH 2 2 – NH 2

(a) R – C ≡ C – (b) (d) (e) (c) NH 2 – NH 2

Q.14

(a) CH 3 NH 2 , CH 3

(b) CH 3 O , CH 3 NH ,

(c) CH 3 CH = CH , CH 3 CH 2

Arrange the following compounds in order of increasing basicity.

NH

3

, CH 3 NH

CH 3

CH

2

CH

2

, CH 3 CC

Q.15

Neither of these methods of making pentan-1,4 diol will work. Explain why not – what will happen instead?

(i) CHO–CH 2 –CH 2 –CH 2 –OH

MeMgBr

→

followed by H

+

CH

3

CH

|

OH

CH

2

CH

2

CH

|

2

OH

(ii) Br–CH 2 –CH 2 –CH 2 –OH

Mg

Et

2

O

MgBr–CH 2 –CH 2 –CH 2 –OH

CH CHO

3

→

followedby H

+

Q.16

Suggest what species would be formed by each of the following combinations :

(a)

PhO + CH 3 COOH

the following combinations : (a) PhO – + CH 3 COOH (b) (c) Pyridinium ion +

(b)

(c) Pyridinium ion + trifluoroacetate ion

+ CH 3 COO

Q.17

Say which pk a belong to which functional group in case of following amino acids :

(i) cysteine :

group in case of following amino acids : (i) cysteine : : 1.8, 8.3 & 10.8

: 1.8, 8.3 & 10.8

(ii) glutamic acid :

: (i) cysteine : : 1.8, 8.3 & 10.8 (ii) glutamic acid : : 2.19, 4.25,

: 2.19, 4.25, 9.67

Q.18

(a)

Record the following sets of compounds according to increasing

,
,

, cyclohexane carboxylic acid.

pK a ( = – log Ka)

(b) 1-butyne, 1-butene, butane

(c) Propanoic acid, 3-bromopropanoic acid, 2-nitropropanoic acid

(d) Phenol,o-nitrophenol, o-cresol

(e) Hexylamine,aniline,methylamine

Q.19

Explain which compound is the weaker base.

 

(a)

(a) or  

or

(a) or  
 

(b)

CH 2 = CH – CH = CH – CH 2 or CH 2 = CH – CH 2

 
 

O

O

O

O

 

||

||

||

||

(c)

O

C

C

OH

or

HO

C

C

OH

(d)

(d) or  

or

or
 

Q.20

Rank the following amines in increasing basic nature.

 

(a)

(a)    
 
(a)    
 
(a)    
(a)    
 

(i)

(ii)

(iii)

(iv)

(b)

(b)    
 
(b)    
 
(b)    
(b)    
 

(i)

(ii)

(iii)

(iv)

(c)

(c)    
 
(c)    
 
(c)    
 

(i)

(ii)

(iii)

Q.21

Dimethyl furmamide (DMF) is an example of polar aprotic solvent, aprotic meaning it has no hydrogen atoms attached to highly electronegative atoms.

(a)

Draw what you predict to be its most important resonance forms.

 

(b)

DMF when used as the reaction solvent, greatly enhances the reactivity of nucleophiles. e.g. NaCN + CH 3 CH 2 Br → CH 3 CH 2 C N + NaBr Suggest an explanation for this effects.

Q.22

Arrange the basic strength of the following compounds.

