Goc-II Ex e Siamrpn

General Organic Chemistry-II
 Marked questions are recommended for Revision.
PART - I : SUBJECTIVE QUESTIONS

Section (A) : Basic strength
A-1. Compare the basic strength of the following compounds:
C2H5O– C2H5– C2H5NH– NH2– F–
(I) (II) (III) (IV) (V)
A-2. Compare the basic strength of the following compounds :

(a) PhNH2 Ph2NH Ph3N
(b)


N N
–
:NH2 H–
(c) Ph–CH2–CH2–NH2
A-3. Which of the following group is most basic in the given compounds :
A-4. Which of the following is a stronger base ? Give reason to justify your answer.
Section (B) : Acidic strength

B-1. Which ‘H’ atom is most acidic in the following compounds.
(I) (II) (III)
B-2. Arrange the following in decreasing order of acidity
B-3. The given compound X = is a strong acid. Justify this statement.
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ADVGOC-II - 12
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Section (C) : Feasible reactions of acids and bases
C-1. Which of the follwing reactions is/are feasible ?
(a) CH3COOH + HCOONa  (b) HCC–Na + H2O 
(c) +  (d) + 
C-2. Which of the following reaction is feasible?

(a) 
H

 (b) +  NH3 + 
(c) +  +

N H2 CH 2 NH C H2
|| || || || 
(d) NH 2  C  NH 2 + CH 3  C  NH 2  NH 2  C  NH 2 + C H3  C  N H3
C-3. Which of the following acids (given below) react with NaHCO 3 and liberate CO2(g) ?
CCl3–COOH CH3–CH2–OH HCl
Section (D) : Tautomerism

D-1. Which of the following compounds can exhibit tautomerism ?
CH3
– –
(A) CH3 – C – C – H (B) Ph – C – CH3 (C) (D)

CH3 O O
O O
O
(E) (F) (G) (H)
O
D-2. Write the tautomers of the following compounds :
(P) (Q) CH3–CH=NH (R) (S)
D-3. Monocarbonyl compounds have very small percentage enol form at equilibrium. Explain.
ADVGOC-II - 13
PART - II : ONLY ONE OPTION CORRECT TYPE
Section (A) : Basic strength
A-1. The correct basic strength order of following anions is :
(A) > > > > >
(B) > > > > >
(C) > > > > >
(D) > > > > >
A-2. Which of the following shows the correct order of decreasing basicity in gas phase ?
(A) (CH3)3N > (CH3)2NH > CH3NH2 > NH3 (B) (CH3)2NH > (CH3)3N > CH3NH2 > NH3
(C) (CH3)2NH > CH3NH2 > (CH3)3N > NH3 (D) (CH3)2NH > CH3NH2 > NH3 > (CH3)3N
A-3. Find the order of basic strength. (If R = Me) ?

(I) R4 N+OH¯ (II) R3N (III) R2NH (IV) RNH2
(A) I > III > IV > II (B) IV > III > I > II (C) II > IV > III > I (D) II > IV > I > III
A-4. Which of the following cannot be a base?
(A) (B) C H3  C  N H2 (C) (D)

||
O
A-5. Select the basic strength order of following molecules ?
(I) Piperidine (II) Pyridine (III) Morpholine (IV) Pyrrole

(A) (IV) > (I) > (III) > (IV) (B) (III) > (I) > (IV) > (II)
(C) (II) > (I) > (III) > (IV) (D) (I) > (III) > (II) > (IV)
A-6. Arrange the following in increasing order of pKa value ?
(I) (II) (III)
(A) II < I < III (B) III < I < II (C) III < II < I (D) II < III < I
A-7. Select the decreasing order of relative basic strengths of following species :
(I) (II) (III) (IV)
(A) II > IV > I > III (B) III > I > IV > II (C) III > IV > I > II (D) II > I > IV > III
ADVGOC-II - 14
A-8. Select the basic strength order of following molecule :
(A) II > III > IV > I (B) II > IV > III > I (C) IV > II > III > I (D) IV > III > I > II
Section (B) : Acidic strength

B-1. Among the following compounds, the strongest acid is :
(A) HC  CH (B) C6H6 (C) C2H6 (D) CH3OH
B-2. Which of the following is not correct decreasing Ka order.

