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Crash Course
JEE Main 2020
EXERCISE SHEET
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Plot No. 46, In front of Skyline Apartments, Corner Building,
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ALCOHOL PHENOL AND ETHER
Ph CH3
CH3 OH
2. Consider the following reaction.
O16
IA
16 +
H
CH3 – C – O18 –C 2H 5 + H 2O
Heat
The products formed in the reaction are
O16 O16
D
(A) CH3 – C – O16 H and C2H5O18H (B) CH3 – C – O18 H and C2H5O16H
O16 O18
3.
(C) CH3 – C – O16 H and C2H5O16H
Consider the following reaction sequence,
N (D) CH3 – C – O18 H and C2H5O18H
SI
O
1.CH 3 MgI POCl 3
A B
2.H 2 O Pyridine,0°C
cold excess
(A) (B)
(C) (D)
The order of reactivity of A, B, C and D towards hydrolysis by SN1 mechanism is :
(A) A < B < C < D (B) D < C < B < A (C) D < A < B < C (D) C < B < A < D
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ALCOHOL PHENOL AND ETHER
6. Propene is allowed to react with m-chloroperoxobenzoic acid. The product (A) is then reduced with LiAlH4 in dry
ether to give (B).
MCPBA 1. LiAlH 4
CH 3 CH = CH 2 A +
B
2. H 3O
Cl dry ether
CH2Br + CH3CHO + Mg H 3O +
A B
IA
the product (B) is :
D
OH OH
9.
OH OH
N
The reaction of 1 mol each of p-hydroxyacetophenone and methyl magnesium iodide will give :
SI
(A) CH4 + IMgO COCH 3 (B) CH3O COCH3
OMgI MgI
O
CH3
O
CH2 C O
(A) RCH CH2 (B) R CH HC R
O C CH2
O C= O
O
(C) RCH = CHCOOH (D) None of these
12. In the reaction of phenol with CHCl3 and aqueous NaOH at 70°C, the electrophile attacking the ring is :
(A) CHCl3 (B) C HCl2
(C) CCl (D) COCl2
2
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ALCOHOL PHENOL AND ETHER
H 3C OCH 3 + HBr
IA
(IV) :
(A) I > IV > III > II (B) IV > III > II > I (C) I > III > II > IV (D) III > II > I > IV
16. The conversion
O OH
D
CH3 C CH2CH2 CO2CH3 CH3 CH CH2CH2 CO2CH3
(A) LiAlH4 and then H+ (B) NaBH4 and then H+
17.
(C) H2/ Carbon
Identify the final product of the reaction :
+
N (D) None of these
SI
H3O
CH3MgBr + CH2 CH2 ?
O
O
(C) HCl > HBr > HI (D) Ethers do not undergo cleavage
19. Consider the following reactions :
ET
dil.KMnO 4 (CH3COO)4Pb
A B
Cold
The product (B) is
OH CH3COO O O
O O
OH CH3COO
20. Decreasing order of relative nucleophilicity of the following nucleophiles in protic solvent is -
, , , ,H2O
(A) > > H2O > > (B) > > > > H2O
(C) > > > H2O > (D) > > > > H2O
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ALCOHOL PHENOL AND ETHER
NO2 Br CH3
22. The correct order of reactivity of following alcohols towards conc.HCl/ZnCl2 is :
Ph OH
OH OH OH
I II III IV
(A) I > II > III > IV (B) I > III > II > IV (C) IV > III > II > I (D) IV > III > I > II
IA
23. Which one of the following will be most reactive for SN1 reaction ?
OH OH OH OH
| | | |
(A) CH (B) C6H5–CH–C6H5 (C) CH3– C– CH3 (D) C
|
D
CH3
24. Which describes the best stereochemical aspects of the following reaction ?
Ph
CH3
OH
Et H–Br
N
Product
SI
(A) Inversion of configuration occurs at the carbon undergoing substitution.
(B) Retention of configuration occurs at the carbon undergoing substitution.
(C) Racemization occurs at the carbon undergoing substitution.
(D) The carbon undergoing substitution is not stereogenic.