 

(a)

OH

 

CH 3 COO

 

Cl

(i)

 

(ii)

(iii)

(b)

CH C (i)

 

CH 2 = CH (ii)

CH 3 CH 2 (iii)

(c)

CH 2 = CHCH 2 NH 2 (i)

CH 3 CH 2 CH 2 NH 2 (ii)

CH C – CH 2 NH 2 (iii)

 

(d)

(e)

(f)

(d) (e) (f) (i) (i) Cl – (i) (ii) (iii) (ii) RCOO – (ii) OH –

(i)

(d) (e) (f) (i) (i) Cl – (i) (ii) (iii) (ii) RCOO – (ii) OH –

(i)

Cl

(i)

(ii) (iii)
(ii)
(iii)

(ii)

RCOO

(ii)

OH

(iii)

(iii)

RO

(iv)

NH 2

(v)

Q.23

(i)

Set the following in increasing order of pk b :

Q.23 (i) Set the following in increasing order of pk b : , (ii) CH 3

,

(i) Set the following in increasing order of pk b : , (ii) CH 3 NH

(ii) CH 3 NH 2 , (CH 3 ) 2 NH , (CH 3 ) 3 N , NH 3

(iii) ,
(iii)
,

(iv)

,3 ) 2 NH , (CH 3 ) 3 N , NH 3 (iii) , (iv)

) 2 NH , (CH 3 ) 3 N , NH 3 (iii) , (iv) ,

[In aqeous medium]

Q.24

(a)

(b)

(c)

Arrange the following in increasing acid strength :

( c ) Arrange the following in increasing acid strength : (i) (ii) CH 3 –

(i)

c ) Arrange the following in increasing acid strength : (i) (ii) CH 3 – OH

(ii)

CH 3 – OH 3 – OH

(i)

(ii)

increasing acid strength : (i) (ii) CH 3 – OH (i) (ii) (iii) (iii) CH 3

(iii)

acid strength : (i) (ii) CH 3 – OH (i) (ii) (iii) (iii) CH 3 −

(iii)

CH

3

O

||

C

(i)

OH

 

O

O

 

O

||

||

||

HO

C

C

OH

HO

C

CH CH

2

(ii)

(iii)

2

O

||

C

OH

Q.25

(i) Methane sulfonic acid, acetic acid & methanol.

(ii) CH 3 – CH 2 – CH 3 , CH 2 = CH – CH 3 , CH 3 – CHO , CHO – CH 2 – CHO , CH 4

(iii) CH 3 NO 2 , (NO 2 ) 2 – CH 2 , (NO 2 ) 3 – CH

Set the following in increasing order of pk a :

(iv)

CH Set the following in increasing order of pk a : (iv) , , (v) CH

,

Set the following in increasing order of pk a : (iv) , , (v) CH 3

,

Set the following in increasing order of pk a : (iv) , , (v) CH 3

(v) CH 3 COOH , NO 2 – CH 2 – COOH ,

CH

3

,

C − CH − C 2 || || O O
C
CH
C
2
||
||
O
O

OH

(vi) , , H H H H (vii) CHO – CH 2 – CHO ,
(vi)
,
,
H
H
H
H
(vii) CHO – CH 2 – CHO ,
CH
C
CH
3
||
O
Et
O
C
CH
C
CH
2
3
||
||
O
O

2

C

||

O

CH

3

,

Et

O

C

||

O

CH

2

C

||

O

O

Et

,

Cyanic acid (HO–CN) & isocyanic acid (H–N=C=O) differ in the positions of their electrons but their structure do not represent resonance structures.

(a) Explain

(b) Loss of a proton from cyanic acid yields the same anion as that obtained by loss of a proton from isocyanic acid. Explain.

Q.26

Q.27

Draw a mechanism for this reaction. PhCHBrCHBrCO 2 H + NaHCO 3 → PhCH=CH–Br + CO 2

Q.28

Arrange the increasing order of acidic strength of the following compounds.

(a)

(b)

order of acidic strength of the following compounds. (a) (b) (i) (i) (c) CH 3 OH

(i)

of acidic strength of the following compounds. (a) (b) (i) (i) (c) CH 3 OH (i)

(i)

(c) CH 3 OH

(i)

the following compounds. (a) (b) (i) (i) (c) CH 3 OH (i) (ii) CH 2 =CH–CH

(ii)

CH 2 =CH–CH 2 CO 2 H

(ii)

CF 3 OH (ii)

(iii)

CH 3 CH 2 CO 2 H

CCl 3 –OH (iii)

(iii)

Q.29

Explain which is a stronger acid.

