FEAT 1 Alcohol, Ether and Epoxide
QUESTION BANK FOR JEE
Objective Questions:
Q1. The following transformation involves a carbocation rearrangement. The carbocation is generated by
protonation of the hydroxyl group, followed by the loss of water. Which bond has to migrate in the carbocation
to yield the product indicated (after the deprotonation)?
(a) a
(b) b
(c) c
(d) d
Q2. Identify the major product.
Q3.
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FEAT 2 Alcohol, Ether and Epoxide
Q4. Predict the product when given compound reacts with LiAlH4 :
Q5. Predict the product when given compound ( 𝐴, in the above question 4) reacts with NaBH4 .
Q6.
The labelled −O18 will be in:
(a) H2 O
(b) Methyl benzoate
(c) Both (a) and (b)
(d) Benzoic acid
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FEAT 3 Alcohol, Ether and Epoxide
Q7.
Q8. Which is oxidized most easily?
Q9.
Q10. Which of the following react with HBr at faster rate?
Q11.
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FEAT 4 Alcohol, Ether and Epoxide
Above conversion can be done by :
(a) NaBH4
(b) LiAlH4
(c) PCC
(d) KMnO4
Q12.
Q13.
Q14. Predict the major product of the given reaction.
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FEAT 5 Alcohol, Ether and Epoxide
Q15. Identify the major product,
Q16.
Q17.
Q18.
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FEAT 6 Alcohol, Ether and Epoxide
Q19.
Q20.
Q21.
Q22. Consider the following alcohols,
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FEAT 7 Alcohol, Ether and Epoxide
The order of decreasing reactivities of these alcohols towards nucleophilic substitution with HBr is:
(a) III > I > IV > II
(b) III > I > II > IV
(c) I > III > IV > II
(d) I > III > II > IV
Q23.
Sum of number of alcoholic groups in product (𝑃) and (𝑄) is:
(a) 1
(b) 2
(c) 3
(d) 5
Q24. In presence of dil. HCl, compound A is converted to a constitutional isomer (B), compound B is:
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FEAT 8 Alcohol, Ether and Epoxide
Q25.
Q26.
Product of the reaction is:
(a) Racemic
(b) Diastereomer
(c) Meso
(d) Optically pure
Q27.
Chemist added extra 0.5 mole of Et-Li in above reaction to obtain product (A), which is?
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FEAT 9 Alcohol, Ether and Epoxide
Q28.
Q29.
(a) SN1
(b) SN2
(c) SN − NGP
(d) SN − Ar
Q30.
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FEAT 10 Alcohol, Ether and Epoxide
Q31.
Q32. Which is the best reagent to convert isopropyl alcohol to isopropyl bromide ?
(a) HBr
(b) SOBr2
(c) Br2
(d) CH3 MgBr
Q33.
Q34.
Total number of stereoisomers of product (𝐵) will be:
(a) 2
(b) 3
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FEAT 11 Alcohol, Ether and Epoxide
(c) 4
(d) 5
Q35.
Q36.
Q37.
For the above conversion the correct order of reagents used is:
(a) 1 → 2 → 3 → 4
(b) 1 → 4 → 3 → 2
(c) 1 → 4 → 2 → 3
(d) 2 → 3 → 4 → 1
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FEAT 12 Alcohol, Ether and Epoxide
Q38.
Find missing reagents.
(a) 𝑥 = LiAlH4 , 𝑦 = NaBH4
(b) 𝑥 = LiAlH4 /AlCl3 , 𝑦 = LiAlH4
(c) 𝑥 = LiAlH4 , 𝑦 = LiAlH4 /AlCl3
(d) 𝑥 = H2 /Ni, 𝑦 = H2 /Pt
Q39. In solvolysis of 1, 2-dimethyl propyl p-toluene sulfonate in acetic acid at 75∘ C, (alkene + substitution
products) will be formed by mechanism?
(a) SN2 , E2
(b) SN2 , E1
(c) SN1 , E2
(d) SN1 , E1
Q40.
𝑥 = moles of anhydride consumed
(a) 1
(b) 2
(c) 3
(d) 4
Q41. Identify product when (𝑅) - and (𝑆) − 2 - butanol reacts with (𝑅, 𝑅) tartaric acid in acidic medium.