O
CH3
25. D HI Product
O
OH
Identify the major product :
CH3
ET
D I
I D
(A) (B) I (C) (D) D
D I
SOCl
2
26. Product
O pyridine, Δ
(X)
CH2OH
Product of the above reaction is :
CH3
PCl
27. H OH
5
X ; (X) is
C2H5
(D-2-Butanol)
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ALCOHOL PHENOL AND ETHER
PBr
3
28. (X) , X is : (X)
H
|
C SOCl2 Product
29. H5C6 OH
CH3
IA
Identify the product
H H H H
| | | |
C C C C
(A) H5C6 Cl (B) Cl C6H5 (C) HS C6H5 (D) H5 C6 SH
D
CH3 CH3 CH3 CH3
30. Consider the following reaction.
OH
|
N SOCl2
CH3 – CH 2 – CH – CH 3
Cl
|
CH3 – CH2 – CH – CH3
SI
ether
In the above reaction which phenomenon will take place :
(A) Inversion (B) Retention (C) Racemisation (D) Isomerisation
O
HCl/Δ
31. In the given reaction : CH3 – CH2 – CH2 – O – CH2 – CH3 [X] + [Y]
[X] and [Y] will respectively be :
O
(A) CH3–CH2 –CH2OH & CH3–CH2 –Cl (B) CH3–CH2–CH2–Cl & CH3–CH2–OH
(C) CH3–CH2–CH2–Cl & CH2=CH2 (D) CH3–CH=CH2 & CH2=CH2
ET
– +
CH3 EtO K /EtOH
X
|
32. CH3 – C – CH2
O +
Y
EtOH/H
The product X and Y are respectively :
CH3 CH3 CH3 CH3
| | | |
(A) CH3 – C – CH2 OCH2CH3 & CH3 – C – CH2OH (B) CH3 – C – CH2OH & CH3 – C – CH2 OCH2CH3
| | | |
OH OCH2CH3 OCH2CH3 OH
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ALCOHOL PHENOL AND ETHER
33. The relative rate of acid catalysed dehydration of following alcohols would be,
CH3 CH3
| |
CH – CH – CH3 CH – CH2 – CH2 – OH
|
OH
I II
CH3 CH3
| |
C – CH2 – CH3 C – CH2OH
| |
OH CH3
III IV
(A) III > I > IV > II (B) III >IV > I > II (C) I > III > IV > II (D) III > IV > I > II
IA
34. H SO 4
2
D
In the above reaction the major product is shown, which is formed through the intermediate (carbocation) given below
(q)
(p) H
(s)
(r)
N
SI
Which bond will migrate to form the above product ?
(A) p (B) q (C) r (D) s
O
Conc. H2SO4
35. Major product is :
O
OH OH
HBr HBr
36. (A) , (B)
Δ Δ
CH2OH OCH3
The product (A) and (B) are respectively :
OH OH OH OH
OH Br Br Br
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ALCOHOL PHENOL AND ETHER
CH(Me)Cl
Ether
SOCl2
37. CH(Me)OH CH(Me)OSOCl (X)
–HCl
[R] C5H5N
CH(Me)Cl
(Y)
Which configuration will be adopted by X and Y respectively :
(A) R, R (B) R, S (C) S, S (D) S, R
38. When (1R, 2R)-1, 2-Dibromo-1, 2-diphenyl ethane is treated with alcoholic solution of KOH, the most probable
product would be :
(A) trans-1, 2-diphenyl ethene (B) A mixture of cis, trans alkenyl bromide
(C) cis-alkenyl bromide (D) trans-alkenyl bromide
IA
CH3
|
H3PO4 Fractional
39. CH3 – CH2 – C – CH – CD3 Total no. of alkenes (X) No. of Fractions obtained (Y)
| | distilation
CH3 OH
D
X and Y are :
(A) 6 ,6 (B) 9, 5 (C) 9, 6 (D) 6, 4
40. Number of fractions on fractional distillation of solvolysis in ethanol of 1-chlorobut-2-ene is :
41.