(A) CH4 > NH3 > H2O > HF (B) CH3–OH > CH3–NH2 > CH3–F > CH3–CH3
(C) HI > HBr > HCl > HF (D) PhOH > H2O > C2H5OH > CH3–CCH
B-3. Which of the following acid has the smallest dissociation constant ?
(A) (B) O2N–CH2–CH2–COOH
(C) Cl–CH2–CH2–COOH (D) NC–CH2–CH2–COOH
B-4. Find the strongest acid among the following compounds is :

(A) HOOC–(CH2)2–COOH (B) H3N–(CH2)2–COOH
(C) F–(CH2)2–COOH (D) CH3–(CH2)2–COOH
B-5. Which of the following option shows the correct order of decreasing acidity :
(A) PhCO2H > PhSO3H > PhCH2OH > PhOH (B) PhSO3H > PhOH > PhCH2OH > PhCO2H
(C) PhCO2H > PhOH > PhCH2OH > PhSO3H (D) PhSO3H > PhCO2H > PhOH > PhCH2OH
B-6. Arrange increasing order of acidic strength of following dibasic acids :

(I) oxalic acid, (II) succinic acid, (III) malonic acid, (IV) adipic acid
(A) III < II < I < IV (B) II < III > I > IV (C) I > III > II > IV (D) II > I > III < IV
B-7.
I II III
Arrange above phenol in increasing order of pKa value :
(A) I < II < III (B) III < I < II (C) III < II < I (D) I < III < II
B-8. Order of Ka of following acids is :
O O O
C C – OH
OH C – OH
O2N CH3O
I II III
(A) I > II > III (B) II > I > III (C) I > III > II (D) III > I > II
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B-9. Arrange the following compounds in increasing order of their acidic strength.
(A) IV < II < I < III (B) I < II < III < IV (C) IV < II < III < I (D) I < III < II < IV
B-10. Find the order of Ka of following compounds :
COOH COOH
COOH COOH
(I) (II) (III) (IV) (V) NO2

NO2
NO 2
(A) I < II < III < IV < V (B) IV < I < III < II < V (C) III < II < I < IV < V (D) II < I < III < IV < V
Section (C) : Feasible reactions of acids and bases
1 Mole of CH COONa
C-1. 
3
 ; The products will be :
(A) + CH3COOH (B) + CH3COOH
(C) + CH3COOH (D) Reaction is not feasible
C-2. Which of the following reactions is not feasible ?

COONa
(A) + NaHCO3  + H2O + CO2
(B) + NaHCO3  + H2O + CO2
(C) + NaHCO3  + H2O + CO2
(D) +  +
ADVGOC-II - 16
C-3. Which of the following will accept H+ from NH4+ ion.
(A) (B) (C) (D) CH3–CH2–NH2
2 Mole
C-4. Product
NaHCO3
(A) (B)
(C) (D)
Section (D) : Tautomerism

D-1. Keto-enol tautomerism does not observe in :
(A) (B)
(C) (D)
D-2. The enolic form of acetone contains :
(A) 9  bonds, 1  bond and 2 lone pairs (B) 8  bond, 2  bond and 2 lone pairs
(C) 10  bond, 1  bond and 1 lone pair (D) 9  bond, 2  bond and 1 lone pair
D-3. Molecule can be enolised by which hydrogen ?
(A) y–H (B) z–H (C) both (D) None of these

D-4. Which among the following compound will give maximum enol content in solution :
O O
(A) (B) CH3 – C – CH2 – C – CH3
O O
(C) CH3 – C – CH2 – CH2 – CH3 (D) CH3 – C – CH2 – COOC2H5
D-5. Arrange the following in decreasing order of percentage enol content.
(i) (ii) (iii) (iv)
(A) I > II > III > IV (B) II > I > III > IV (C) II > III > I > IV (D) III > II > IV > I
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PART - III : MATCH THE COLUMN
1. Match the column %
Column-I (Keto) Column-II (% enol)
(A) CH3 – CH = O (x) 95 %
(B) (y) 76 %
(C) (z) 0.0001 %
(D) (w) 7.2 %
2. Match the column :