(a) CH 3 CH 3 BrCH 2 NO 2

OH (c) or O=C–CH 3 (e) or
OH
(c)
or
O=C–CH 3
(e)
or

(b)

(d)

O O || || CH − C − CH & CH − C 3 3
O
O
||
||
CH
C
CH
&
CH
C
3
3
3
OH
or
O=C–CH 3

Q.30

Which of the following would you predict to be the stronger acid ?

(a) or
(a)
or
would you predict to be the stronger acid ? (a) or − CH CN 2 (b)

CH CN

2

(b) CH 3 – CH 2 – CH 2 – OH or CH 3 – CH = CH – OH

(c) CH 3 – CH = CH – CH 2 – OH or CH 3 – CH = CH – OH

Q.31

Q.32

Which is a stronger base? & Why.

(a)

ethylamine or aniline

(c)

phenoxide ion or ethoxide ion

(b) ethylamine or ethoxide ion (d) cyclohexylamine or aniline

The K a of phenylacetic acid is 5.2 × 10 5 , and the pK a of propionic acid is 4.87.

10 – 5 , and the pK a of propionic acid is 4.87. (a) Calculate the
10 – 5 , and the pK a of propionic acid is 4.87. (a) Calculate the
10 – 5 , and the pK a of propionic acid is 4.87. (a) Calculate the

(a) Calculate the pK a of phenylacetic acid and the K a of propionic acid.

(b) Which of these is the stronger acid?

(c) Predict whether the following equilibrium will favor the reactants or the products.

Q.33

Q.34

Q.35

Q.36

favor the reactants or the products. Q.33 Q.34 Q.35 Q.36 Explain why the 2-methylpyrrolidine boils at
favor the reactants or the products. Q.33 Q.34 Q.35 Q.36 Explain why the 2-methylpyrrolidine boils at

Explain why the 2-methylpyrrolidine boils at a higher temperature than its isomers N- methylpyrrolidine.

Although nitration usually causes elevation of B.P. yet the nitration of resorcinol to 2-nitroresorcinol decreases their B.P. then their parent compound.

o-nitrophenol is sparingly soluble in water & has lower B.P. but p-nitrophenol is completely soluble in water & has high boiling point.

When 30 ml of ethanol and 5 ml of water are mixed the volume of the resulting solution is less than 35 ml. Explain.

Q.37

Ammonium salts are much more soluble in water than are the corresponding sodium salts. Explain?

Q.38

HF has a dipole moment of 1.82 D, its boiling point is 19.34°C. Ethyl fluoride has an almost identical diploe moment & has a larger molecular weight, yet its B.P. is – 37.7°C. Explain.

Q.39

HCO 2 H & CH 3 CO 2 H exists as dimer. Explain.

 

Q.40

Cyclohexanol is more soluble in water then 1-hexanol.

Q.41

Explain why CH 3 OH and CH 3 CH 2 OH are reasonably good solvents for many ionic compounds compare the solvent properties of ethanol and pentanol towards ionic compound.

Q.42

1,5-Pentanediol is soluble & 1-Pentanol is slightly soluble in H 2 O.

 

Q.43

Compare the relative (i) Boiling points & (ii) Water solubilities of toluene & phenol.

 

Q.44

Which isomer (o, m or p) of hydroxacetophenone steam distills.

 

Q.45

Give structure for ethanolamine showing two different intramolecular H–bonds & discuss their relative strength.

Q.46

Which of the following system show H–bonding during tautomerism.

 

(a)

(a)
 

(b)

(a)   (b) (c) (d)

(c)

(a)   (b) (c) (d)

(d)

(a)   (b) (c) (d)

Q.47

Trans isomer of indigotin is stable w.r.t cis isomer. Explain.

