CHEMISTRY

Class

II IIT- JEE Achiever 2016-17

Intensive Revision Camp
Worksheet 16

Topic

Alcohols, Phenols and Ethers

Date

22-12-2016

Multiple choice questions with one correct alternative

1.

The major product of the following reaction is

(A)

(B)
CH3
OH

CH3

CH2OH

CH2OH

OH

(C)

CH3

(D)
CH3

OH

CH3
OH

2. Treatment of 3-methyl-2-pentanol with POCl3 in pyridine will provide

(A) a mono substituted alkene
(B) a disubstituted alkene
(C) a trisubstituted alkene
(D) a tetrasubstituted alkene
3. Which of the following alcohol will give the compound A the fastest upon treatment with H3PO4?

(A)

(B)

(C)

(D)

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4. Which of the following functional groups would form upon treatment A with PCC?

(A) Ketone

(B) Aldehyde

(C) Carboxylic acid

(D) Both (A) and (B)

5. Treatment of a with excess of HBr will provide?

(A)

(B)
Br

(C)

(D)
HO

HO

6. The major thermodynamic product of the reaction given below is

(A)

(B)

(C)

(D)

7. 3-phenyl-2-propanol could be prepared from, which of the following reaction?

(A)

(B)

(C)

(D)

8. Ethanol on refluxing with acetic anhydride in presence of acid catalyst gives

(A) acetic acid
(B) formic acid
(C) a cyclic acid
(D) ethyl ethanoate and acetic acid

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9. Which of the following reagent or set of reagents will best bring about the following reaction?

(A) H3O+
(C) NaOH/CH3I

(B) (i) POCl3 (ii) H+/CH3OH

(D) (i) H3PO4 (ii) NaBH4

10. Which of the following reagent or set of reagents will best bring about the following reaction?

(A) H3O+
(C) NaOH/CH3I

(B) (i) POCl3 (ii) H+/CH3OH

(D) (i) H3PO4 (ii) NaBH4

11. Which of the following reagent or set of reagents will best bring about the following reaction?

(A) H3O+
(B) (i) POCl3 (ii) H+/CH3OH
(C) NaOH/CH3I
(D) (i) H3PO4 (ii) NaBH4
12. Consider the following reaction of ethers with HI
(I)
Which of the above two reaction will produce a di-iodine if excess of HI is used?
(A) I and II both
(B) I only
(C) II only
(D) none of these

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13. Consider the following reaction scheme

A, B and C are respectively

(A) Hg(OAc)2/H2O/NaBH4 ; dil.H2SO4() ; B2H6/H2O2/HO
(B) dil.H2SO4() ; Hg(OAc)2/H2O/NaBH4 ; B2H6/H2O2/HO
(C) dil.H2SO4 () ; B2H6/H2O2/HO ; Hg(OAc)2/H2O/NaBH4
(D) B2H6/H2O2/HO ; Hg(OAc)2/H2O/NaBH4 ; dil.H2SO4()
14. There may be something seriously wrong with the following proposed synthesis of the drug terfenadine.
Identify the problem if any, and propose specific steps needed to make this route workable.

(A) There is nothing wrong

(B) In presence OH group, Grignard synthesis cant be carried out
(C) N will be involved in neighbouring group participation
(D) Both (B) and (C)
15. Which of the products shown below would be the principal product produced in the reaction of
benzylmagnesium bromide, PhCH2MgBr, with ethyl formate, CH3CH2OCH=O?
(A) PhCH2CHO
(B) PhCH2COOCH2CH3
(C) PhCH2CH(OCH2CH3)CH2Ph
(D) PhCH2CH(OH)CH2Ph
16. Select the method that could be used to prepare the compound shown below

(A)

(B)
(C)

(D)
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17.