Column-I Column-II
(A) NaHCO3 will react with (p)
(B) Na will react with (q)
(C) NaOH will react with (r)
(D) NaNH2 will react with (s)
 Marked questions are recommended for Revision.
PART - I : ONLY ONE OPTION CORRECT TYPE

1. Correct basic strength order is :
NH2 NH2 NH – Et NH2
Et NO2
p q r s
(A) r > q > p > s (B) r > p > q > s (C) q > r > p > s (D) r > q > s > p
2. The order of basic strength of the given basic nitrogen atoms is :
(A) III > II > I > IV (B) III > I > II > IV (C) I > III > II > IV (D) II > III > I > IV
ADVGOC-II - 18
3. In the labelled N-atoms which is correct basic strength order :
(A) 2 > 1 > 3 (B) 3 > 1 > 2 (C) 2 > 3 > 1 (D) All are equally basic
4. Choose the strongest base among the following :
(A) (B) (C) (D)
5. Select the basic strength order of following molecules ?
(A) III > II > I (B) II > III > I (C) I > III > II (D) III > I > II
6. Which is the weakest base among the followings ?
(A) (B) (C) (D)
7. Write the order of Ka1 values of following acids :
(I) (II) (III)

(A) II > III > I (B) I > III > II (C) III > II > I (D) II > I > III
8. The acid strength order is :
(A) I > IV > II > III (B) III > I > II > IV (C) II > III > I > IV (D) I > III > II > IV
9. (X) (C6H3ClBrCOOH) are a dihalosubstituted benzoic acids. The strongest acid among all isomers is -
(A) (B) (C) (D)
ADVGOC-II - 19
10. The order of acidity of the H-atoms underlined in the following compounds is in the order :
(I) (II) (III) (IV)
(A) IV>II>I>III (B) II>IV>III>I (C) III>IV>I>II (D) I>III>II>IV

11. Most acidic hydrogen is present in :
(A) (B) (C) (CH3CO)3CH (D) (CH3)3COH
12. The correct orders are :
(A) > Acid strength
(B) > Acid strength
(C) > Basic strength
(D) > Boiling point
13. Observe the following sequence of reactions :
+ CH3NH2 

(1) + + CH3NH2 +
Select the correct option regarding the relative basic strength (Kb) :
(A) > C H3  C  N H2 (B) > CH CNH

3 2
|| ||
NH NH
(C) C H3  C  N H2 > CH3NH2 (D) CH3NH2 >
||
NH
ADVGOC-II - 20
14. Order of Ka which can be predicted by following reaction is :
(A) NH3 > Ph3CH > C2H2 > H2O (B) H2O > HCCH > Ph3CH > NH3
(C) HCCH > H2O > Ph3CH > NH3 (D) Ph3CH > HCCH > H2O > NH3
15. The gases produced in the following reactions are respectively
I : CH3NH2 + NH4Br 
II : CH3SO3H + NaHCO3 
CH3  C  NH2
III : ||
+ NaH 
O
(A) NH3, NH3, CO2 (B) NH3, SO2, H2 (C) NH3, SO2, NH3 (D) NH3, CO2, H2
16. Decreasing order of enol content of the following compounds in liquid phase
(A) 2 > 1 > 3 > 4 (B) 1 > 2 > 3 > 4 (C) 4 > 3 > 2 > 1 (D) 3 > 1 > 2 > 4
PART - II : SINGLE AND DOUBLE VALUE INTEGER TYPE

1. Consider following compound, which H-atom deprotonated first ?
2. How many of the following are correct orders for Basic Strength :
S1 : > CH3–NH2 >
S2 : > > C2H5–NH2
S3 : > >
S4 : > >
S5 : > > C2H5–NH2
ADVGOC-II - 21
3. How many following compounds are more basic than aniline.
CH3–CH2= NH
4. How many of the following compounds give CO2 on reaction with NaHCO3.
, HCl, , , ,
, HCOOH, C2H5–OH, CH3COOH,
5. How many of the following are more acidic than HCOOH.