(a) Racemic
(b) Diastereomer
(c) Meso
(d) Pure enantiomer
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FEAT 13 Alcohol, Ether and Epoxide
Q42. An alcohol of formula C9 H12 O reacts with Na2 Cr2 O7 to form a compound having formula C9 H10 O.
The original alcohol might be:
Q43. An optically active alcohol of formula C9 H12 O2 produced the following compound when refluxed
with KMnO4 .
What is structure of (A)?
Q44. Which are not cleaved by HIO4 ?
Q45. Which of the following reactions require an oxidising agent?
(a) CH3 − CH = CH2 ⟶ CH3 − CH2 − CH3
(b) CH3 − CH2 OH ⟶ CH3 CHO
(c) CH3 − CH2 Cl ⟶ CH3 − CH3
(d) CH3 − CH2 OH ⟶ CH3 − CH2 Cl
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FEAT 14 Alcohol, Ether and Epoxide
Q46 What is the major product of the following reaction?
Q47. Which of the esters shown, after reduction with LiAlH4 and aqueous workup, will yield two
molecules of only a single alcohol?
(a) CH3 CH2 CO2 CH2 CH3
(b) C6 H5 CO2 CH2 C6 H5
(c) C6 H5 CO2 C6 H5
(d) None of these
Q48. For the following reaction, select the statement that best describes the change.
𝑅CH2 OH + PCC[C5 H5 NH + 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
Q49. What is the product of the following reaction?
(a) Only 1
(b) 1: 1 mixture of 2 and 3
(c) Only 2
(d) 1: 1: 1 mixture of 1,2, and 3
Q50. An organic compound 𝐵 is formed by the reaction of ethylmagnesium iodide (CH3 CH2 MgI) with a
substance 𝐴, followed by treatment with dilute aqueous acid. Compound 𝐵 does not react with PCC
in dichloromethane. Identify 𝐴 ?
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FEAT 15 Alcohol, Ether and Epoxide
Q51. Which of the following reagents would carry out the following transformation? (𝐷 = 2 𝐻)
(a) NaBD4 in CH3 OH
(b) LiAlH4 , then D2 O
(c) NaBD4 in CH3 OD
(d) LiAlD4 , then D2 O
Q52. Which sequence of steps describes the best synthesis of 2-methyl-3-pentanone?
Q53. Diols (I-IV) which react with CrO3 in aqueous H2 SO4 and yield products that readily under go
dercarboxylation on heating, are:
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FEAT 16 Alcohol, Ether and Epoxide
Q54. Which of following compounds are not oxidized by HIO4 ?
(a) 5, 6, 7
(b) 4, 5, 6, 7
(c) 6, 7
(d) 3, 4, 5, 6, 7
Q55.
Q56. Unknown (A) in the reaction (given in Q. 55) is:
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FEAT 17 Alcohol, Ether and Epoxide
Q57. In the given table, identify the incorrect option. The digit in box indicate the moles of that substance.
Q58.
Q59. A. Given are the structures of cyclic D-glucoside. Moles of HIO4 consumed with 𝑋 and 𝑌 are
respectively:
(a) 2,2
(b) 3,3
(c) 2,3
(d) 3,2
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FEAT 18 Alcohol, Ether and Epoxide
B. Moles of formic acid formed in 𝑋 and 𝑌 respectively are:
(a) 1,2
(b) 2, 1
(c) 2,3
(d) 3,2
C. Moles of HCHO formed are:
(a) 1,1
(b) 2,2
(c) 1,2
(d) 2,1
Q60. In which of the following group, each member gives positive iodoform test?
(a) methanol, ethanol, propanone
(b) ethanol, isopropanal, methanal
(c) ethanol, ethanal, isopropyl alcohol
(d) propanal, propanol-2, propanone
Q61.
Q62. A
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FEAT 19 Alcohol, Ether and Epoxide
Q63. Two unknown compounds 𝑋 and 𝑌, both having molecular formula C4 H8 O, give following results
with four chemical tests.
Q64.
Q65. Assign the structure of major product (X) of the reaction given below.
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FEAT 20 Alcohol, Ether and Epoxide
Q66.
Q67.
Q68.
