TARGET IIT JEE 2014

CHEMISTRY

ALCOHOLS
Single correct answers :
1
1. The relative rate of acid catalysed dehydration of following alcohols would be,

(A) III > I > IV > II (B) III >IV > I > II (C) I > III > IV > II (D) III > IV > I > II

2. Which of the following alcohol will show positive iodoform test

OH OH
| |
(A) CH3  CH  CH2  NO 2 (B) CH3  CH  CH2  COOH

OH
|
(C) ICH2  CH  CH2  CH3 (D) none of these

3. In the given reaction ,

B H , THF H O , NaOH TSCl t BuO ¯ K 

2 
6
 2 2        (Y)

The product ‘Y’ is

(A) A positional isomer of X
(B) Identical to X
(C) Chain isomer of X
(D) An oxidation product of X.

4. Which of the following reaction does not involve formation of an ether.

(CH3COO)2 Hg NaBH4
(A) CH2 = CH2 + C2H5OH       (B) CH N
2 2
 

(CH ) SO , NaOH KOH

(C)  3 
2
4  
 (D) (CH3)3CCl + C2H5 .OH  


Alcohol
5. The most appropriate major product of the following sequence of reactions would be.

H O
3 


(A) () (B) ()

(C) () (D)

6. The best yield of product ‘X’ can be obtained by using which one of the following sequence of
reagents and reactants.
,

OH
|
X = CH3 – C  C – CH – CH (CH3)2
NaNH (CH ) CHCHO H3O
(A) CH3 – C  CH   
2   32    

OH
| NaNH2 CH3
(B) (CH3)2CH – CH – C  C – H   
  


(C) CH3 – C  C – CH – CH2 – CH3 NaNH2 CH3

  
  

|
OH
OH
|
CH3Mg  CH3
(D) (CH3)2CH – CH – C  C – H     


7. What is the major product of the following sequence of reactions ?

3 PBr Mg
(CH3)2CHCH2OH    
 ?
OH OH
| |
(A) (CH3)2 CHCHCH2CH3 (B) (CH3 )2 CHCH2 CHCH3
(C) (CH3)2CHCH2CH2OH (D) (CH3)2CHCH2CH2CH2OH

8. The reaction of 3-butene-2-ol with aqueous HBr gives

(A) 3-bromo-1-butene only (B) 1-bromo-2-butene only
(C) a mixture of 3-bromo-1-butene and 1-bromo-2-butene (D) 4-bromo-1-butene

CH OH H O18
9.
3
B    2 
 A, A & B are
CH3O ¯ Na H

Alcohol
 CH3 CH3 CH3 CH3
| | | |
(A) CH3  C  CH2 CH3  C  CH2 (B) CH3  C  CH2 CH3  C  CH2
| | | | | | | |
18 OH OCH3 OH18 OH
OH OH OH OCH3
(C) both are correct (D) none is correct
10. The final major product of the following reaction is

conc . H SO 4 3 2( CH CO ) O
4 OH KMnO 
  2   A     B     C
BF3 

(A) (B) (C) (D)

H (dry HCl)
11.  A    
+ CH3CH2OH     B
dry HCl

(A) B is (B) B is

(C) B is (D) B is

5PCl Mg / ether 2 H O O ,
12.          2 (X), compound X is

(A) D-2-Butanol (B) L-2-Butanol (C) Both A & B (D) Nither A nor B

SOCl
2 Mg
13.       Product
pyridine,  ( C2H5 )2 O

Product of the reaction is

(A) (B)

(C) (D)

Alcohol
14. (Y) product

Compound Y is

(A) (B) (C) (D)


15. + X H

Write the structure of X

(A) (B) (C) (D)

MeOH
16. CH 2  CH  CH  CH  CHMe   CH  CH  CH  CH  CH  Me
H2SO 4 2
| |
OH OMe
H
|
(A) CH2  CH  CH  CH  C  Me (B) CH2 = CH – CH = CH – CH2 – CH2 – O – Me
|
O  Me

CH2  CH  CH  CH  CH  CH3 CH2  CH  C  CH  CH2  CH3

(C) (D)
| |
O  Me O  Me

17. H



(A) (B) (C) (D)

H
18. 