–
(i) CH2 – COOH (ii) CH3–COOH (iii) OOC – CH2 – COOH (iv) NC–CH2–COOH
|
Cl
(v) CH2 – COOH (vi) CH2 – COOH (vii) CH2 – COOH (viii) CH2 – COOH
| | | |
F NO2 NH– NH3
6. How many of the following compound have less pKa than benzoic acid :
(i) HCOOH (ii) CH3COOH (iii) (iv)
COOH COOH
(v) (vi) (vii) (viii)

NO2
OCH3
7. 90 g of acetic acid react with excess of NaHCO 3 then what volume of CO2 will produce at S.T.P. Write
your answer in terms of nearest integer.
8. In how many of the following pairs first will have higher enol content than second.
COCH3
(i) CH2 &
COOEt
ADVGOC-II - 22
(ii) &
(iii) &
(iv) &
(v) &
9. Consider the following compound and write number of enolizable H-atom
PART - III : ONE OR MORE THAN ONE OPTIONS CORRECT TYPE

1. Which of the following is/are correct for basic strength :
(A) (CH3)2NH > (CH3)3N > CH3NH2 > NH3
(B) (C2H5)2NH > (C2H5)3N > C2H5NH2 > NH3
(C) PhNH2 > Ph2NH > Ph3N
(D) > >
2.
Among the following which statement(s) is/are correct :

(A) Both N of pyrimidine are same basic strength
(B) In imidazole protonation take places on N-3.
(C) In purine only one lone pair of N is delocalised.
(D) Pyrimidine, imidazole and purine all are aromatic.
3. Consider the following compounds
O O O O
|| || || ||
O2N – CH2 – C – OH F – CH2 – C – OH Ph – CH2 – C – OH CH3 – CH2 – C – OH
( I) (II) ( III) ( IV )
Which statement is/are correct :
(A) I > II > III > IV (Acidic strength order)
(B) I is most acidic because of –M effect of –NO2 group
(C) I is most acidic because of –I effect of –NO2 group
(D) IV is least acidic because of +I Effect.
ADVGOC-II - 23
4. Carbolic acid is less acidic than :
(A) CH3COOH (B)
(C) (D)
5.
OHb
Observe the compound and choose correct statement :
(A) It has carboxylic acid group (B) It is Ascorbic acid
(C) Hb is most acidic Hydrogen atom (D) Ha is least acidic Hydrogen atom
6. Which of the following reactions favour backward direction?
(A) + +
(B) + +
(C) + +
(D)
7. The correct statement(s) concerning the structures P, Q, R & S is/are
(P) (Q)
(R) (S)
(A) Q & S are not resonating structures (B) R & S are resonating structures
(C) P & R are tautomers (D) P & Q are resonating structures
ADVGOC-II - 24
8. Among the given pairs, in which pair second compound has less enol content :
O
||
(A) and CH3 – C – CH3 (B) and
(C) and (D) and
PART - IV : COMPREHENSION
Read the following passage carefully and answer the questions.
Comprehension # 1
Ortho effect is a special type of effect that is shown by o-substituents. This ortho-effect operates at the
benzoic acids irrespective of the polar type. Nearly all o-substituted benzoic acid are stronger than
benzoic acid. Benzoic acid is a resonance stabilised and so the carboxyl group is coplanar with the ring.
An o-substituent tends to prevent this coplanarity.
1. What is the order of Ka of following compounds ?
COOH COOH COOH COOH COOH
NO2 Br Cl F OCH3
  IV V
(A) I > II > III > IV > V (B) II > I > III > IV > V (C) V > IV > III > I > II (D) III > II > I > V > IV
2. Which among the following will be the strongest acid ?
(I) (II) (III) (IV)
(A) I (B) II (C) III (D) IV