In above reaction molecular formula of glycerol increases by :
(a) C4 H4 O2
(b) C6 H6 O6
(c) C6 H6 O2
(d) C6 H6 O3
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FEAT 21 Alcohol, Ether and Epoxide
Q69. Give the best conditions for this transformation:
(a) CH3 OH, H + (cat.), heat
(b) H2 O, H + (cat.), heat
(c) Mg, ether, CH3 OH
(d) SOCl2 , CH3 OH
Q70. Give the major organic product of the following reaction.
Q71.
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FEAT 22 Alcohol, Ether and Epoxide
Q72. Select the best method for the preparation of the following compounds:
(a) reaction of cyclohexanone with CH3 Li
(b) reaction of 1-methylcyclohexene with Hg(OAc)2 followed by NaBH4
(c) reaction of cyclohexene with BH3 ; NaOH/H2 O2 , following by CH3 Br
(d) reaction of cyclohexene with MCPBA, followed by CH3 MgBr
Q73. Identify the reagents (1-4), required for the transformations shown and arrange them in correct order.
(1) LAH (LiAlH4)
(2) OsO4
(3) NaIO4
(4) NaBH4
(a) 1 → 3 → 4 → 2
(b) 2 → 3 → 1 → 4
(c) 2 → 1 → 3 → 4
(d) 1 → 2 → 3 → 4
Q74. Which describes the best stereochemical aspects of the following reaction?
(a) Inversion of configuration occurs at the carbon undergoing substitution.
(b) Retention of configuration occurs at the carbon undergoing substitution.
(c) Racemization (loss of configuration) occurs at the carbon undergoing substitution.
(d) The carbon undergoing substitution is not stereogenic
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FEAT 23 Alcohol, Ether and Epoxide
Q75. Which of following is an example of Pinacol-Diazotization?
Q76.
Q77. A solution of Ph3 CCO2 H in conc. H2 SO4 gives (𝑋) when poured into methanol 𝑋 is:
Q78.
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FEAT 24 Alcohol, Ether and Epoxide
Q79. In the given pair of alcohol, in which pair second alcohol is more reactive than first towards hydrogen
bromide?
Q80. Rank the transition states that occur during the following reaction steps in order of increasing stability
(least → most stable)
+
1 H3 C − O2 H2 ⟶ CH3+ + H2 O
+
2 (CH3 )3 C − OH2 ⟶ (CH3 )3 C+ + H2 O
+
3 (CH3 )2 CH − OH2 ⟶ (CH3 )2 CH + + H2 O
(a) 1 < 2 < 3
(b) 2 < 3 < 1
(c) 1 < 3 < 2
(d) 2 < 1 < 3
Q81.
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FEAT 25 Alcohol, Ether and Epoxide
Q82. In which of the following reactions hydrogen gas will not be evolved?
Q83.
Q84.
Q85.
Above conversion can be acheived by:
(a) LiAlH4
(b) NaBH4
(c) H2 /Ni
(d) CrO3
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FEAT 26 Alcohol, Ether and Epoxide
Q86.
Q87.
Q88. What is the major product of the following reaction?
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FEAT 27 Alcohol, Ether and Epoxide
Q89. The major reason that phenol is a better Bronsted acid than cyclohexanol is that :
(a) it is a better proton donor.
(b) the cyclohexyl group is an electron donating group by induction, which destabilizes the anion
formed in the reaction by resonance.
(c) phenol is able to stabilize the anion formed in the reaction.
(d) the phenyl group is an electron withdrawing group by induction, which stabilizes the anion
formed in the reaction.
Q90. Which of these reagents would accomplish the following reduction?
(a) NaBH4
(b) LiAlH4
(c) 1 mole2 , poisoned catalyst, low pressure
(d) H3 O+
Q91.
Q92.
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FEAT 28 Alcohol, Ether and Epoxide
Q93.
Q94.
Q95. Select the correct statement.
(a) Solvolysis of (CH3 )2 C = CH − CH2 − Cl in ethanol is over 6000 times greater than alkyl chloride
(25∘ C)
(b) CH3 − CH = CH − CH2 − OH when reacts with HBr give a mixture of 1-bromo-2-butene and 3-
bromo 1-butene
(c) When solution of 3-buten-2-ol in aqueous sulphuric acid is allowed to stand for one week, it was
found to contain both 3-buten-2-ol and 2-buten-1-ol
(d) All of these
Q96.