H2O

(A) (B) (C) (D)

19. H



(A) (B) (C) (D)

Alcohol
 CH CH OH
3
20.   2
H2SO 4

(A) (B) (C) (D)

OH
|
H2SO 4
21. CH3  CH2  C  C  CH  
|
CH3

O H O
|| | ||
(A) CH3 CH  C  CH2  C  H (B) CH2  CH  C  CH2  CH
| |
CH3 CH3

O O
|| ||
(C) CH3 CH  C  C  CH3 (D) CH3  CH  C  C  CH3
| | |
CH3 CH3 H

22.

(A) (B) (C) (D)

23.

(A) (B) (C) (D)

24. Compound ‘A’ has following solubilities in different solvents :

Which solvent would you prefer for recrystallization of that compound ?

Solubility (g / 100 g)
S.No. Solvents
20°C 80°C
1 Water 0.15 0.27
2 Ethanol 0.70 8.2
3 Benzene 16 38
4 Heptene 36 41

(A) 1 (B) 2 (C) 3 (D) 4

Alcohol
25. When (A) (given below) reacts with HI product is (B) and not (C). Explain.
HI HI

 


Br
2
26.   X
CH3NO2

(A) X is (B) X is (C) X is (D) X is


H
27. CH3 – CH2OH + CH2 = C = O  ?
(A) CH3  O  CH2  C  CH3 (B) CH3  CH2  C  O  CH3
|| ||
O O

(C) CH3  O  CH2  CH2  C  H (D) CH3  CH2  O  C  CH3

|| ||
O O

Answers
EXERCISE - 1
1. A 2. C 3. A 4. D
5. C 6. A 7. D 8. C
9. A 10. B 11. C 12. B

13. B 14. A 15. B 16. A

17. C 18. B 19. D 20. A
21. C 22. B 23. C 24. B
25. C 26. A 27. D

Alcohol
Find the correct answers in the following reactions : (More than one anwers may be correct)
2
conc . H SO 3O OH¯
1.   2 
4
 ( A ) 
  (B)  
 (C)
C9H16 (C9H16 O 2 ) (C9H14 O)

[(B) gives positive iodoform test.]

(A) A is (B) B is (C) C is (D) C is

PBr
3 Mg / Et 2O
2.    (A)     (B) (C)

(A) A is (B) B is

(C) C is (D) C is

K Cr O , H SOCl
3. 2 27  2
   X+Y

O
||
(A) X is Cl  C  C  CH2 Cl (B) X is
||
O

(C) Y is (D) Y is ClOC  C  CH3

||
O

Conc . H SO
4.   2
4
 A+B

(A) A is (B) A is (C) B is (D) B is

Alcohol
 CrO (i) CH MgI H SO , 
3 ( ii) BH , THF
5. 3
 
 3
 A    B 2  
4
 C     D
H2SO 4 (ii) H3O ( ii) H2O 2 , OH ¯
acetone

(A) A is (B) B is (C) B is (D) C is

H SO 4 LiAlH
6. 2 
4
 (A)    (B)

(A) A is (B) B is (C) A is (D) B is

7. (A) (B) (C)

(A) B is CH3  CH  CH2 C  CCH3 (B) B is CH3  CH2  CHC  CCH3

| |
O  CH3 OCH3

(C) C is CH3  CH  CH2  CH  CH  CH3 (D) A is

|
O  CH3

Conc. HI
8.  


(A) D is (B) C is (C) Bis (D) A is

9.

(A) E is CH3CH2CH2OH (B) D is CH3 – CH = CH2

(C) B is CH3CH2 – Cl (D) F is CH3  CH  CH3
|
OH

Alcohol
 HCl NaHCO 3 CrO3 / Py / CH2Cl2
10. (A)  (B)    (C)      (D)
HO 2

(A) A is (B) A is (C) B is (D) C is

11. Identify of the missing compounds in the following reaction sequences.

Br
CH2 = CH – CH2Br A 2
  B
C 4H8 O C4H8Br2O

KOH C

Heat C4H7BrO

(A) A is CH2 = CH – CH2CH2OH, (B) B is CH2  CH  CH2  CH2OH

| |
Br Br

(C) C is (D) C is

12. Identify the products in the following sequence of reactions.

(A)

(B)

(A) A is (B) B is

(C) C is (D) E is

Alcohol
13. Study the following road map of reactions. Identify unknown compounds mentioned in various
steps.

(A) Z is (B) J is

(C) C is Hg+2 / H2SO4 (D) K is

TsCl NaBr
14.   A 
 B
Pyridine

(A) A is (B) B is (C) A is (D) B is

15.

