Page 1 of 11 CPP - 2_AEP-PH-V

CPP - SHEET
ALCOHOL ETHER & PHENOL — SHEET - 2
OBJECTIVE

1. Which of the following pairs of the compounds can be used as starting materials in the synthesis of 2-phenyl-
2-pentanol?
(a) (CH3)3 CBr and PhCOOH (b) (CH3)2CHCH2Br and PhCOCH3
(c) PhBr and CH3CH2CH2COCH3 (d) PhBr and (CH3)2CHCH2COCH3

2. Which of the following alcohols can be synthesized using the reaction sequence?
O

Mg H3O
H3C Br 
ether
 
  

(a) H3C CH2CH2OH (b) HOH2C CH2CH2OH

(c) Br CH2CH2OH (d) H3CO CH2CH2OH

3. Choose the correct structure for the major compound produced by the following reaction sequence

NaNO2

HCl, 0o C


NH2
HO

(a) (b)
OH
O
HO

(c) (d)

HO
O

4. The increasing order of reactivity of the following towards acid catalyzed hydration is

(I) (II) (III)

(a) I  II  III (b) I  III  II

(c) II  I  III (d) III  II  I

5. A synthesis of 2, 5-dimethyl-2-hexanol from 2-methypropene requires the formation of X and Y. X and Y

combine to give the desired product after the usual hydrolysis work-up. Select appropriate methods of
preparing X and Y from 2-methylpropene.
(a) For X add HBr, then react with Mg in ether to 2-methylpropene, for Y add water, acid-catalysis 2-
methylpropene
(b) For X add HBr (peroxides), then react with Mg in ether to 2-methylpropene, for Y react with C6H5CO3H in
CH2Cl2 to 2-methylpropene
(c) For X add HOBr to 2-methylpropene, for Y add B2H6 in ether, then NaOH to 2-methylpropene
(d) For X add HOBr to 2-methylpropene, for Y add HBr (peroxides), then react with Mg in ether to 2-
methylpropene

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6. Which of the following will react with per iodic acid to give an aldehyde product?
OH

(A) (B)
OH
OH
O
(C) (D)
OH OH

7. The reaction that gives phenol is/are


Heat KOH H
(a)  conc. H2SO 4   
Fusion
 
H2O


NO2
NaNO2 KOH
(b) 
HCl; 0 C
  

300C HCl
(c) Cl  KOH   

 
H O2 H
(d)  CH3 — CH  CH2  
KOH
 


H2SO4 O2 H / H2O
8.  CH3 — CH CH2   P 
 h
 Q  R  S

Identify R and S.
O O H OH
O
(a) (b)
and and

OH OH
O
(c) (d) OH
and and

9. Which of the following is the best preparation of meta cresol, starting from toluene?
HNO3 Zn HNO2 H2O( v )
(a) 
H2SO4
 HCl
 
0 C
 
Br2 KOH HCl
(b) 
FeBr3
 
Heat
  

HNO3 (i) Zn / HCl HNO3 H HNO2 H3PO2 Zn HNO2 H2O( v )
(c) 
H2SO4

 
(ii) (CH3CO)2 O
 
H2SO 4

 
H2O
 
0 C
  
 
HCl
 
0 C
  
HNO3 (i) Zn / HCl HNO3 Zn HNO2 H2O(v )
(d) 
H2SO4
 
(ii) (CH3CO )2 O
 
H2SO 4

 
HCl
 
0 C
 

10. Which of the following reaction(s) gives mainly catchol (o-dihydroxy benzene)?
OH

NaOH H2O2 H3O
(a)  CHCl3   
NaOH
  

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OH

Zn NaNO2 H3O
(b) 
HCl
 
HCl / 0o C
  

NO2
NH2
HCl KOH
(c)  NaNO2 
0o C
 
aq


NH2
O
H2O
(d)  HBr  
O

11. Which of the following reaction will give a visible change?

OH

(a)
 Br2 — H2O 

OH

(b) CH3Cl
 NaOH(aq)  

N2Cl OH
(c)

OH
(d)  Conc. H2SO 4 

12. When phenol is reacted with CHCl3 and NaOH followed by acidification, salicylaldehyde is obtained. Which of
the following species are involved in the above mentioned reaction as intermediates?
O OH
H
CHCl 2
(a) (b)
CCl 2