Q97.
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FEAT 29 Alcohol, Ether and Epoxide
Q98. Iodoform can be obtained on warming NaOH and iodine with:
Q99. Which of these is a reducing agent?
(a) CrO3 /H +
(b) KMnO4
(c) LiAlH4
(d) O3
Q100.
Q101.
Q102.
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FEAT 30 Alcohol, Ether and Epoxide
Q103.
Q104.
Above reaction is/an example of :
(a) esterification
(b) saponification
(c) trans-esterification
(d) hydrolysis
Q105. What is the major organic product of the following sequence of reactions?
Q106. The structure of the product formed in the reaction given below is:
Q107.
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FEAT 31 Alcohol, Ether and Epoxide
Q108.
Q109.
Ratio of moles of formic acid obtained in reaction (i) and reaction (ii) is :
(a) 3/4
(b) 4/5
(c) 1
(d) 5/4
Q110. Which of the following compound gives 2HCHO, CO2 , HCO2 H when oxidised by periodic acid?
Q111. Hydration of 3-phenylbut-1-ene in dil. H2 SO4 will give mainly:
(a) 3-Phenylbutan-1-ol
(b) 3-Phenylbutan-2-ol
(c) 2-Phenylbutan-2-ol
(d) 2-Phenylbutan-1-ol
Q112. Decarboxylation of sodium salicylate with soda lime forms :
(a) Salicylic acid
(b) Phenol
(c) Benzene
(d) None of these
Q113.
(a) 1
(b) 2
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FEAT 32 Alcohol, Ether and Epoxide
(c) 3
(d) 4
Q114.
Q115.
Q116.
Q117. In the Libermann's nitroso reaction, sequential changes in the colour of phenol occurs as :
(a) Brown or red ⟶ green ⟶ deep blue
(b) Red ⟶ deep blue ⟶ green
(c) Red ⟶ green ⟶ white
(d) White ⟶ red ⟶ green
Q118. Ethanol when reacts with PCl5 gives 𝐴, POCl3 and HCl. 𝐴 reacts with dry Ag 2 O to form 𝐵 (major
product) and AgCl. 𝐴 and 𝐵 respectively are :
(a) C2 H5 Cl and C2 H5 OC2 H5
(b) C2 H4 and C2 H5 OC2 H5
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FEAT 33 Alcohol, Ether and Epoxide
(c) C2 H6 and C2 H5 OC2 H5
(d) C2 H6 and C2 H5 NO2
Q119.
Q120. Choose the best synthesis of phenyl n-propyl ether
Q121.
Q122. What is true for the equilibrium reaction?
(a) The use of equimolar quantities of CH3 OH and CH3 COOH will give the greatest yield of the ester
at equilibrium
(b) Removal of water will increase the amount of ester at equilibrium
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FEAT 34 Alcohol, Ether and Epoxide
(c) Addition of CH3 COOCH3 will cause the formation of equal an equal number of moles of water
(d) Application of pressure increases the amount of ester at equilibrium
Q123. PCC (Pyridinium chloro chromate) is a good reagent for which of the following transformations?
Q124. How many primary alcohols (including stereoisomers) are possible with formula C5 H12 O ?
(a) Two
(b) Three
(c) Four
(d) Five
Q125. 1-Phenylethanol can be prepared by the reaction of benzaldehyde with the product obtained in the
reaction between:
(a) CH3 I and Mg
(b) C2 H5 I and Mg
(c) CH3 Br and AlCl3
(d) CH3 OH and ZnCl2
Q126. 0.092 g of a compound with the molecular formula C3 H8 O3 on reaction with an excess of CH3 MgI
gives 67.00 mL of methane at STP. The number of active hydrogen atoms present in a molecule of
the compound is :
(a) one
(b) two
(c) three
(d) four
Q127. Migratory aptitude of the following in decreasing order is:
(a) a > c > b > d
(b) a > d > b > c
(c) a > d > c > b
(d) b > c > a > b
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FEAT 35 Alcohol, Ether and Epoxide
Q128. Which of the following reactions is not exothermic?