3. Which of the following is/are correct pKa order ?
(A) > > >
(B) CH3–COOH > > >
(C) > > >
(D) > > >
ADVGOC-II - 25
Comprehension # 2
The lone pair of amines makes them basic. They react with acids to form acid-base salts. Amines are
more basic than alcohols, ethers and water. When an amine is dissolved in water, an equilibrium is
established, where water acts as an acid and transfer a proton to the amine. The basic strength of an
amine can be measured by basicity constant Kb.
Arylamines are less basic than alkylamines because the lone pair of nitrogen is delocalised with the
aromatic ring and are less available for donation.
Substituted arylamines can be either more basic or less basic than aniline, depending on the
substitutent. ERG substituents, such as –CH3, –NH2 and –OCH3 increases the basicity and EWG
substituents, such as –Cl, –NO2 and –CN decreases basicity. While sp2-hybridized nitrogen atom in
pyridine is less basic than the sp3-hybridized nitrogen in an alkylamine.
4. Select the correct order of Kb.
(A) CH3NH2 > NaOH
(B) Pyridine >
(C) p-Methyl aniline > p-Chloroaniline > p-Amino acetophenone
(D) p-Bromoaniline > p-Nitroaniline > p-Amino benzaldehyde
5. pKb order of the following compound is :
(I) NH2OH (II) NH2NH2 (III) NH3 (IV) H2O
(A) IV > I > II > III (B) III > II > I > IV (C) I > IV > II > III (D) III > I > II > IV
6. The most basic carbanion is :
CH2
 
(A) (B) CHC (C) (D)
Comprehension # 3
Observe the following reaction and answer the following questions :
7. The product ‘R’ is :

(A) (B)
(C) (D)
8. The structure of Q1 is :
(A) (B)
(C) (D)
Comprehension # 4
Answer 9, 10 and 11 by appropriately matching the information given in the three columns of the
following table.
Column-1, 2 & 3 containing starting material, reaction condition & electronic effect / intermediate respectively.
Column-1 Column-2 Column-3
Cl
(I) (i) SbCl5 or AlCl3(Anhy.) (P) Rearrangement
ADVGOC-II - 26
Cl
(II) (ii) Na (Q) Resonance

(III) N (iii) H+ (R) Hyperconjugation
|
H H
Cl
(IV) (iv) NaOH (S) Carbocation intermediate
9. Which combination will give hydrogen gas ?

(A) (IIl) (iii) (P) (B) (ll) (ii) (R) (C) (lV) (ii) (Q) (D) (l) (iii) (P)
10. In which product formation is not possible ?

(A) (l) (ii) (Q) (B) (ll) (i) (R) (C) (lll) (ii) (Q) (D) (lV) (i) (S)
11. In which amongs the following aromatic product will not form ?
(A) (l) (i) (P) (B) (ll) (i) (Q) (C) (lll) (iv) (Q) (D) (lV) (ii) (Q)
* Marked Questions may have more than one correct option.

PART - I : JEE (ADVANCED) / IIT-JEE PROBLEMS (PREVIOUS YEARS)
1. Which of the following acid has the lowest value of acid dissociation constant : [JEE-02(S), 3/90]
(A) CH3CHFCOOH (B) FCH2CH2COOH (C) BrCH2CH2COOH (D) CH3CHBrCOOH
2. Match the Ka values : [JEE-03(M), 2/60]
Compounds Ka
(a) Benzoic acid (i) 3.3 × 10–5
(b) (ii) 6.3 × 10–5
(d) (iii) 30.6 × 10–5
(e) (iv) 6.4 × 10–5
(f) (v) 4.2 × 10–5
3. Compound A of molecular formula C9H7O2Cl exists in keto form and predominantly in enolic form ‘B’.
On oxidation with KMnO4’A’ gives m-Chlorobenzoic acid. Identify ‘A’ and ‘B’. [JEE(M)-03]
4. A. The product A will be - [JEE-03(S), 3/84]
ADVGOC-II - 27
(A) (B)
(C) (D)
5. What is the acidity order of x, y & z ? [JEE-04(S), 3/84]
(A) x > y > z (B) x > z > y (C) y > z > x (D) z > y > x
6. Which one of the following two compounds is the stronger acid? Explain why? [JEE 2004, 4/60]
Excess of CH COONa
7.      
3
   [JEE-05(S), 3/84]
The products will be :