 
 
 
 
 
   
 

Q.48

What is the attacking site of conjugate base of triketo form of phloroglucinol in protic & aprotic solvent.

Q.49

In each of the following pairs which is more stable :

 
(a) l (c) l (e) l
(a)
l
(c)
l
(e)
l

(b)

(d)

is more stable :   (a) l (c) l (e) l (b) (d) l l B

l

is more stable :   (a) l (c) l (e) l (b) (d) l l B

is more stable :   (a) l (c) l (e) l (b) (d) l l B

l

more stable :   (a) l (c) l (e) l (b) (d) l l B ansal

Q.50

In each of the following pairs which is less stable :

 

(a)

l (b) l l (d) l l
l
(b)
l
l
(d)
l
l

(c)

(e)

Q.51

In each of the following pairs which is more stable :

 

(a)

(a)  
 

(b)

(b) (c) l
(b) (c) l

(c)

(c)

l

(b) (c) l

(d)

(d) l (e) l

l

(d) l (e) l

(e)

(e)

l

(d) l (e) l

Q.52

In each of the following pairs which is less stable :

 

(a)

(c)

the following pairs which is less stable :   (a) (c) l l (b) (d) l

l

l

following pairs which is less stable :   (a) (c) l l (b) (d) l l

(b)

(d)

l
l

lpairs which is less stable :   (a) (c) l l (b) (d) l B ansal

which is less stable :   (a) (c) l l (b) (d) l l B ansal

Q.53

Q.54

Q.55

In each of the following pairs which will have higher enol content :

(a) CH 3 CHO and

which will have higher enol content : (a) CH 3 CHO and (b) and (c) (d)

(b)

andwill have higher enol content : (a) CH 3 CHO and (b) (c) (d) (e) and

(c)

(d)

(e)

andenol content : (a) CH 3 CHO and (b) and (c) (d) (e) and and In

enol content : (a) CH 3 CHO and (b) and (c) (d) (e) and and and
and and
and
and
: (a) CH 3 CHO and (b) and (c) (d) (e) and and and In each
: (a) CH 3 CHO and (b) and (c) (d) (e) and and and In each
: (a) CH 3 CHO and (b) and (c) (d) (e) and and and In each

In each of the following pairs which will have less enol content :

(a)

(c)

(e)

pairs which will have less enol content : (a) (c) (e) and and CH | Cl

pairs which will have less enol content : (a) (c) (e) and and CH | Cl

and

and

CH

|

Cl

2

CHO

less enol content : (a) (c) (e) and and CH | Cl 2 − CHO and
and CH 3 −
and CH
3 −

CHO

(b)

and(b)

(b) and

(d)

and(d)

(d) and

In each of the following pairs which will have higher enol content :

(a)

(c)

CH

|

NO

2

2

CHO and

CH

|

Cl

2

CHO

and: (a) (c) CH | NO 2 2 − CHO a n d CH | Cl

(a) (c) CH | NO 2 2 − CHO a n d CH | Cl 2

(b)

and(c) CH | NO 2 2 − CHO a n d CH | Cl 2 −

(d) and
(d)
and
2 − CHO a n d CH | Cl 2 − CHO and (b) and (d)
2 − CHO a n d CH | Cl 2 − CHO and (b) and (d)

Q.56

In each of the following pairs which will have less enol content :

 

(a)

(a) and   (b) and

and

(a) and   (b) and
 

(b)

(a) and   (b) and

and

(a) and   (b) and

(c)

and(c)   (d) and

(c) and   (d) and
 

(d)

(c) and   (d) and
(c) and   (d) and

and

(c) and   (d) and
(c) and   (d) and

(e)

and(e)  

(e) and  
 

Q.57

Which of the following compounds can exhibit tautoimerism :

 

(a)

CH 2 = C = O

(b) CH 2 = CH – OH

(c) HO – CH = CH – OH

 

