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Alcohol, Phenol and Ether
Alcohol, Phenol and Ether
REVISION
OF
ORGANIC CHEMISTRY
FOR JEE ADVANCED
BY
NAVNEET JETHWANI
ALCOHOL, PHENOL
&
ETHER
ETOOSINDIA
INDIA’S NO. 1 ONLINE COACHING
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H 2SO4
Pr oduct
Ans. (A)
2. Predict the product when given compound reacts with LiAlH4 :
O O
C C
H OCH3
(A)
O
O
C O CH3
C O CH3
(A) (B)
O
C
H
(C) (D)
Ans. (C)
18
CO2H CH2
H
3. + 18
(A) ; Product (A) is :
CO2H CH2
O O
18
C O CH2 C O CH2
(A) (B) 18
C O CH2 C O CH2
O O
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18
O
O O
C O CH2
(C) (D) H O C C O CH2 CH2
C O CH2
18
O
Ans. (B)
O O NaBH4
4. (P)
O
O
LiAlH
(Q)
4
O LiAlH
4
(A)
5. xAc2O
O
(B)
6. For the following reaction, select the statement that best describes the change.
RCH2OH + PCC [C5H5NH+ClCrO3–]
(A) The alcohol is oxidized to an acid, and the Cr(VI) is reduced
(B) The alcohol is oxidized to an aldehyde, and the Cr(VI) is reduced
(C) The alcohol is reduced to an aldehyde, and the Cr(III) is oxidized
(D) The alcohol is oxidized to a ketone, and the Cr(VI) is reduced
Ans. (B)
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7. Two unknown compounds X and Y, both having molecular formula C4H8O, give following results with four
chemical tests.
O
(1)sodium acetylide
(2)H O,H to neutralize
Product
2
O OH HO
Ans. (C)
OH OH
(A) OH +OH
PCC (1)MeMgBr NaBH 4 ,EtOH
9. (B)
(2)H O
(C) (D)
H 3
OH OH OH OH OH OH
OH
(A) (B) (C) (D)
OH
Ans. (B)
When Grignard reagent reacts with (B) product (D) will obtained. Reactant (A) of the above reaction is :
OH
(A) (B) OH (C) (D)
OH OH
Ans. (A)
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11. Ph CH2 CH K
CH3 C2 H5 Br
(A)
OH
Product (A) in above reaction is :
(A) Ph CH2 CH CH3 , (inversion) (B) Ph CH2 CH CH3 , (retention)
OEt OEt
(C) Ph CH2 CH CH3 , (racemic) (D) Ph – CH = CH – CH3
OEt
Ans. (B)
O O
CH3 CO C OCH3 (i)LiAlH4
12.
(ii)H2 O
(A) ; Product (A) of the reaction is
(96%)
OH OH OH CH2 OH OH CH2OH O
Ans. (C)
13. What is the major organic product of the following sequence of reactions ?
O
O CH2 OH
CH CO2Et +
(A) (B)
H
CH3
O O
(A) (B)
CH2 CH OH CH CH2 OH
CH3 CH3
O O
(C) OH (D)
C CH3 CH2 CH2 OH
CH3
Ans. (B)
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O
O
O O
O O O O
15.
(A)
(B)
(C)
(D)
CO2CH3
CO2CH3 CHO
CH2 OH CHO
Identify correct combination :
CH2 OH
(A) (A)= (B) B = NaBH4 (C) (C) = KMnO4 (D) (D) = H3O
CH2 SH
Ans. (D)
O O
CH3 C OH + CH3
OH
cat.
CH3 C O CH3 + H2O
(A) The use of equimolar quantities of CH3OH and CH3COOH will give the greatest yield of the ester at
equilibrium.
(B) Removal of water will increase the amount of ester at equilibrium.
(C) Addition of CH3COOCH3 will cause the formation of an equal number of moles of water.
(D) Application of pressure increases the amount of ester at equilibrium
Ans. (B)
O
OH
Pbr3 Mg (1) V CH3 C Cl
W X (2) H O+ Y Z
17. ether 3
Na2Cr 2O7
V
Product Z of above reaction is :
O
O
O C CH3
O C CH3
(A) (B)
O O
O C CH3 O C CH3
(C) (D)
Ans. (B)
18. Find out the reaction in which obtained product give positive isocyanide test :
O O
(A) LiAlH4 (B) NaBH 4
NH2 NH2
NH LiAlH4
NH NaBH 4
(C) (D)
O O
Ans. (A)
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O OH
O O
19. H
O O
In the above given compound how many functional group reduced by LAH (Lithium aluminium hydride) and
SBH (sodium borohydride) respectively ?