(A) + CH3COONa
(B) + CH3COOH
(C) + CH3COOH
(D) + SO3
NaHCO NaHCO
8. 
3
; 
3

Benzenesulphonic acid and para nitrophenol react with NaHCO3 separately. The gases produced are
respectively. [JEE-06, 3/184]
(A) SO2, CO2 (B) SO2, CO (C) SO2, NO2 (D) CO2, CO2
ADVGOC-II - 28
9. The correct acidity order of the following is : [JEE-09, 3/160]
(A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II)
(C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I)
10. The total number of basic groups in the following form of lysine is : [JEE-10, 3/163]
11. Among the following compounds, the most acidic is : [JEE-11, 3/180]
(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p-toluic acid
12. The compound that does NOT liberate CO2, on treatment with aqueous sodium bicarbonate solution, is:
[JEE(Advanced) 2013, 2/120]
(A) Benzoic acid (B) Benzenesulphonic acid
(C) Salicylic acid (D) Carbolic acid (Phenol)
13. The correct order of acidity for the following compounds is [JEE(Advanced) 2016, 3/124]
CO2H
CO2H CO2H CO2H

HO OH OH
OH
OH
I II III IV
(A) I > II > III > IV (B) III > I > II > IV (C) III > IV > II > I (D) I > III > IV > II
14. The order of basicity among the following compounds is [JEE(Advanced) 2017, 3/122]
NH NH2
N NH HN N
H3C NH2 H2N NH
(I) (II) (III) (IV)
(A) II > I > IV > III (B) I > IV > III > II (C) IV > II > III > I (D) IV > I > II > III
PART - II : JEE (MAIN) / AIEEE ONLINE PROBLEMS (PREVIOUS YEARS)

1. Which one of the following statements is not correct ? [JEE(Main) 2014 Online (11-04-14), 4/120]
(1) Alcohols are weaker acids than water.
(2) Acid strength of alcohols decreases in the following order RCH 2OH > R2CHOH > R3COH.
(3) Carbon-oxygen bond length in methanol, CH3OH is shorter than that of C–O bond length in phenol.
O
(4) The bond angle C in methanol is 108.9º.
H
2. Which one of the following compounds will not be soluble in sodium bicarbonate ?
[JEE(Main) 2014 Online (19-04-14), 4/120]
(1) 2,4,6-Trinitrophenol (2) Benzoic acid
(3) o-Nitrophenol (4) Benzene sulphonic acid
ADVGOC-II - 29
3. Arrange the following amines in the order of increasing basicity :
[JEE(Main) 2015 Online (10-04-15), 4/120]
NH2 NH2 NH2 NH2 NH2 NH2
(1) CH3NH2 < < < (2) < < < CH3NH2
OCH3 NO2 OCH3 NO2

NH2 NH2 NH2 NH2 NH2 NH2
(3) < < < CH3NH2 (4) < < < CH3NH2
OCH3 NO2 NO2 OCH3
4. The "N" which does not contribute to the basicity for the compound is :
[JEE(Main) 2016 Online (10-04-16), 4/120]
6 7
5 N
1N
8
2 N 4 N9
3 H
(1) N 7 (2) N 1 (3) N 9 (4) N 3
5. Among the following compounds, the increasing order of their basic strength is :
[JEE(Main) 2017 Online (09-04-17), 4/120]
NH2
(I) (II)
N
H
N CH 3
(III) (IV)
NH2
(1) (I) < (II) < (III) < (IV) (2) (I) < (II) < (IV) < (III)
(3) (II) < (I) < (III) < (IV) (4) (II) < (I) < (IV) < (III)
6. The increasing order of the acidity of the following carboxylic acids is :