Q129. Reaction of 𝑅-2-butanol with 𝑝-toluenesulphonyl chloride in pyridine then LiBr gives :
(a) R-2-butyl bromide
(b) 𝑆-2-butyl tosylate
(c) R-2-butyl tosylate
(d) S-2-butyl bromide
Q130. Optically active 2-octanol rapidly loses its optical activity when exposed to :
(a) dilute acid
(b) dilute base
(c) light
(d) humidity
Q131. If (±) 2-methyl butanoic acid were esterified by reaction with (±) 2-butanol, how many optically
active compounds would be present in the final equilibrium reaction mixture?
(a) 2
(b) 3
(c) 4
(d) 6
Q132.
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FEAT 36 Alcohol, Ether and Epoxide
Q133.
H3 O ⊕
Q134. (EtO)2 CHCHO + CH3 MgI ⟶ (𝐴)
Product obtained in the above reaction is:
Q135.
Q136.
Q137. this conversion can be achieved by
(a) O3 , Zn, then LiAlH4
(b) O3 /H2 O2 , then LiAlH4
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FEAT 37 Alcohol, Ether and Epoxide
(c) cold dil. KMnO4 , HIO4 , then LiAlH4
(d) All of these
Q138. Which of the following alcohol on treatment with HCl give 3-chloro-3-methyl cyclohexene as a
product?
Q139.
Q140. Esterification (shown below) is a reaction converting a carboxylic acid to its ester. It involves only
the carbonyl carbon. Esterification of ( )- -lactic acid with methanol yields (+)-methyl lactate.
Assuming that there are no side reactions, what is true about this reaction?
(a) AnSN2 process has occurred, inverting the absolute configuration of the chiral center
(b) AnSN1 reaction at the chiral center has inverted the optical rotation
(c) A diastereomer has been produced; diastereomers have different physical properties including
optical rotation
(d) Optical rotation is not directly related to absolute configuration, so the change in sign of rotation
is merely a coincidence
Q141. Which of the following sets of reagents, used in the order shown, would successfully accomplish the
conversion shown?
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FEAT 38 Alcohol, Ether and Epoxide
(a) CH3 CH2 CH2 MgBr; H3 O+ ; PCC, CH2 Cl2
(b) CH3 CH2 CH2 MgBr; H3 O+ ; H2 SO4, heat PCC, CH2 Cl2
+
(c) (C6 H5 )3 P − C̅HCH2 CH3 , B2 H6 ; CH3 CO2 H
+
(d) (C6 H5 )3 P − C̅HCH2 CH3 ; H2 O
Q142.
Q143. Which of the following compound on hydrolysis followed by heating gives a product, which gives
positive iodoform test?
Q144. Treatment of a 2∘ OH with CrO3 /H2 SO4 yields an/a :
(a) aldehyde
(b) carboxylic acid
(c) ester
(d) ketone
Q145. Esterification of the acid P with the alcohols Q will give:
(a) only one enantiomer
(b) a mixture of diastereomers
(c) a mixture of enantiomers
(d) only one diastereomer
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FEAT 39 Alcohol, Ether and Epoxide
Q146.
Identify major product of the reaction, when the given compound is hydrolysed and heated
strongly:
Q147. find out the reactivity order with LiAlH4 :
(a) 𝐴 > 𝐵 > 𝐶 > 𝐷
(b) 𝐵 > 𝐶 > 𝐷 > 𝐴
(c) 𝐷 > 𝐶 > 𝐵 > 𝐴
(d) 𝐵 > 𝐷 > 𝐶 > 𝐴
Q148. Find out the reaction in which obtained product give positive isocyanide test:
Q149.
In the above given compound how many functional group reduced by LAH (Lithium aluminium
hydride) and SBH (sodium borohydride) respectively?
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FEAT 40 Alcohol, Ether and Epoxide
(a) 4,4
(b) 4,3
(c) 3,4
(d) 4,2
Q150. An unknown compound (A) (molarmass = 180 ) on acylation gives a product (molar mass = 390 )
than find the number of hydroxyl group present in compound (A).
(a) 5
(b) 6
(c) 10
(d) 1
Q151. Which of the following compound is differentiated by NaHCO3 as well as by NaOH?