(1) 4, 4 (2) 4, 2 (3) 3, 4 (4) 4, 2
Ans. (B)
20. Correct order of dehydration of following alcohols will be :
OH OH OH OH
1 2 3 4
(A) 1 < 2 < 3 < 4 (B) 4 > 3 > 1 > 2 (C) 4 > 2 > 1 > 3 (D)1 > 3 > 4 > 2
Ans. (C)
OH OH
Et Me
+
21. H ? product is :
Et Me
(A) (B)
Me O O Et
Et Me
(C) (D)
Ans. (D)
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Mg Hg Conc. H2SO4
Q.22 2Ph C CH3 Product
H 2O
O
(A) Ph C C Ph (B) CH 3 C C CH 3
O O O O
Ph Ph
(C) Ph C C CH3 (D) Ph C C CH3
O O
CH3 CH3
Ans. (C)
CH3 CH3
CH3 CH3 OH
O O
(C) (D)
Ans. (B)
25. Consider the reaction of HI with the following :
(I) (II)
O
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Br
Mg (i) 14CO2 NaHCO3
26 (A) (B) (C) gas, product C is :
(ii) H+/H2O
(A) CO (B) 14CO2 (C) CO2 (D) A mixture 14CO2 and CO2
Ans. (C)
Product of reaction is :
O
OH CH3
(A) (B) CH C
O CH3
O
CH3 OH
(C) (D)
O CH2 C CH2 OH CH2 CH2 C CH3
O
CH3 CH3
Ans. (D)
O
O
Br2/h Mg. 1. Conc.H2SO4 O3
28. A B C D E
Et2O 2. H3O
+ Zn/H2O
CH3
Ans. (C)
COOH MgBr
29. + X+Y
(1 eq.)
SO3H
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COOH MgBr
SO3H
COOH
SO3MgBr
Ans. (C)
O
PhMgBr (excess)
30. Cl C Cl (X) ; Product (X) is :
H 3O +
O O O
OH
O
(A) Ph C Cl (B) Ph C Ph (C) Ph C Ph (D) Ph C Ph
Ph
Ans. (C)
SH
SH
OC2H5 (1) 'X' CH3MgBr
31. HO
HO
O HO
32.
O
Identify (X) :
(A) (B)
OH
OH O
HO
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OH
(C) (D)
HO O OH
Ans. (A)
33. Predict the reducing agents in following reaction.
H
O ?
OH
(A) LiAlH4 (B) NaBH4 (C) H2 / Pt, (D) Both (A) and (B)
Ans. (C)
34. Predict major organic product from the following reaction:
H3C O NaBH4
A
LiAlH4
B
O
OH OH O OH
OH OH O OH
(A) A B (B) A B
O OH OH OH
OH OH O
OH
OH O
O OH
(C) A B (D) B
A
OH OH OH
O
Ans. (B)
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OMe OMe
H3C C CH2 CH3 CH3
(A) (B) H3C CH CH
CH3
CH3
Ans. (A)
36. Find out correct product of reaction :
HBr
(Excess)
Br
(A) (B)
O OH Br
(C) (D)
Br Br Br OH
Ans. (B)
37. , S is :
OH
OH
OH
(A) (B) (C) (D) OH
Ans. (B)
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38.