[JEE(Main) 2018 Online (15-04-18), 4/120]
CO2H CO2H CO2H CO2H
NO2 OH Cl
I II III IV
(1) I < III < II < IV (2) IV < II < III < I (3) II < IV < III < I (4) III < II < IV < I
7. Which amongst the following is the strongest acid ? [JEE(Main) 2019 Online (09-01-19), 4/120]
(1) CHBr3 (2) CHCl3 (3) CHI3 (4) CH(CN)3
8. The correct decreasing order for acid strength is : [JEE(Main) 2019 Online (09-01-19), 4/120]
(1) CNCH2COOH > O2NCH2COOH > FCH2COOH > ClCH2COOH
(2) FCH2COOH > NCCH2COOH > NO2CH2COOH > ClCH2COOH
(3) NO2CH2COOH > NCCH2COOH > FCH2COOH > ClCH2COOH
(4) NO2CH2COOH > FCH2COOH > CNCH2COOH > ClCH2COOH
ADVGOC-II - 30
9. Arrange the following amines in the decreasing order of basicity :
[JEE(Main) 2019 Online (09-01-19), 4/120]
N N N
| |
H H
(I) (II) (III)
(1) I > III > II (2) III > I > II (3) III > II > I (4) I > II > III
10. The increasing basicity order of the following compounds is:
[JEE(Main) 2019 Online (09-01-19), 4/120]
CH2CH3 CH3 CH3
(A) CH3CH2NH2 (B) CH3CH2NH (C) H3C–N–CH3 (D) Ph–N–H
(1) (A) < (B) < (C) < (D) (2) (D) < (C) < (B) < (A)
(3) (A) < (B) < (D) < (C) (4) (D) < (C) < (A) < (B)
11. The increasing order of the pKa values of the following compounds is :
[JEE(Main) 2019 Online (10-01-19), 4/120]
OH OH OH OH
NO2
NO2 OMe
A B C D
(1) C < B < A < D (2) B < C < D < A (3) B < C < A < D (4) D < A < C < B
12. In the following compound the favourable site/s for protonation is /are :
[JEE(Main) 2019 Online (11-01-19), 4/120]
(1) (a) and (e) (2) (a) and (d) (3) (b), (c) and (d) (4) (a)
13. The correct order of acid strength of compounds CHCH, CH3–CCH and CH2=CH2 is as follows :
[JEE(Main) 2019 Online (12-01-19), 4/120]
(1) CH3–CCH > CHCH > CH2=CH2 (2) CH3–CCH > CH2=CH2 > HCCH
(3) HCCH > CH3–CCH > CH2= CH2 (4) CHCH > CH2=CH2 > CH3–CCH
ADVGOC-II - 31
EXERCISE - 1
PART - I
A-1. II > III > IV > I > V
A-2. (a) PhNH2 > Ph2NH > Ph3N
(b) > >



N N
–
–
:NH2 H
(c) Ph–CH2–CH2–NH2 > >
A-3. 2
A-4. I is less basic than II because, in compound (I) the lone pair of electrons is involved in resonance but
not in II.
B-1. I - a, II - b, III - c, (acidic strength  stability of conjugate base)
B-2. III > I > II (acidic strength  stability of conjugate base) In III conjugate base is highly stabilised by intra
molecular H-bonding.

H
B-3.     etc.
Its conjugate base (anion) is resonance stabilised like RCOO anion of carboxylic acid.
C-1. (a) Not feasible (b) Feasible (c) Not feasible (d) Not feasible
C-2. (c) Strong base accept H+ ions so this reaction is feasible.
C-3. (i, iii, iv, v, vi, vii)
D-1. B, C, E, G, H can show tautomerism.
OH
|
D-2. (P) CH3  C  CH2 (Q) CH2=CH–NH2 (R) (S)
D-3. In Monocarbonyl Keto form is more stable due to greater strength of the carbon-oxygen double bond as
compared to the carbon carbon double bond.
PART - II
A-1. (C) A-2. (A) A-3. (A) A-4. (D) A-5. (D)
A-6. (A) A-7. (D) A-8. (D) B-1. (D) B-2. (A)
B-3. (C) B-4. (B) B-5. (D) B-6. (C) B-7. (C)
B-8. (C) B-9. (A) B-10. (D) C-1. (B) C-2. (C)
C-3. (D) C-4. (C) D-1. (A) D-2. (A) D-3. (B)
D-4. (A) D-5. (A)
PART - III
1. (A - z) ; (B - x) ; (C - w) ; (D - y) 2. (A - p,q,s) ; (B - p,q,r,s) ; (C - p,q,r,s) ; (D - p,q,r,s)
ADVGOC-II - 32
EXERCISE - 2
PART - I
1. (B) 2. (D) 3. (A) 4. (D) 5. (A)
6. (D) 7. (A) 8. (D) 9. (B) 10. (A)
11. (C) 12. (A) 13. (C) 14. (B) 15. (D)
15. (B)
PART - II
1. 2 2. 4 (S1, S2, S4, S5) 3. 5 (ii, iii, iv, vi, vii)
4. 6 (i, ii, iii, vi, vii, ix) 5. 5 (i, iv, v, vi, viii) 6. 5 (i, iv, v, vi, viii)
7. 34 8. 3 9. 10
PART - III
1. (BCD) 2. (ABCD) 3. (ACD) 4. (ACD) 5. (BC)
6. (BD) 7. (ABCD) 8. (ACD)
PART - IV
1. (A) 2. (C) 3. (B) 4. (C) 5. (A)
6. (D) 7. (D) 8. (C) 9. (C) 10. (D)
11. (A)
EXERCISE - 3
PART - I
1. (C) 2. (a) – (ii) ; (b) – (iii) ; (c) – (iv) ; (d) – (i) ; (e) – (v)
3. A. ; B. 4. (A) 5. (A) 6.
7. (B) 8. (D) 9. (A) 10. 2 11. (C)