(A) (B) CH3 – O – H (C) (D)

Answers
EXERCISE - 2
1. A, B, C 2. A, B, C, D 3. B, D
4. B, C 5. B, C, D 6. A, B
7. A, C, D 8. A, B, C, D 9. A, B, C, D
10. B, C, D 11. A, B, C 12. B, C, D
13. A, B, C, D 14. A, B 15. A, B

Alcohol
One or More than one correct answers :
3
1. Alcohol A (C10H18O) is converted to a mixture of alkenes B and C on being heated with KHSO4.
Catalytic hydrogenation of B and C yields the same product. Assuming that dehydration of alcohol
A proceeds without rearrangement. Alkene B by ozonolysis forms cyclopentanone.
Identify correct options.
(A) A is (B) B is (C) C is (D) C is

2. An optically inactive organic compound A (C7H11Br) is treated with Mg in ether to give B (C7H11MgBr),
which react violently with D2O to give C. Reaction of B with acetone followed by hydrolysis gives

D(C10H18O). Heating D with concentrated acid gives . Identify correct options

(A) A is (B) B is

(C) D is (D) D is

3. A compound ‘A’ C9H10O exist in diastereomeric form, liberates a gas on reaction with CH3MgBr.
Treatment of A with aqueous HBr gives B (C10H13Br), which exist in enantiomeric forms. B on
treatment with alcoholic solution of KOH gives a compound C. Ozonolysis of C followed by work
up with H2O gives CH3CHO and Ph  CO  CH3 . Identify correct options
(A) A is Ph  CO  CH2  CH3 (B) A is Ph  CH2  CO  CH3
(C) B is Ph  (CH3 )C  CH  CH2  Br (D) C is Ph  (CH3 )C  CH  CH3
4. A compound X (C14H14O) on mild oxidation yields C14H12O(Y). If X is treated with a dehydrating
agent, it loses a molecule of water and resulting product on vigorous oxidation yields two
molecules of benzoic acid. Identify structures of X and Y.
(A) X is PhCH2CH(OH)Ph (B) X is Ph  (OH)CH  CH2  Ph
(C) Y is Ph  CO  CH2  Ph (D) Y is Ph  CH2  CO  Ph

5. Two optically active alcohols A and B have same molecular formula C9H12O and do not decolourise
bromine water solution. Both A and B are oxidised by KMnO4 to give benzoic acid and react with
Na to give a colourless odourless gas. Compound A gives yellow ppt with I2 / NaOH where as B
does not. Also A loses optical activity on oxidation but B does not. Identify structures of A & B.
H
|
(A) A is C 6H5  CH2  CH  CH3 (B) A is C 6H5  C  CH2CH3
| |
OH H  O
H
|
(C) B is C 6H5  CH  CH2  OH (D) B is C 6H5  C  CH2  CH3
| |
CH3 CH3

6. Compounds A, B and C are isomeric alcohols with formula C5H12O. A on oxidation gives ketone,
B gives acid while C is not oxidised A gives test with I2 / NaOH. The three isomeric alcohols react
with HBr with decreasing relative rates C > A > B. Identify A and B. A has 4 diastereomeric form B
with Al2O3 /  give optically active compound D.
(A) A is (CH3 )2 CH  CH(OH)  CH3 (B) A is (CH3 )3  C  OH
(C) B is (CH3 )2 CHCH2 CH2OH (D) B is (CH3 )2 C(OH)CH2 CH3

Alcohol
7. A neutral compound on acid hydrolysis produces two compounds B

(C4H8O) and C (C6H10O2). B on treatment with SOCl 2 gives D (C4H7Cl) which on further
treatment with aqueous solution of KCN followed by hydrlysis of product yielded ‘t’ (C5H8O2). E on
reducing with LiAlH4 gives F (C5H10O). Which on heating with conc. sulphuric acid solution yields

G (C5H8). G on treatment with HCl yields. . Identify correct options.

(A) C is (B) F is (C) E is (D) D is

8. A 3° optically active alcohol C9H18O ‘A’. On dehydration with conc. H2SO4 produces B (C9H16) which
exists in two stereomeric forms. Ozonolysis of B followed by work up with Zn – H2O produces
ethanal and C (C7H12O). C on treatment with LiAlH4 produced D (C7H14O). D on dehydration

produced . Identify the correct options.

