Varun JEE Advanced 2024

ALCOHOL, PHENOL & ETHER DPP-01

1. Match the column:

Column-I Column-II
(A)  (P) No reaction
O ⎯⎯⎯
H3O
→

(B) CH3 (Q) CH3

H3O
CH3 – C – O – CH – CH 3 ⎯⎯⎯→ CH3 – C – OH is one of the product of the reaction

CH3 CH3 CH3

(C) CH3 (R) OH
H3O
CH3 ⎯⎯⎯
O C → is one of the product of the reaction
CH3
(D) CH3 (S) CH3 – CH – OH is one of the product of the reaction

O CH ⎯⎯⎯
H3O
→ CH3
CH3

2. Match the column:

Column-I Column-II
(Compound)
(A) (P) Gives orange colour Brady’s reagent (2, 4-DNP)

O
(B) (Q) Gives haloform reaction

Cl
(C) O (R) Gives positive Beilstein test

(D) Cl (S) Can give aldol reaction with dil. NaOH

(T) Gives white ppt. with alcoholic AgNO3

3. Match the column:

Column-I and column-II contains four entries each. Entry of column-I are to be uniquely matched with only
one entry of column-II.

Column-I Column-II
(Compound) (Boiling point in °C)
(A) H3C – CH2 – CH2 – CH2 – CH2 – OH (P) 290°C
(B) H3C – CH – CH3 (Q) 138°C
OH
(C) H2C CH CH2 (R) 102°C
OH OH OH
(D) CH3 (S) 82.4°C
H3C C CH2 CH3
OH
4. Match the column:
Column-I Column-II
(organic compounds oxidised by HIO4) (Products of HIO4 oxidation)
(A) CH3CH2CH CH CH2CH3 ⎯⎯⎯ HIO4
→ (P) 2H2C = O + HCOOH
OH OH
(B) PhCH2CH CH CH3 ⎯⎯⎯
HIO4
→ (Q) 2CH3CH2CH = O
OH OH
(C) CH2 CH2 ⎯⎯⎯
HIO4
→ (R) 2H2C = O
OH OH
(D) CH2 CH2 CH2 ⎯⎯⎯
HIO4
→ (S) PhCH2CH = O + CH3CH = O
OH OH OH

5. Match the column:

Column-I Column-II
(A) MnSO4 + Na2BiO3 + H+ (P) Purple colour
(B) − (Q) Red colour
Fe3+ + 3SC N ⎯⎯
→
(C) C2 H5 − OH ⎯⎯⎯⎯⎯⎯
Cerric Ammonium
Nitrate
→ (R) Prussian blue

(D) (S) Black ppt.

⎯⎯
Na

→ ⎯⎯⎯⎯
FeSO4
NaOH/ 
→ ⎯⎯⎯⎯
FeCl3
conc. HCl
→ colour
N
H

6. Match the column:

Column-I Column-II
(A) C C C (P) Major product decolourize Br2 – H2O

C C N C + OH–

C C
(B) MeONa + Me3C – Cl ⎯→ (Q) Ozonolysis of major product gives a product which
Will give positive iodoform test.
(C) C C (R) Carbocation is formed as intermediate during this
C ⎯⎯⎯⎯⎯ →
conc.H SO
2 4
C C C C  reaction.
C OH
(S) Isobutene is obtained as major product.

7. Match the column

Column-I Column-II
(Reaction) (Major product)
(A) H+ /H2O
(P)
⎯⎯⎯⎯ → OH

(B) (Q)
⎯⎯⎯⎯⎯⎯→
(i)Hg(OAc)2 /H2O
(ii)NaBH /OH− OH
4

(C) (R) OH
⎯⎯⎯⎯⎯
(i)BH3 /THF
(ii)H O /OH
→
2 2

(S) OH
8. We want to produce alcohol from the given substrates in Column 'I'. Match the number of CH3MgX required
under Column 'II'.
Column-I Column-II
(A) CH3COOC2H5 (P) 1
(B) CH3COCl (Q) 2
(C) (R) 3

(D) HOCH2COOC2H5 (S) 4


11. Structure of A is
9. ⎯⎯⎯
H3O
excess
→X
O O 
+ ⎯⎯
H
⎯
→A
HO OH
Structure of X is O

OH
(A) (A)
HO HO H O HO O

(B) O OH
OH OH (B)
HO
OH

(C) OH
(C)
O OH OH HO O

(D) O
(D)
HO HO HO OH

10. A & B are respectively:

12. Major product (R) dosen’t shows:
+
⎯⎯⎯ + → A ⎯⎯→
OsO4 H

B OH
H3O

OH OH ⎯⎯⎯
P.C.C
→ (P) HO OH (Q)
(2mole) (1 mole)
(A) & CH2OH

OH ⎯⎯⎯⎯⎯ → (R) ⎯⎯⎯⎯⎯

(i)CH3MgBr

Lucas reagent
→ (S)
(ii)H /H2O
(B) &
OH
(A) Haloform reaction
O
OH
(B) Tollen’s Test
(C) &
OH
(C) Fehling Test
OH OH O

(D) & (D) 2, 4 – DNP Test

13. X is 15. Major product of the following reaction is:
18
OH + OH
OH
 COOH
⎯⎯
H
⎯
→X

⎯⎯⎯⎯⎯
conc.H2SO4
→ P.

(A) C–O

(A) O

O
18
(B) C–O
O
(B) O

(C) C–O
O O

OH 18
(D) C–O
(C) O

16. P and Q are

CH3
(D)
H TsCl NaBr P
OH DMSO

Et PBr 3
Q

(A) Identical
14. Major product of the following reaction is:
(B) Enantiomer

(C) Diastereomer
⎯⎯
BF3
⎯→ (A)
(D) Positional isomer

O 17. Consider following conversion:

||
(A) R − C
(A)
Propan-1-ol P
Propoxy
(B)
Q Propane

(B) A and B are respectively:

(A) Alc. KOH, PCl5

R' O
| ||
R −C− C−H (B) Na metal, SOCl2
(C) |
R (C) conc. H2SO4 / 170°C

(D) HBr, conc. H2SO4

(D)
 ANSWER KEY
1. (A)→P; (B)→Q,S; (C)→Q,R; (D)→R,S 10. (C)
2. (A)→P,Q,S (B)→Q,R,T (C)→P,S (D)→R,T 11. (B)
3. (A)→Q; (B)→S; (C)→P; (D)→R 12. (A)
4. (A)→Q; (B)→S; (C)→R; (D)→P 13. (B)
5. (A)→P; (B)→Q; (C)→Q; (D)→R 14. (A)
15. (B)
6. (A)→PQS; (B)→PQS; (C)→PQR
16. (A)
7. (A)→Q; (B)→R; (C)→S
17. (B)
8. (A)→Q; (B)→Q; (C)→S; (D)→R
9 (B)

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