O
O
H
CHCl 2
(c) (d)
CHCl

OH

13. Which of the following statements is correct?

i. Glycerol on reaction with oxalic acid at 110°C (383 K) and followed by heating and hydrolysis gives formic
acid and glycerol.
ii. Glycerol on reaction with oxalic acid at 230°C (503 K) and followed by heating gives allyl alcohol
iii. Glycerol on oxidation with dil. HNO3 gives a mixture of glyceric and tartonic acid.
iv. Glycerol on oxidation with conc. HNO3 gives glyceric acid
(a) i and ii (b) i and iii
(c) iii and iv (d) i, ii, iii, iv

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14. In the following compounds
OH OH OH OH
Me Me Me Me

Me Me Me Me

NO2 NO2

(I) (II) (III) (IV)

the order of acidity is
(a) (I) > (II) > (III) > (IV) (b) (I) > (II) > (IV) > (III)
(c) (II) > (I) > (III) > (IV) (d) (II) > (I) > (IV) > (III)

15. Which sets of reagents shown below would accomplish the following transformation?

OH
A

B

OH

A B
(a) BH3, H2O2/NaOH H2SO4
(b) H2/Pd/C BH3/H2O2/NaOH
(c) H3PO4 Hg(OAc)2; NaBH4
(d) EtOK BH3/H2O2/NaOH

SUBJECTIVE
1. Write the IUPAC name of the following compounds

H H H H NO 2

(a) H3C C C C C CH3 (b)

CH3 OH C2H5 OH OCH3

H3C CH2 C C OH
(c) (d) Benzylic alcohol
CH3 CH2OH

Cl

(e) CH3
H3C
OH

2. Write the IUPAC name of

(i) Isopentyl phenyl ether (ii) EtO OEt

O
O
(iii) (iv) Br

Br
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CH3 Ph
H3C
(v) (vi)
H O H O

3. Arrange the following compounds in the decreasing order of their boiling points and solubility in water.
(a) i) Methanol ii) Ethanol
iii) Propan-1-ol iv) Butan-1-ol
v) Butan-2-ol vi) Pentan-1-ol
(b) i) Pentanol ii) n-Butane
iii) Pentanal iv) Ethoxyethane
(c) i) Pntane ii) Pentane 1, 2, 3-triol
iii) Butanol
(d) i) Butane ii) Butanol
iii) Pentanol
(e) i) n-Butyl alcohol ii) sec Butyl alcohol
iii) t-butyl alcohol

4. Complete the following reactions—

i) CH3

H3C CH CH CH2 

(CH3COO)2 Hg
 NaBH4
 ?  
H2O

ii) CH3 CH  CH2  B2H6  ? H2O2

 
OH
iii) Cu Zn
CH3 CH  CH2  CO  H2  
H2

iv) H2O
H3 C  H2C  CH2NH2  HNO2  

5. Synthesize the following:

(a) Butene to butanol and butan-2-ol
(b) 1-chlorobutane to pentanol and pentan-2-ol
(c) Benzene to 3-(4-chlorophenyl) propanol
(d) Ethyne to butanol
(e) Propane to allyl alcohol

6. Complete the reaction:—

i) C2H5OH + NaNH2  ii) C2H5OH + RC  C–Na+ 
iii) C2H5MgBr + C2H5OH  iv) C2H5OH + NaOH 
v) CH3OH + NaOH  vi) CH3COOH + NaOH 
vii) C6HOH + NaOH 
viii) C—C—C—OH + Na 
SOCl2

PCl5
 
ix) C2H5 OH
PCl3
 
HCl
 
523 K
 
x) Al2O3
C2H5OH  
623 K
 

7. Identify A to E in the following sequence of reaction.

SOCl2
A(C4H10O)  B(C4H9 Cl)

O3 HCl
F  D(C3H6 O2 ) 
H2O2
 C(C4H8 )   E(C4H9 Cl)

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8. Write equations to show a combination of reactants to prepare each ether. Which ethers can be prepared in
good yield by a Williamson ether synthesis? If there are any that cannot be prepared by the Williamson
method, expain why not?

(a) (b)
O O
OMe

(c) (d)
O

9. a) Prepare the following ethers via Williamson’s synthesis.