HO OH HO CH2 OH
(A) (B)
HO CH2 OH
(C) (D)
Ans. (C)
(A) Racemic mixture (B) Diastereomers (C) Meso (D) Optically pure
Ans. (B)
O OH
H3C C CH2 CH2CO2CH3 H3C CH CH2 CH2 CH2OH
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Product E is
(A) (B)
I
CH3 CH2I CH2CH3
(C) (D)
I
I
CH3 CH3
Ans. (D)
H2O dil. H2SO4 H2
42. In the reaction sequence , CaC2 A B Ni C , true about the product C is
Hg+2
CH3CH2OH
43. CH CH 2 H2SO4
CH2CH3
(A) (B) CH2 CH3
OCH2 CH3
OCH2 CH3
CH2CH3
Ans. (A)
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H2O/H
44. 'X' ; Product ‘X’ will be
O O
CH3
(A) (B)
Ans. (A)
SOCl 2 Mg. O
45. Product
Pyridine, Et 2O H
O CH2OH
(A) (B)
(C) (D)
Ans. (B)
46. Select the major product of following reaction :
CH 3CH 2O
Cl
O O
(A) (B)
OCH2CH3
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OCH2CH3
(C) O (D)
Cl
Ans. (D)
47. Identify the final product of following sequence of reactions :
(A) (B) H
O
(C) (D) OH
OH
Ans. (B)
48. The product of the reaction is :
O
1. KH
HS 2. H 2O
OH S O
S
(A) (B)
OH
Ans. (A)
49. Identify the major product of reaction :
OH
TSCl KSH
Pyridine
D
H
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SH SH
(A) (B)
D D H
H
D
(C) (D) No reaction
H
Ans. (B)
CH3 CH3
(A) (B) C C
H H
(C) (D)
Ans. (C)
18
O +
H3O
51. ; Major organic product
18 18 18
OH OH OH OH
18 18
O O O
(A) (B) (C) (D)
Ans. (D)
52. Phenol and ethanol are distinguished by the reaction with
(A) Red litmus (B) NaHCO3 (C) FeCl3 (D) Na
Ans. (C)
53. Which of the following reactions would give the best yield of t-butyl methyl ether ?
H 2SO4
(A) (CH3)3C –OH
140 C
(B) (CH3)3C–Br + CH3OH
(C) (CH3)3C–Br + CH3O Na (D) (CH3)3C – OK + CH3Br
Ans. (D)
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CH CH2
CH2CH3 C
OH
54. B A
CH2CH2 OH
CHCH3
OH
CH3
TsCl KSH
H OH (A) Products
55.
Et
(1 mole)
(Assuming all the substrate convert into substitution products containing 0.05 mole of S-configuration) Calculate
the percentage of SN2 mechanism.
(A) 90% (B) 80% (C) 70% (D) 95%
Ans. (A)
(i )CH 3CN (i )RMgX
56. RMgX
(ii )H 2 O
(A)
(ii)H 2O
(B) , (B) will be
OH OH
Ph H 2SO 4 I
LiAlH 4 H
Ph (1) (2)
II
(3)
III
O O
Ph
Ph
(A) I = Ph (B) I = Ph
Ph Ph
Ph Ph
(C) III = (D) III =
Ans. (B)
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H /
58.
Catalyst Product
OH
Ans. (C)
CH3
HI(cold)
O A B
59. conc.
A, B are
CH3
OH
OH
CH3
(A) H (B) C2H5I (C) CH3I (D)
H
(R)
(S)
Ans. (B)
60. The end product of following reaction is :
Me
Na Me-I
Dry Ether
(A)
H OH Ether
SOCl2 NaOMe (B)
Low Temp.
Et
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ETOOSINDIA F.T.R. BY N.J. SIR
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61. Which of the following is/are the proper sequence of reagents for the conversion
OH Ph
OH
OH
O
||
(A)
PBr3 Mg/Et 2O
Ph C H
H2SO4
OsO4
H 2O
O
||
(C) CH3MgBr
H 2SO 4
Ph C H
OsO4 alkaline
H O 3
Ans. (D)
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Br
Ans. (B,C,D)
2. Which of the following reactions proceeds with inversion of configuration ?
Me Me
Na CH3Br TsCl CH3ONa
(A) H OH (B) H OH
Et Et
Me Ph
PCl5 CH3ONa SOCl2 KCN
(C) H OH (D) H OH
Et CH3
Ans. (B, D)
3. Products obtained in the following reaction.
(i) CH3MgCl
O
(ii) NH4Cl
OH
(A) (B)
OH
(C) OH (D)
OH
Ans. (A, B, D)
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4. Which of the following are correct regarding the products of the given reaction
Me
Me
H CN aqueous acetone
H H
H
Cl
OCH3
Me Me Me
Me Me H Me
H H
CN OH CN HO CN
H H H H H H
H H
OH H H
(A) only X and Z are formed (B) Y > Z (amount) (C) X > Y (amount) (D) Y > X (amount)
Ans. (B, D)
H H
TsCl NaBr
5. X Y. X and Y are :
Pyridine
CH3 OH
H H H Br H
H H
(A) X = (B) Y = (C) X = (D) Y =
||
6. What are the possible intermediates of the following reaction which form during this reaction path way ?
H3PO4
Δ
Ans. (A, B, D)
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CH3 CH3
CH3 CH3
(D) Br + RO N a OR
Ans. (B, D)