(A) A is (B) A is

(C) D is (D) D is

9. An optically active alcohol A (C8H16O) on oxidation gives B. A on heating in acid gives C (C8H14) as
O
||
major product. C on ozonolysis produces D (C5H8O) and CH3  C  CH3 . D on reduction with

LiAlH4 gave . Identify the correct options.

(A) D is (B) C is

(C) B is (D) A is

10. Compound A is an optically active alcohol. Treatment with oxidising agent convert it to a ketone B.
In a separate reaction A is treated with PBr3, converting it into C. C on reaction with Mg is added to

B to yield . Identify correct options

(A) A is 2-butanol (B) A is 1-butanol (C) C is 2-bromobutane (D) C is 1-bromobutane

11. C7H14 (A) decolourises Br2 in CCl4 and reacts with Hg(OAC)2 in THF followed by reduction with
NaBH4 to produce a resolvable compound B. A undergoes reductive ozonolysis to give

as one of the compounds. Identify A and B.

(A) A is (B) A is (C) B is (D) B is

Alcohol
12. Compound A (C7H11Br) reacts with Mg in ether to give B. To this solution acetone (propanone) is
added slowly. When this solution is added to water a product C (C10H18O) is obtained. C on heating
with conc. H2SO4 gives D (C10H16). D on catalytic hydrogenation gives 2-methylpropylcyclohexane
(isobutylcyclohexane). If B is treated with water the product is E (C7H12) which on ozonolysis
produces 6-oxoheptanal. Identify the correct options.

(A) E is (B) D is

(C) C is (D) A is

13. An optically active compound A (C8H17Br) on heating with alcoholic KOH produces B (C8H16) as the
major product. B reacts with NBS (N-Bromo succinimide) and produces C (C8H15Br), another
optically active compound. Further dehydrobromination of C produces D (C8H14). When D is treated
with one mole of Bromine at 40° – 50°C, it forms an optically inactive dibromide E (C8H14Br2) as the
major product (80%). When E is added to an ethereal solution containing magnesium F (C8H14Mg2Br2)
is obtained. To this solution 1 mole of Ethyl acetate is added slowly and finally the product is
hydrolysed and identified as given bellow :

Identify the correct options.

(A) A is (B) B is (C) D is (D) E is

14. An alcohol (A) when heated with conc. H2SO4 gives an alkene (B). When (B) is bubbled through
bromine water and the product obtained is dehydrohalogenated with excess of sodamide, a new
compound (C) is obtained. The compound (C) gives (D) when treated with dilute H2SO4 in presence
of HgSO4. (D) can also be obtained either by oxidizing (A) with KMnO4 or from acetic acid through
its calcium salt. Identify the correct options.
(A) B is CH3 – CH = CH2 (B) C is CH3 – C  C – H
(C) A is CH3  C  CH3 (D) D is CH3  CH  CH3
|| |
O O H

15. A compound (A) gives Lucas test in 5 minutes. When 6.0 gm of (A) is treated with Na metal,
1120 ml of hydrogen is evolved at STP. Assuming (A) to contain one atom of oxygen per molecule,
write the structural formula of (A). Compound (A) when treated with PBr3 gives compound (B)
which when treated with benzene in presence of anhydrous AlCl3 gives compound (C). Identify the
correct options.

(A) C is (B) C is

(C) B is CH2  CH  CH2  CH2  OH (D) A is CH3 – CH = CH – CH2 – OH

| |
Br Br

16. An organic compound (A) composed of C, H and O gives characteristic colour with cerric ammonium
nitrate. Treatment of (A) with PCl5 gives (B) which reacts with KCN to form (C). The reduction of (C)
with warm Na/C2H5OH produces (D) which on heating gives (E) with evolution of ammonia. Pyridine
is obtained on treatment of (E) with nitrobenzene. Identify the correct options.

Alcohol
 (A) A is (B) C is

(C) D is (D) E is

17. Compound A (C6H14O) on reaction with Lucas reagent gives B. B on treatment with alc. KOH gives C.
(a) A has 3 more stereoisomers.
(b) B does not have any stereoisomer
(c) C has 1 more stereoisomer
Identify A, B, C and write the possible stereoisomers.What product A will give on treatment with
acetone and [(CH3)3C–O]3Al. Will it be optically active ?
(A) A is tope structure from answer at the back (B) B is draw structure of B
(C) C is draw structure of A (D) B is draw structure of B

18. Treatment of compound (A), C8H10O with chromic acid – pyridine gives (B), C8H8O. Treatment of
(B) with two equivalents of bromine yields (C), C8H6OBr, which on treatment with caustic soda
followed by acidification gives a compound (D), C8H8O3. The latter liberates CO2 on treatment with
NaHCO3 and is resolvable. Identify the correct options.