I. Di-n-propyl ether (A)
II. Benzylmethyl ether (B)
III. Phenylethyl ether (C)
IV. t-Butyl ethyl ether (D)
b) Which compound in the above problem can be prepared by alternative Williamson’s reaction?
c) Explain the inability of (A), (C), and (D) in the above problem to be prepared via alternate Williamson’s
synthesis.
d) Give six types of ether that cannot be synthesised by the typical Williamson’s synthesis.
e) Rank the following alkyl halides in the decreasing order of reactivity in Williamson’s reaction.
(i) (CH3)3C—CH2Br (ii) ClCH2—CH = CH2
(iii) ClCH2CH2CH3 (iv) CH2CH2Br

10. a) An aromatic compound (A) (C7H8O) on reaction with Br2 + H2O gives a white ppt. of compound (B)
(C7H5OBr3). Compound (A) is souble in NaOH.Compound (C), an isomer of (A), also gives the same
reaction and gives a white ppt. of compound (D) (C7H5OBr3). Compound (C) is insoluble in NaOH. Identify
(A),(B), (C) and (D).
OH
b) 4-Chlorobutanol   (A)  (B)  Cl
conc. H2SO4
c) HOCH2—CH2—CH2—CH2OH 
160170o C


11. Provide structure of the compounds A to E in the following reaction

HOCl
(a)   A  B

(b) PhOMe + IH  C
ClH
(c)  D
O
ClH
(d)  E
O CH3

12. When C2H5ONa reacts with 1-(chloromethyl)oxirane, labelled with *C as shown by asterisk in I, the major
product is an epoxide bearing the labelled carbon as shown in II. Provide mechanism to explain this fact.
Cl
EtONa OEt
 
O O
I II
13. Predict products of the following reaction.
a) CH3OCH2CH2CH2CH3 + HI 
Cold
b) (CH3)3COCH2CH3 + HI  
O
c)  IH 

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14. Explain the following observations
a) When p-iodotoluene is treated with NaOH (aq) at 340°C, there is obtained a mixture of p-cresoland m-
cresol, with former in slightly greater amount, however at 250°C, reaction occur at slower rate andonly p-
cresol is formed.
b) When 1.0 ml of following compound is treated with 1.0 mol of aqueous KCN in hot condition, fluorine is
substituted mainly.
NO2

Cl F

NO2

15. Identify the lettered compounds in the following synthetic road maps:
OH
KOH
 HBr A(C8H9 OBr)   B(C 8H8O)
I) Inso lub le in NaOH(aq)

OH
OCH3

Mg
 HBr  C (C9H11OBr) 
Ether
 D(C18H22O2 )
II)

HC CH2

Heat
D  HBr   E(C16H18O 2 )

16. Give one test to distinguish between the following

i) CH3OH and C2H5OH
ii) n-propyl alcohol and isopropyl alcohol
iii) n-Butyl alcohol, sec butyl alcohol and tertbutyl alcohol
iv) Ethyl alcohol and Phenol

17. How are the ethers distinguished from

(a) (I) PhOH (II) CH3COOH
(b) (II) PhOMe (II) PhCH2OH
OH OH
O 2N NO2 Me Me
(c) (I) (II)

NO 2 Me
COOH COOH
OH OCOCH3
(d) (I) (II)

OH

(e) (I) PhOMe (II)

Me

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18. Suppose you were given unlabelled bottles, each of which is known to contain one of the following
compounds 1-pentanol, 2-pentanol, 2-methyl-2-butanol, 3-penten-1-ol, 4-pentyn-1-ol, 1-butoxybutane. Explain,
how you could use simple chemical tests.

19. Compounds X and Y both have the same molecular formula C4H8O, and they give the following results with
some characteristic tests:
Test  Compound X Compound Y
Bromine Decolourize No reaction
Na Metal Bubbles No reaction
Chromic acid Orange to green No reaction
Lucas reagent No reaction No reaction
What are the possible structures for X and Y?

20. An organic compound A (molecular formula, C6H12O) doesn’t decolourise the Bayer’s reagent and, doesn’t
change the colour of acidic dichromate solution. Compound A on treatment with H2SO4 produces alkene,
which on oxidative ozonolysis gives a molecule (C6H10O), Which gives the positive iodoform test. Find the
molecular structure of A.

21. A compound (a) has molecular formula C7H8O. It reacts with Na and NaOH and gives violet colour with FeCl3,
but doesn’t decompose NaHCO3. Upon oxidation A gives B which reacts with Na, NaOH, NaHCO3 and gives
violet colour with FeCl3. A on nitration gives mononitroderivative. The molecular structure of A is

——
ANSWER KEY
OBJECTIVE
1. C
2. A
3. D
4. A
5. B
6. B
Vicinal diol undergo periodic acid cleavage to give carbonyls.
7. A, C, D
8. C
9. C
10. A, B, C, D
11. A, C
12. A, D
13. D
14. C
15. C
SUBJECTIVE