12. (D) 13. (A) 14. (D)
PART - II
1. (3) 2. (3) 3. (4) 4. (3) 5. (4)
6. (4) 7. (4) 8. (3) 9. (2) 10. (4)
11. (3) 12. (3) 13. (3)
ADVGOC-II - 33

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General Organic Chemistry-II

 Marked questions are recommended for Revision.

PART - I : SUBJECTIVE QUESTIONS

A-2. Compare the basic strength of the following compounds :

Section (B) : Acidic strength

(I) (II) (III)

B-2. Arrange the following in decreasing order of acidity

B-3. The given compound X = is a strong acid. Justify this statement.

(c) +  (d) + 

C-2. Which of the following reaction is feasible?

CCl3–COOH CH3–CH2–OH HCl

Section (D) : Tautomerism

(A) CH3 – C – C – H (B) Ph – C – CH3 (C) (D)

D-2. Write the tautomers of the following compounds :

(P) (Q) CH3–CH=NH (R) (S)

(A) > > > > >

(B) > > > > >

(C) > > > > >

(D) > > > > >

A-3. Find the order of basic strength. (If R = Me) ?

A-4. Which of the following cannot be a base?

(A) (B) C H3  C  N H2 (C) (D)

(I) Piperidine (II) Pyridine (III) Morpholine (IV) Pyrrole

A-6. Arrange the following in increasing order of pKa value ?

(I) (II) (III)

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

Section (B) : Acidic strength

B-2. Which of the following is not correct decreasing Ka order.

(C) Cl–CH2–CH2–COOH (D) NC–CH2–CH2–COOH

B-4. Find the strongest acid among the following compounds is :

B-6. Arrange increasing order of acidic strength of following dibasic acids :

(I) (II) (III) (IV) (V) NO2

(A) + CH3COOH (B) + CH3COOH

(C) + CH3COOH (D) Reaction is not feasible

C-2. Which of the following reactions is not feasible ?

(A) + NaHCO3  + H2O + CO2

(B) + NaHCO3  + H2O + CO2

(C) + NaHCO3  + H2O + CO2

(A) (B) (C) (D) CH3–CH2–NH2

Section (D) : Tautomerism

D-3. Molecule can be enolised by which hydrogen ?

(A) y–H (B) z–H (C) both (D) None of these

(i) (ii) (iii) (iv)

(C) (z) 0.0001 %

(D) (w) 7.2 %

2. Match the column :

(A) NaHCO3 will react with (p)

(B) Na will react with (q)

(C) NaOH will react with (r)

(D) NaNH2 will react with (s)

 Marked questions are recommended for Revision.

PART - I : ONLY ONE OPTION CORRECT TYPE

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

5. Select the basic strength order of following molecules ?

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

7. Write the order of Ka1 values of following acids :

(I) (II) (III)

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

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