8. What are the products expected in the following reactions ?
O O
CH2N 2
C6H5 – C – CH2– C – CH3
Ether
OCH 3 O O OCH3
OCH3 O O OCH3
CH2 CH2
Ans. (A, B)
9. The intermediate stages in the conversion
OH OH
(A) (B)
(C) (D)
Ans. (A, B, C, D)
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OH
25°C (A)
Conc. Conc. H2SO4
10. H2SO4
at 100°C
100°C (B)
OH
SO3H
SO3H
(II)
(I)
12. Which of the following paths is/are feasible for the preparation of ether (A) ?
Me
(A) Path I: Ph + EtONa
Br
Me
(B) Path II: Ph + EtBr
Me
ONa
Ph
1. Hg(OCOCF3)2
OEt
(C) Path III: Ph + EtOH
2. NaBH4 (A)
1. Hg(OCOCF3)2
Me
(D) Path IV : Ph + EtOH
2. NaBH4
Ans. (B, C)
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13. Which of the following statements is/are correct about the following reactions ?
Cl OH
NO2 NO2
1. NaOH HNO3
Path (I)
2. H3O
H2SO4
OH
NO2 NO2 O2N NO2
(A) (B)
NO2
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O O
Me O
(A) (B) (C) (D)
O Me
Me Me
Et
Ans. (A)
17. What is the major product of the following reaction ?
NaBH 4
product
CO2H
OH OH
O OH
Ans. (A, B)
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Misc. Exercise
Subjective Questions
PCl5 +
KCN H 3O NH3 heat
1. C2H5OH (A) (B) (C) (D) (E)
PBr5 KOH(Alc.) HBr NH3
2. CH3CH2CH2OH (A) (B) (C) (D)
3. Provide products in the following reactions :
(c) mCPBA
CH3MgBr
(a) +
A
H3O
O
H3C
CH3MgBr
(b) CH2CH2CH3 +
A
H3O
H3C O
mCPBA C2 H 5MgBr
(c) CH3CH=CH2 A +
B
H 3O
5. Compound (A) C4H10O reacts rapidly with metallic sodium, but undergoes almost no reaction with Lucas reagent.
When (A) is treated with hot concentrated sulphuric acid, a new compound (B) C4H8 is formed. If C4H8 is hydrated
with sulphuric acid a new compound (C) C4H9OH is formed, which is almost inert to metallic sodium but reacts
rapidly with Lucas reagent. What are (A), (B) and (C) ?
6. A compound (X) containing C, H and O is unreactive towards sodium. It does not add bromine. It does also not
react with Schiffs reagent. On refluxing with an excess of HI, (X) give only (Y). (Y) on hydrolysis gives (Z) which
can be converted to (Y) by the action of P + I2. Compound (Z) on oxidation gives an acid of equivalent weight 60.
What are (X), (Y) and (Z) ?
7. An alkyl iodide (A) C3H7I when treated with an aqueous solution of an alkali, (B) is formed. (B) on oxidation
produced only one compound (C). C3H7MgBr when treated with (C) gives (D) C6H14O which reacts rapidly with
Lucas reagent. Identify (A) to (D).
8. Compound (A) reacts with sodium to liberate H2, forming a compound (B). When (A) it treated with HCl + ZnCl2,
an immediate reaction takes place liberating (C). When (A) is heated with H2SO4, (D) is formed. Ozonolysis of (D)
gives a 3 carbon aldehyde and 3 carbon ketone. What are (A), (B), (C) and (D) ?
9. An organic compound (A) C4H10O reacts with HI giving a compound (B) C4H9I, which on reduction gives a
normal hydrocarbon having four carbon atoms. On oxidation (A) gives (C) C4H8O and then acid (D) C4H8O2.
What are (A) to (D) ?
10. An organic compound (A) C3H8O on treatment with excess of hot conc. H2SO4 gives a compound (B). (B) on
treatment with HBr gives (C) which on hydrolysis yields (A). (C) when dissolved in ether and treated with
sodium gives (D). What are (A) to (D) ?
11. An alcohol (A) on treatment with conc. H2SO4 gave an alkene (B). The compound (B) on reacting with Br2 water
and subsequent dehydrobromination with NaNH2 produced a compound (C). The compound (C) with dil. H2SO4
in presence of HgSO4 gave a compound (D). The compound (D) can also be obtained by oxidation of (A) by
KMnO4 or from dry distillation of Calcium acetate. Name (A), (B), (C) and (D) explain reactions.