Q152. Arrange the following compounds in order of their reactivity toward LiAlH4 .
(a) i < ii < iii
(b) i < iii < ii
(c) ii < i < iii
(d) ii < iii < i
Q153. Choose the statement that is true about A,B and C in the following separation scheme
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FEAT 41 Alcohol, Ether and Epoxide
(a) 𝐴 = tetrahydroisoquinoline, 𝐵 = naphthalene and 𝐶 = inorganic ions such as Na+ and Cl−
(b) 𝐴 = naphthalene, 𝐵 = tetrahydroisoquinoline and 𝐶 = inorganic ions such as Na+ and Cl−
(c) 𝐴 = inorganic ions such as Na+ and Cl− , 𝐵 = naphthalene and 𝐶 = tetrahydroisoquinoline
(d) 𝐴 = inorganic ions such as Na+ and Cl− , 𝐵 = naphthalene and 𝐶 = tetrahydroisoquinoline
Q154.
(a) 2
(b) 3
(c) 4
(d) 5
Q155.
Q156. 1-Phenoxypropane is treated with excess of conc. HI at 0∘ C and the mixture of products is treated
with thionyl chloride. The products formed are
(a) n-propanol + Chlorobenzene
(b) Phenol +𝑛-propyl iodide
(c) n-propyl chloride + Chlorobenzene
(d) n-propyl chloride + Phenol
Q157. Amongst the following compounds, the compound having the lowest boiling point is
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FEAT 42 Alcohol, Ether and Epoxide
Q158. Which statement/s are true about products P & Q.
Q159.
Which of the following is/are possible end product of the above reaction?
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FEAT 43 Alcohol, Ether and Epoxide
ANSWERS - LEVEL 1
1. (c) 30. (c) 59. A-d 85. (b) 114. (b)
2. (a) 31. (b) 59. B-b 86. (c) 115. (b)
3. (b) 32. (b) 59. C − a 87. (c) 116. (d)
4. (c) 33. (a) 60. (c) 88. (b) 117. (b)
5. (b) 34. (b) 61. (c) 89. (d) 118. (a)
6. (b) 35. (b) 62. A-b 90. (a) 119. (b)
7. (b) 36. (c) 62. B-b 91. (c) 120. (a)
8. (a) 37. (c) 63. (b) 92. (b) 121. (a)
9. (b) 38. (c) 64. (c) 93. (b) 122. (b)
10. (b) 39. (d) 65. (b) 94. (a) 123. (b)
11. (b) 40. (c) 66. (a) 95. (d) 124. (d)
12. (b) 41. (b) 67. (a) 96. (b) 125. (a)
13. (a) 42. (b) 68. (d) 97. (c) 126. (c)
14. (a) 43. (d) 69. (a) 98. (a) 127. (b)
15. (a) 44. (d) 70. (c) 99. (c) 128. (c)
16. (a) 45. (b) 71. (b) 100. (a) 129. (d)
17. (d) 46. (a) 72. (d) 101. (d) 130. (a)
18. (a) 47. (b) 73. (d) 102. (b) 131. (c)
19. (b) 48. (b) 74. (c) 103. (c) 132. (b)
20. (a) 49. (a) 75. (b) 104. (c) 133. (c)
21. (a) 50. (b) 76. (d) 105. (d) 134. (b)
22. (a) 51. (a) 77. (c) 106. (c) 135. (a)
23. (d) 52. (c) 78. (c) 107. (b) 136. (c)
24. (a) 53. (c) 79. (d) 108. (a) 137. (d)
25. (b) 54. (c) 80. (c) 109. (c) 138. (d)
26. (b) 55. (b) 81. (c) 110. (d) 139. (b)
27. (b) 56. (a) 82. (d) 111. (c) 140. (d)
28. (b) 57. (d) 83. (a) 112. (b) 141. (c)
29. (c) 58. (c) 84. (b) 113. (b) 142. (b)
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FEAT 44 Alcohol, Ether and Epoxide
143. (b) 147. (b) 151. (c) 155. (a) 159. (d)
144. (d) 148. (a) 152. (d) 156. (b)
145. (b) 149. (d) 153. (b) 157. (c)
146. (c) 150. (a) 154. (b) 158. (𝑎, 𝑐)
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