(d)

CH 3 CN

(e)

(e)
 

Q.58

Which of the following compounds can not exhibit tautoimerism :

 

(a)

(a) (b)   (c)  

(b)

(a) (b)   (c)  
 

(c)

(a) (b)   (c)  
 

(d)

(d)   (e)  
 

(e)

(d)   (e)  
 

Q.59

Which of the following compounds can exhibit tautoimerism :

 

(a)

(a) (b) (c)   (d) (e)

(b)

(b)

(c)

(c)
 

(d)

(d) (e)

(e)

(a) (b) (c)   (d) (e)

Q.60

Which of the following compounds can not exhibit tautoimerism :

 

(a)

(a) (b) (c)  

(b)

(a) (b) (c)  

(c)

(a) (b) (c)  
 

(d)

(d)   (e) CH 3 – NO
 

(e) CH 3 – NO

Q.61

What is the relationship between these two molecules? Discuss the structure of the anion that would be formed by the deprotonation of each compound.

that would be formed by the deprotonation of each compound. B ansal C lasses Q. Bank

Q.62

Q.63

Q.64

Q.65

Q.66

Q.67

Q.68

5,5 – dimethylcyclohexane –1,3 –dione (dimedone) shows tautomerism.Write down tautomeric structure.

Draw enol forms of these carbonyl compounds and comment on the stability of the enol forms.

(a)

and comment on the stability of the enol forms. (a) (b) The proportion of enol in

(b)

and comment on the stability of the enol forms. (a) (b) The proportion of enol in

The proportion of enol in a sample of the two ketones below are shown. Why are they so different ?

(a)

4 × 10 – 4 % enol 4 % enol

(a)

are they so different ? (a) 4 × 10 – 4 % enol (a) and (b)

and

they so different ? (a) 4 × 10 – 4 % enol (a) and (b) Shows

(b)

Shows tautomeric forms of (a) & (b).

(b)

62 % enol(a) and (b) Shows tautomeric forms of (a) & (b). (b) Isatin was the first compound

Isatin was the first compound to show tautomerism.

62 % enol Isatin was the first compound to show tautomerism. What is the tautomeric form

What is the tautomeric form of isatin.

1, 3 – dicarbonyl compounds such as (A) are usually mostly enolized. Why is this ? Draw the enols available to compounds A & B comment on the different pattern of enolization.

(A)

& B comment on the different pattern of enolization. (A) (B) In each of the following

(B)

B comment on the different pattern of enolization. (A) (B) In each of the following sets

In each of the following sets of compounds write the increasing order of % enol content

(a)

(b)

write the increasing order of % enol content (a) (b) B ansal C lasses Q. Bank
write the increasing order of % enol content (a) (b) B ansal C lasses Q. Bank
write the increasing order of % enol content (a) (b) B ansal C lasses Q. Bank
write the increasing order of % enol content (a) (b) B ansal C lasses Q. Bank
write the increasing order of % enol content (a) (b) B ansal C lasses Q. Bank

Q.69

(c)

(d)

(e)

Q.69 (c) (d) (e) In each of the following sets of compounds write the decreasing order

In each of the following sets of compounds write the decreasing order of % enol content.

(a)

(b)

(c)

(d)

(e)

the decreasing order of % enol content. (a) (b) (c) (d) (e) B ansal C lasses
the decreasing order of % enol content. (a) (b) (c) (d) (e) B ansal C lasses
the decreasing order of % enol content. (a) (b) (c) (d) (e) B ansal C lasses
the decreasing order of % enol content. (a) (b) (c) (d) (e) B ansal C lasses
the decreasing order of % enol content. (a) (b) (c) (d) (e) B ansal C lasses
the decreasing order of % enol content. (a) (b) (c) (d) (e) B ansal C lasses
the decreasing order of % enol content. (a) (b) (c) (d) (e) B ansal C lasses
the decreasing order of % enol content. (a) (b) (c) (d) (e) B ansal C lasses
the decreasing order of % enol content. (a) (b) (c) (d) (e) B ansal C lasses

Q.70

Enol form of cyclobutanone is very unstable vs enol form of triketocyclobutane, which is very stable.