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Comprehension
Paragraph - 1 (12 to 14)
Alcohols are converted to tosylates by treatment with p-toluene sulfonyl chloride (TsCl) in presence of pyridine.
This overall process converts a poor leaving group (OH) into better one (OTs) . A tosylate is a better leaving
group because its conjugated acid p-toluene sulfonic acid is strong acid.
Because alkyl tosylates have better leaving tendency they undergo both nucleophilic substitution and -
elimination.
O
Pyridine
CH3CH2 OH + Cl S CH3
O
poor leaving Tosyl chloride
group (TsCl)
O
CH3CH2 O S CH3 + + Cl
+
O N
H
or
E2
KOH + H CH2 CH2 OTs H 2C CH2 + KOTs
(Alcoholic)
H3C H
H C
(A) C CN (B) CH3 CH
CH3 CH2 CH3
CH3 H
H H3C C CH2CH3
(C) NC C (D)
CH2CH3 NC
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 29
Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING
Pyridine CH3CH 2ONa
OH + Ts Cl
OTs
(A) (B) H
O
(C) (D) OH
OH
H H H
O O O
+ +
CH2 – C – CH3 CH2– C – CH3 CH2– C – CH3
CH3 CH3 CH3
(I) (II) (III)
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Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING
Structure II and III show that the oxirane carbon share part of positive charge. The tertiary carbon bear a larger part
of positive charge and it is more strongly electrophilic. The bond between tertiary carbon and oxygen is weaker
implying a lower transition state energy for attack at the tertiary carbon. Attack by the weak nucleophilic is sensitive
to the strength of electrophilic is sensitive to the strength of electrophile. Centre attack takes place at more electrophilic
carbon which is usually the more substituted carbon because it can better support the positive charge.
15. What will be the products in following reactions
CH 3– CH 2ONa
O X
CH 3– CH 2OH
CH3
OH H OCH2CH3
(A) (B)
CH3 OCH2–CH3 CH3 H
H
(C) (D)
CH3 CH3
H2SO4
O Y
16. CH3– CH2–OH
CH2–CH3
C2 H5
(A) (B)
C2H5
O18
+
H2O/H
17. CH2 CH Z
CH3
CH3 CH3
CH3
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Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING
O
CH3–ONa
18. P:
CH3–OH
OH OCH3
OH OH
(A) OCH3 (B) (C) (D)
H2SO4
19. Q:
CH3–OH
(A) (B)
Phenols are converted into their salts by aqueous NaOH but not by aqueous bicarbonates. The salts are converted
into the free phenols by aqueous mineral acids, carboxylic acid or carbonic acids. Most phenols have Ka value of
about 10–10, and are tremendously more acidic than alcohols. The difference in acidity are due to difference in
stabilities of reactants and products. Phenol and phenoxide ions contain benzene ring and therefore must be hybrid
of Kekuley structures
OH OH O O
and
Being basic, oxygen can share more than a pair of electron with the ring.
and
Since energy must be supplied to separate opposite charge, the structure of phenols should contain more energy.
The net effect of resonance is therefore to stabilise the phenoxide ion to a greater extent than the phenol and thus
to shift the equilibrium towards ionization and make Ka larger than for an alcohol.
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ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING
OH
Potential Energy
A
(B) Curve B represent the ionisation of Phenols
B
(C) Curve A represents the ionisation of phenol
(D) None
Progress of reaction
+OH O
OH
OH OH OH OH
NO2 CH3
(B) > > (C) H2CO3 > > CH3 – OH
NO2
O
(D) R– O is more stable than
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 33
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ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING
(A) KMnO 4
(B) (C9H10O3)
One mole MeI
OH
OH
COOH Br COOH Br
Br Br
(A) , (B) ,
OMe Br OMe OH
OH OH OMe OH
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ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING
Br Br Br
(C) , (D) ,
OMe Br OMe OH OMe
OH OH OMe OH
H H
(I)
regiospecifivity
1. Hg(OCOCF3 ) 2 PhOH
(B) (I) 2. NaBH 4 q. Anti-hydration with Markovnikov’s regiospecifivity
1. B2 H6 /THF
(C) (I)
r. Cyclic intermediate transition state
2.H2 O2 / OH
1. B2 H 6 / THF
(D) Ph Me
2. CH 3COOH
s. Overall non-stereospecific
t. Overall stereospecific
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Kota, Rajasthan – 324005 Mob. : 9214233303