(A) A is PhCH2CH2OH / PhCHOHCH3 /

(B) B is PhCH2COH / PhCHOCH3 /

(C) C is PhCBrCHO
(D) D is PhCOCOOH

19. Three isomeric alcohol (A, B, C) (C5H12O) react with HBr with decreasing relative rates of
A > B >> C. B and C are oxidized by chromic acid solution, ‘C’ forms an acid in the oxidation
process. B is oxidized by NaOI. All three alcohol give the same product on treatment with HBr.
Identify A, B, C.
CH3 CH3
| |
(A) A is CH3  CH2  C  OH (B) B is HO  CH2  CH2  C  H
| |
CH3 CH3

CH3
|
(C) C is CH3  C  CH2  OH (D) A is CH3CH2CH2CH2CH2OH
|
CH3

20. An optically active compound (A) reacts with NaBr + H2SO4 Soln & gives an optically inactive
compound (B). A on reaction with CrO3 / aq. acetone gives a chiral compound C (C9H10O2). C on
reaction with moist Ag2O followed by treatment with Br2/CCl4 Soln gives D, a lower homologue of
B. A on heating with alkaline KMnO4 produces E (C7H6O2). A, C & E all liberate a Colourless &
odourless gas with Na metal. A does not respond to iodoform test . A on controlled oxidation with
CrO3– pyridine produces a chiral compound F. Identify the correct options.
(A) A is C 6H5  CH  CH2  OH (B) C is C 6H5  CH  COOH
| |
CH3 CH3
CH3
|
(C) E is C6H5 – CHO (D) F is C 6H5  CH  CHO

Alcohol
21. C7H14 (A) decolorize Br2 in CCl4 and reacts with Hg(OAc)2 in THF – H2O followed by reduction with
NaBH4 to produce a resolvable compound B. A undergoes reductive ozonolysis to give the same
compound obtained by oxidation of 3-hexanol with KMnO4 (C). Identify A, B and C.
(A) C is O  C  CH2CH2 CH3 (B) A is CH2  C  CH2CH2CH3
| |
C 2H5 C 2H5

(C) B is (D) B is

22. A compound ‘C’ on hydroboration oxidation gave . optically active (trans isomers). Compound A
which on reaction with TsCl gave compound B, which on treatment with NaI gave D and an opti-
cally active (trans isomer) D on treatment with aq KOH gave E (C5H10O) ± trans. If ‘C’ contains a
four membered cyclic ring having double bond equlvalent 2. Find the correct options.

(A) A is (B) D is (C) C is (D) E is

23. A cyclic ester on treatment with excess of CH3MgBr followed by treatment with NH4Cl / H2O give a

diol which on oxidation gave . Identify the correct options.

(A) (B)

(C) (D)

24. A (C5H12O) ether, on reaction with PCl5 forms alkyl chloride (B) and (C). (B) and (C) both on reaction
with aqueous KOH form alcohol (D) and (E) ; Both (D) and (E) give iodoform test. Identify the
correct options.

(A) A is (B) C is CH3  CHCH3

|
Cl
(C) C is CH3CH2Cl (D) E is CH3  CH  CH3
|
OH

25. Dehydration of 2, 2, 3, 4, 4-pentamethyl-3-pentanol gave two alkenes A and B. Ozonolysis of A

gave HCHO and 2, 2, 4, 4-tetramethyl-3-pentanone and that of B gave HCHO and
3, 3, 4, 4-tetramethyl-2-pentanone. Identify A and B and explain reaction.

CH3CH2CH3 CH3CH3 CH2

| || | | | ||
(A) A is CH3 C – C – CCH3 , (B) B is CH 3 C – C – C – CH3
| | | |
CH3 CH3 CH3 CH3

Alcohol
 CH3 CH3 CH2 CH3 CH2 CH3
| | || | || |
(C) A is CH3  C  C  C  CH3 (D) B is CH3  C  C  C  CH3
| | | |
CH3 CH3 CH3 CH3

26. Compound A (C11H16O) was found to be an optically active alcohol. Despite its apparent unsaturation,
no hydrogen was absorbed on catalytic reduction . On treatment of (A) with H2SO4, dehydration
occured and B, an optically inactive alkene (C11H14) was produced as major product. Alkene B on
ozonolysis gave two products C & D. The compound C (C3H6O) does not give iodoform test but
gives positive Tollen’s test. The compound D(C8H8O) gives positive iodoform test and on oxidation
gives a monobasic acid (E) C7H6O2. Identify A, B, C, D & E and explain reaction sequences.