Q.71

has lower boiling point than

has lower boiling point than

has lower boiling point than

even when former has – OH group.

Q.72

Q.72

Among these give ease of enolization.

 

Q.73

% enol content of acetylacetone in following solvents is found as :

Solvent

% enol content

 

H 2 O

 

15

Liquid state

76

hexane

92

gas phase Explain the observation.

92

Q.74

Q.74
Q.74
Q.74
 
 
 
 
 
 
 
 

Explain the observation.

 

Q.75

Q.75 l

l

Q.75 l

This tautomeric system exist almost exclusively in favour of phenol and it is insensitive to change in solvent.

ANSWER KEY

Q.2

LA b,e LB acdf

Q.3

(a) 2; (b) 1; (c) 1

Q.5

CH 3 CH 3 + CH 3 C CMgBr

Q.6

(a) 1; (b) 1; (c) 1; (d) 1; (e) 2; (f) 1

Q.7

(a) 2; (b) 1; (c) 1; (d) 1; (e) 1; (f) 3

Q.11

(a) 1; (b) 1; (c) 1; (d) 1; (e) 2; (f) 2; (g) 2; (h) 1

Q.14 (a) 2<1<3; (b) 1<2<3; (c) 3<1<2

Q.18 (a) 3<2<1; (b) 1<2<3; (c) 3<2<1; (d) 2<1<3; (e) 2<3<1

Q.19

Q.20 (a) 3<2<1<4; (b) 1<2<3<4; (c) 3<1<2

Q.22 (a) 1>2>3; (b) 1<2<3; (c) 3<1<2; (d) 2<1<3; (e) 1<2<3; (f) 1<2<3<4<5

Q.23

Q.24 (a) 1<2<3; (b) 3>1>2; (c) 1<3<2 Q.25 (i) 1<2<3; (ii) 1>5>2>3>4; (iii) 1>2>3; (iv) 1>3>4>2; (v) 1>3>2; (vi) 2>1>3;

(a) 2; (b) 1; (c) 2; (d) 2

(i) 1>2; (ii) 4>3>1>2; (iii) 1<2; (iv) 1<2

(vii) 3>4>2>1

Q.28 (a) 3>1>2; (b) 1>2>3; (c) 2>3>1

Q.29

(a) 2; (b) 2; (c) 1; (d) 1; (e) 1

Q.30

(a) 2; (b) 2; (c) 2

Q.31

(a) 1; (b) 2; (c) 2; (d) 1

Q.32

4.25, 1.34×10 5

Q.49

(a) 2; (b) 2; (c) 1; (d) 1; (e) 1

Q.50

(a)2; (b) 2; (c) 2; (d) 2; (e) 1

Q.51

(a) 2; (b) 2; (c) 1; (d) 2; (e) 1

Q.52

(a) 2; (b) 1; (c) 1; (d) 1

Q.53

(a) 1; (b)1; (c) 2; (d)1; (e) 2

Q.54

(a) 1; (b) 1; (c) 2; (d) 1; (e) 2

Q.55

(a) 1; (b) 1; (c) 1; (d) 1

Q.56

(a) 2; (b) 2; (c) 2; (d) 1; (e) 2

Q.57

a, b, c, d, e

Q.58

a, c, d

Q.59 b Q.60 b Q.68 (a) 2>1>4>3; (b) 3>2>1; (c) 3>2>1; (d) 3>1>2; (e) 3>1>2 Q.69 (a) 3>1>2; (b) 4>2>1>3; (c) 4>3>1>2; (d) 1>3>4>2; (e) 3>2>4>1 Q.72 3>1>2

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