(A) 1
CH3CH2OH + HCl
ZnCl2
(B) 2
CH3CH2Cl + H2O
N (C) 3 (D) 4
SI
In the above reaction, the leaving group is :
NaOH(aq.)
42. Cl–CH2CH2CH2CH2OH A, the product A is :
O
OH
43. Which of the following reactions is the best choice for preparing methyl cyclohexyl ether ?
44. Which of the following statements are correct for the given alcohol ?
X –
R – OH R – X + OH
– – –
(A) Reaction will not take place because OH is poor leaving group ; X is weak base and OH is strong base
– – –
(B) Reaction will not take place because OH is poor leaving group ; X is strong base and OH is weak base.
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ALCOHOL PHENOL AND ETHER
– – –
(C) Reaction will not take place because OH is strong leaving group ; X is strong base and OH is weak base.
– – –
(D) Reaction will not take place because OH is good leaving group ; X is weak base and OH is strong base.
45. Consider the following reactions carried out at the same temperature.
(I) (II)
IA
CH2OH
TsCl 80°C
46. (A) (B) 84%, final product (B) is :
OH
Pyridine
0°C
D
47.
(A) (B) N (C)
HO Br O CH3 HO OH O
Ph Ph Ph H3 C CH3 CH3
O
+
H NaNO2
(C) CH3–C–C–CH3 Ph–C–C–CH3 (D) CH3–C–C–CH3 CH3 –C–C–CH3
HCl
HO OH O CH3 HO NH2 O CH3
ET
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ALCOHOL PHENOL AND ETHER
1. Among the following compound which can be dehydrated very easily is : [AIEEE-2004]
H3C H3C
(1) (2)
OH H3C OH
CH3
OH
(3) (4)
H3C CH3 H3C CH3
OH
IA
|| -
(A) CH3C – O - (B) CH 3O (C) CN (D) H3C S–O
|| ||
O O
(1) (C), (B), (A), (D) (2) (B), (C), (A), (D) (3) (D), (C), (B), (A) (4) (A), (B), (C), (D)
D
3. (I) 1, 2 - Dihydroxy benzene [IIT-JEE 2006]
(II) 1, 3- Dihydroxy benzene
(III) 1, 4-Dihydroxy benzene
(IV) Hydroxy benzene
N
The increasing order of boiling points of the above mentioned alcohols is -
SI
(1) I < II < III < IV (2) I < II < IV < III (3) IV < I < II < III (4) IV < II < I < III
4. Which one of the following reagents is used in the following reaction ? [JEE 2007]
OH ONa OH
O
CHO CHO
aq. HCl
[1]
Intermediate
O
(1) aq. NaOH + CH3Cl (2) aq. NaOH + CH2Cl2 (3) aq. NaOH + CHCl3 (4) aq. NaOH + CCl4
OH
NaOH(aq.)/Br 2
5. In the reaction the intermediate (s) is / are : [IIT 2010]
O
Br
Br Br Br
Br Br
6. The main product of the following reaction is :
[AIEEE-2010]
conc. H 2SO 4
C6H5CH2CH(OH)CH(CH3)2
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ALCOHOL PHENOL AND ETHER
H5 C6 H C6 H5CH2 CH3
(1) C C (2) C C
H CH(CH3)2 H CH3
C6 H5 CH(CH3)2 H5C 6CH2CH2
(3) C C (4) C CH2
H H H3C
7. From amongst the following alcohols the one that would react fastest with conc. HCl and anhydrous ZnCl2, is
[AIEEE-2010]
(1) 2-Butanol (2) 2-Methylpropan-2-ol (3) 2-Methylpropanol (4) 1-Butanol
8. Consider thiol anion (RS) and alkoxy anion (RO). Which of the following statements is correct ? [AIEEE-2011]
(1) RS is less basic but more nucleophilic than RO.
(2) RS is more basic and more nucleophilic than RO.
(3) RS is more basic but less nucleophilic than RO.
(4) RS is less basic and less nucleophilic than RO.