(A)

(B)

(C)

(D)

18. The relative rates of reaction of each of the following with H2SO4

(A) i > ii > iii

(B) i > iii > ii

(C) ii > i > iii

(D) ii > iii > i

19. Major product of the following reaction is

(A)

(B)

(C)

(D)

20. Major product of the following reaction is

(A)

(B)

(C)

(D)

21. Which of the following ether could not be synthesized by a Williamson synthesis?
H3C

(A) HOCH2CH3

(B) H

H3C

(C)

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(D) CH3CH2O

CH3
H
CH3

22. When t-butyl methyl ether is prepared by the bimolecular dehydration of methanol,
H 2 SO4
(CH 3 )3 COH CH 3OH
(CH 3 )3 COCH 3 H 2 O
the reaction takes place, at least in part, via
(A) an SN1 reaction ; then methyl carbocation reacts with a molecule of t-butanol
(B) an SN1 reaction ; then t-butyl carbocation reacts with a molecule of methanol
(C) an SN2 reaction of a t-butoxide anion with a protonated methanol
(D) an SN2 reaction of a methoxide anion with a protonated t-butanol
Multiple choice questions with one or more than one correct alternatives

23. What are the expected products of the following dehydration reaction?

(A)

(B)

(C)

(D)

24. Methanol and ethanol can be distinguished by

(A) Heating with I2/NaOH
(B) Treatment with Schiffs reagent
(C) Treatment with H2CrO4
(D) Treatment with acidic KMnO4
25. Dehydration of alcohol with POCl2 occurs more rapidly than with H2SO4. Select the correct statement
about the following reaction

(A) it does not involve carbocation

(B) it involves ROPOCl2 with OPOCl2 as better leaving group
(C) it involves E2 mechanism
(D) it is a E1 reaction without carbocation
26. Which of the following combination of reagents can give 3-methyl-3-hexanol?
(A) CH3MgBr + 3-hexanone followed by hydrolysis
(B) C2H5MgBr + 2-pentanone followed by hydrolysis
(C) C3H7MgBr + butanone followed by hydrolysis
(D) C4H9MgBr + propanone followed by hydrolysis
27. Pick the correct statement

(A)

(B)

(C)

(D)

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28. Which of the following gives ether successfully?

(A)
(B) C2H5ONa + (CH3)2SO4
(C)
(D) (CH3)3CBr + C2H5ONa
29. In which of the following reactions, reactant and products are correctly matched?
(A)

(B)

(C)
(D) PhBr + (CH3)3CONa PhOC(CH3)3
30. Which is/are true regarding the following reaction?

(A) The product will be a single pure enatiomer

(B) The product will be a racemic mixture
(C) It involves nucleophilic addition reaction
(D) If D2O is used, CH3CH2CD(OH)CH3 is formed
31. Which of the following Griganard reaction will fail to occur as written?
(A)

(B)

(C)

(D)

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32. Consider the following reaction

The true statement about the above reaction is(are)

(A) The product will be a single pure enantiomer
(B) The product will be a recemic mixture
(C) The equilibrium constant of the above reaction is greater than one
(D) If H2O18 is used as solvent, both reactant and product will incorporate O18.
Read the passage given below and answer questions 33 and 35 by choosing the correct
alternatives

Consider the following reaction scheme to answer the next three questions

33. In the above reaction, [X] and A are respectively

(A) Hg(OAc)2-H2O/NaBH4 and

(B) BH3-THF/H2O2/NaOH

(C) H2SO4(dil.) and

(D) C2H5ONa and

34. Identity of B is
(A)

(B)

(C)

(D)

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35. Compound C and reagent [Y] are respectively

(A)

(B)

(C)

(D)

Read the passage given below and answer questions 36 to 39 by choosing the correct
alternative

Consider the following synthesis and the step involved to answer the next four questions

36. In the above reaction, the most likely A and B are respectively
(A)

(B)

(C)

(D)

37. Which of the following regarding stereochemistry of product is true?

(A) The product is chiral and a pure enantiomer is formed
(B) The product has two chiral carbon and a total four diastereomers are formed
(C) The product is chiral and a racemic mixture is formed
(D) The product is overall achiral
38. In the above synthesis, if the step involving treatment with HBr is skipped and rest of the synthesis is
carried out as such, the end product of the reaction would be
(A) the same product

(B) no product

(C)

39. In the above synthesis, X, C and Y are respectively

(A) conc.H2SO4, cyclohexene and m-CPBA
(B) SOCl2, chlorocyclohexane and KOH
(C) PCC, chlorocyclohexane and CH2N
(D) HCl, chlorocyclohexane and Cl2H2O

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(D)