CH3 H H CH3 H H

4. i) H3C CH3 NaBH4

  H C C C H

OH HgOCOCH3 CH3 OH H

H H

ii) H3C C C B 

–
H2O2 / OH
 H3 C — CH2 — CH2OH  H3BO3

H H 3

iii) CH3CH2CH2CH2OH + (CH3)2CHCH2OH

OH
iv) OH  H3C
H3C
CH3
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H H H
(1) BH3
C — C — C  C 
(2) H2O 2 /H
 H3C C C C OH

H H H
5. a)
H H
(1) Hg (OAc)2 / H2O

(2) Na BH4
 H3C C C CH3

H OH (1) BH3
C — C — C  C  
(2) H O /H 2 2

OH

b) C C (1) Mg/ Et 2O C C OH 

(2) HCHO
 (1) H / 
  H3C CH3
C C Cl (3) H2O /H  C C C (2) Hg(OAc)2 / H2O
(3) NaBH4

CH3 CH2Br CH2-CH2-CH2OH

(1) CH3Cl/ AlCl3 NBS (1) Mg /Et 2O

c) 
(2) Cl2 /Fe
   
O

(2)

(3) H2O / H

Cl Cl Cl

(1) NaNH2 (1) HB3 / THF

d) H — C  C — H 
(2) C H Br
 C  C — C2H5 
( 2) H O / OH
 1bu tan ol

2 5 2 2
(3) H2 / Pd

(1) Br2 /H (1) NBS

e) C — C — C  ( 2) Alc. KOH
 C  C — C 
(2) Aq. NaOH
 C  C — C — OH
6. i) C2H5ONa + NH3
ii) RC  CH + C2H5ONa
iii) C2H6 + Mg(OC2H5)Br
iv) No reaction
v) No reaction
vi) CH3COONa + H2O
vii) C6H5ONa + H2O
viii) C—C—C—ONa + H2
ix) C2H5Cl + SO2 + HCl
C2H5Cl + POCl3 + HCl
C2H5Cl + H3PO3
C2H5Cl + H2O
x) (C2H5)2O; C2H2
7. A 1-butanol B 1-chlorobutane
C 1-butene D Propanoic acid
E 2-chlorobutane F Formic acid
Na  Pr Pr
9. a) i) nPr—OH   nPr O  Pr— O — Pr
Repeat same steps for all the remaining reactions
b) The reaction only work with alkyl halide or alkyl sulphonate is primary or methyl
d) R2CHOCHR2; R3CO—CR3, Ar—O—Ar etc.,
e) ii  iv  iii  i

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10. (a) OH OH
Br Br
Br2 / H2O
 

CH3 CH3
Br
(A)
(B)

O CH3 OCH3
Br Br
Br2 / H2O
 

Br
(C)
(D)
(b) O
Cl  Cl Cl 

HO
OH
  O  
(A) (B)
(c)
O

11. (a)
Cl OH HO OH
(A) (B)
(b) PhOH + CH3I(C)
Cl
(c) HO (D)
Cl
(d) HO
CH3 (E)
12. ???
13. a) CH3I + CH3CH2CH2CH2I
b) (CH3)3Cl + C2H5I
c) 2-(3-iodopropyl) Phenol

14. (a) At 340°C, reaction follows elimination-addition mechanismwhile at 250°C, reaction follow addition-
elimination mechanism.
(b) NO2 group activate substitution of F by resonance effect.
OH
Br Br
15.

Br
16. i) Iodoform test
ii) Luca’s Test
iii) Luca’s Test
iv) Iodoform test
17. a) bicarbonate test
2–
b) benzyl alcohol, 1° ROH, is oxidised by Cr2O7 and the colour changes from orange to green, whereas the
other does not react.
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c) (I) (2, 4, 6-trinitrophenol or picric acid) is much more acidic, dissolves in aqueous NaHCO3 but (II) (2, 4, 6-
trimethyl phenol), much less acidic,does not dissolve.
d) (I) (salicylic acid) has a free phenolic (OH) and gives intense colour with neutral FeCl3, whereas (II) (acetyl
salicylic acid or aspirin) does not give this test.
e) (II) (p-cresol) is soluble in NaOH and also gives deep colour with netural FeCl3, whereas (I) (anisole, an
ether) does not dissolve.
18. 4-pentyn-1-ol can be distingushed by reaction with NaH. Using bromine water test 3-penten-1-ol can be
distinguished from other, between the 3 alcohols i.e., primary, secondary and tert alcohols luca’s test can be
used.
O
O
or
19. X can be C = C— C —C—OH & Y can be
OH

20.

CH3
21. OH

CH3

——

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