IA
9. An unknown alcohol is treated with the “Lucas reagent” to determine whether the alcohol is primary, secondary or
tertiary. Which alcohol reacts fastest and by what mechanism : (JEE (Mains) 2013)
(1) secondary alcohol by SN1 (2) tertiary alcohol by SN1
D
(3) secondary alcohol by SN2 (4) tertiary alcohol by SN2
10. The most suitable reagent for the conversion of R – CH2 – OH R – CHO is : [IIT 2014]
(1) CrO3 (2) PCC (Pyridinium Chlorochromate)
11.
(3) KMnO4
The product of the reaction given below is :
N(4) K2Cr2O7
SI
O
O
12. Phenol on treatment with CO2 in the presence of NaOH followed by acidification produces compound X as the major
ET
product. X on treatment with (CH3CO)2 O in the presence of catalytic amount of H2SO4 produces :
(JEE (Mains) 2018)
CO 2H
O
O O
O CH3
O C
CH3
O O CH3
OH
CO2H
(1) (2) (3) (4)
O CH3
CO2H
O
CO2H
13. Phenol reacts with methyl chloroformate in the presence of NaOH to form product A. A reacts with Br2 to form
product B. A and B are respectively : (JEE (Mains) 2018)
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ALCOHOL PHENOL AND ETHER
O O O O
O O O O
O and O
O and O
(1) (2)
Br
Br
OH OH Br
OH OH
and and
(3) OCH3 OCH3 (4) OCH3 OCH3
O O
Br O O
14. The major product of the following reaction is : 16. The major product of the following reaction is :
O
(JEE (Mains) 2019) LiAlH 4
HI ( excess )
CH3 CH = CHCO2 CH 3 ¾¾ ¾¾ ®
¾¾¾¾® D
IA
NC O (1) CH3CH2CH2CHO (JEE (Mains) 2019)
D
NC I NC OH (4) CH3CH2CH2CH2OH
OH I
(3)
NC OH
(4)
NC I
N
SI
15. The major product of the following reaction is: 17. The major product of the following reactions:
O (JEE (Mains) 2019) OCH3 (JEE (Mains) 2019)
Br
O
¾¾¾¾
NaBH 4
®
MeOH,25ºC ¾¾¾¾¾¾
Conc HBr (excess)
heat
®
OH
O
CH=CH2
OMe
OH Br
(1)
ET
(1) (2)
OH
Br CH2CH2Br CH2CH 2Br
(2) Br OH
(3) (4)
OMe
(3)
Br–CHCH3 Br–CHCH 3
O
(4)
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ALCOHOL PHENOL AND ETHER
OH
18. CH3CH2 –C–CH3 cannot be prepared by :
21. The major product of the following reaction is:
Ph (JEE (Mains) 2019) (JEE (Mains) 2019)
O CH3
(1) HCHO + PhCH(CH3)CH2MgX (i) dil. HCl/D
(2) PhCOCH2CH3 + CH3MgX O (ii) (COOH)2/
CH3O OH
Polymerisation
(3) PhCOCH3 + CH3CH2MgX
(4) CH3CH2COCH3 + PhMgX O
O O
(1) n
O
19. The major product of the following reaction OCOCH 3
IA
is :- (JEE (Mains) 2019) O
O O
HO (1)
1) n
(2) O
(2) AlCl3 (Anhyd.)
D
OCH3
Cl HO O
(1) (2) O
N O
n
(3) O
Cl HO
SI
(3) (4) OH
O
O O
Ans. (2) (4) n
O
O
OH
20. Which is the most suitable reagent for the
following transformation ? (JEE (Mains) 2019)
O
OH
CH3–CH=CH–CH2–CH–CH3 ¾¾®
ET
CH3–CH=CH–CH2CO2H
(1) alkaline KMnO4 (2)I
2 2/NaOH
(3)Tollen's
3 reagent (4)CrO
4 2/CS2
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ALCOHOL PHENOL AND ETHER
NO2 NO2
[IIT-2004]
IA
OH
15
4. An organic compound P(C5H10O) reacts 10 times faster than ethylene with dilute H2SO4 to give two products Q and
R. Both Q and R give positive iodoform test. Identify P, Q and R and also give reason for very high reactivity of P.
[IIT-2004]
D
O
OH
1. O3 NaOH
5. (X) (Y)
7. Statement-1: p-Hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid. [IIT - 2007]
O
HBr
8. In the reaction OCH3 the products are [JEE -2010]
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ALCOHOL PHENOL AND ETHER
9. In the following reaction, the products (s) formed is (are) [JEE Advanced 2013]
OH
CHCl3
?
OH
CH3
OH O OH OH
OHC CHO CHO
IA
10. The correct combination of names for isomeric alcohols with molecular formula C4H10O is/are
(A) tert- butanol and 2-methylpropan -2-ol [JEE Advanced 2014]
(B) tert-butanol and 1, 1-dimethylethan-1-ol
(C) n-butanol and butan-1-ol
D
(D) isobutyl alcohol and 2-methylpropan -1-ol
11. Sodium phenoxide when heated with CO2 under pressure at 125ºC yields a product which on acetylation produces
C.
ONa
N [IIT-JEE 2014]
SI
125º B
+ CO2
5Atm Ac2O
OH
OH OCOCH3 OCOCH3 COCH3
COOCH3 COOH
O
12. The acidic hydrolysis of ether (X) shown below is fastest when, [JEE Advanced 2014]
acid
OR OH + ROH
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ALCOHOL PHENOL AND ETHER
H2O
HgSO 4, H 2SO 4
i. EtMgBr, H2 O
C8H8O Y
O OH
OH
CHO
(A) CH3 (B) CH3 (C) (D)
14. The desired product X can be prepared by reacting the major product of the reaction in LIST-I with one or more
IA
appropriate reagents in LIST - II.
(given, order of migratory aptitude : aryl > alkyl > hydrogen) [JEE Advanced 2018]
O
Ph
D
OH
Ph
Me
X
LIST – I
HO
Ph
Ph N LIST – II
SI
Me
(P) + H2SO4 (1) I2 , NaOH
OH
Me
Ph
O
H2N
Ph H
(Q) + HNO2 (2) [Ag(NH3)2]OH
O
OH
Me
Ph
HO
ET
(5) NaOBr
The correct option is
(A) P 1 ; Q 2, 3 ; R 1, 4 ; S 2, 4
(B) P 1, 5 ; Q 3, 4 ; R 4, 5 ; S 3
(C) P 1, 5 ; Q 3, 4 ; R 5 ; S 2, 4
(D) P 1, 5 ; Q 2, 3 ; R 1, 5 ; S 2, 3
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ALCOHOL PHENOL AND ETHER
ANSWER KEY
EXERCISE - 1
1. C 2. A 3. C 4. C 5. C 6. C 7. D 8. B 9. A 10. C 11. B 12. C 13.
A 14. A 15. A 16. B 17. D 18. A 19. C 20. B 21. A 22. C 23. D 24. C 25. A
26. A 27. B 28. A 29. A 30. B 31. A 32. A 33. A 34. B 35. C 36. A 37. B 38.
D 39. C 40. C 41. C 42. B 43. A 44. A 45. B 46. B 47. C
IA
EXERCISE - 2 : PART # I
1. 3 2. 2 3. 3 4. 3 5. 1, 2, 3 6. 1 7. 2 8. 1 9. 2 10. 2 11. 1 12. 4 13. 2
14. 3 15. 4 16. 2 17. 4 18. 1 19. 2 20. 2 21. 3
D
1. D 2. A
N
PART # II
SI
3.
O
O
ET
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ALCOHOL PHENOL AND ETHER
CH 2 O
4. (P) CH3 – CH2 – O – C – CH3 ; (Q) CH3CH2OH ; (R) CH3 – C – CH 3
When ethylene reacts with dil. H2SO4 CH3CH2 is produced during rate determining step, whereas P gives resonance
stabilized intermediate.
IA
C
5. C CH2 CH2 H 6. B 7. D 8. D 9. B, D
D
(X) (Y)
10. A,C,D 11. C 12. C 13. C 14. D
N
SI
O
O
ET
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