(A) B is (B) C is CH3 – CH2 – CHO

(C) D is (D) E is

27. An unknown compound ‘A’ with the M.F C9H12O does not decolourize Br2 in CCl4 and is oxidized
by hot KMnO4 to give PhCO2H. The compound reacts with Na to give a colourless odourless gas.
Give five isomeric structures (A-E) fitting these data and from the following results deduce the
correct structure of (A).
(i) the colour of Cr2O72– changes from orange to blue green when added to A, B, C or D.
(ii) the compound can be resolved.
(iii) no ppt of CHI3 is observed with I2 / OH–.
(iv) oxidation with CrO3 /pyridine gives a chiral compound.

(A) A is (B) E is

(C) C is (D) D is

Answers
EXERCISE - 3
1. A, B, C 2. A, B, D 3. A, D

4. B, C 5. A, C 6. A, C

7. A, B, C, D 8. B, D 9. A, B, C, D

10. A, D 11. A, C 12. B, D

13. A, C 14. A, B 15. A, C

16. A, B, C, D 17. A, B, C, D 18. A, B, C

19. A, C 20. A, B, D 21. A, B, C

22. A, B, D 23. A, B 24. A, B, D

25. A, B 26. A, B, C, D 27. A, C, D

Alcohol
Assertion Reason type Question
4
(A) If both assertion and Reason is correct explanation of A
(B) If both assertion and Reason are correct but Reason is not correct explanation of A
(C) If assertion is correct, reason is wrong
(D) If assertion is wrong, reason is correct

1. Assertion : Esters are hydrolysed by acids or alkalis.

Reason : Alkaline hydrolysis is far more rapid than acid hydrolysis.

2. Assertion : Alkaline hydrolysis of esters is a second order reaction in BAC 2 mechanism.

Reason : Mechanism of the reaction is

3. Assertion : Acid catalysed hydrolysis and acid catalysed esterification are the reverse of each
other.
Reason : This is because of the principle of microscopic reversibility.

4. Assertion : Lucas reagent gives white turbidy immediately with tertiary alcohol.
Reason : With tertiary alcohol the reaction proceds by SN2 mechanism.

5. Assertion : The ease of dehydration of alcohol being 1° > 2° > 3°.

Reason : The acid catalysed dehydration of alcohol may be accompanied by rearrangement.

6. Assertion : Rearrangement often occurs in acid-catalysed dehydration.

Reason : Carbocation intermediate formed during dehydration may rearrange to get more stable
product.

7. Assertion : The oxidation of primary and secondary alcohols by dichromate and permangnate
ions involves an ester intermediate.
Reason : The rate determining step is the removal of hydrogen from the intermediate formed.

8. Assertion : (CH3)3C – Br and CH3CH2ONa will react and form only (CH3)3C – O – CH2CH3
Reason : Ethers are prepared by the reaction of alkoxides with alkyl halides.

9. Assertion : The boiling point of ethanol is much higher than that of diethyl ether.
Reason : In ethanol, the molecules are associated by the formation of intermolecular hydrogen
bonding whereas in diethyl ether it is not possible.

10. Assertion : Addition of C2H5OH to 3, 3-dimethyl-1-butene gives 2-ethoxy-2, 3-dimethylbutane in-

stead of 3-ethoxy-2, 2-dimethylbutane.
Reason : The reaction occurs by SN2 mechanism.

Alcohol
11. Assertion : On treatment with concentrated H2SO4, tert butyl alcohol does not give ditertiary butyl
ether ; instead it gives 2-methyl propene.
Reason : On reaction with concentrated H2SO4, tertiary alcohols do not give ethers due to the
instability of ethers formed in H2SO4 and also due to steric crowding.

12. Assertion : Some alcohols are poured in small quantity in the fuel tanks of automobiles, particu-
larly in cold countries.
Reason : The moisture present in gasoline gets dissolved in the alcohol, and therefore, does not
freeze.

13. Assertion : One being heated with n-butanol in the presence of sodium butoxide (n-C4H9ONa),
ethylacetate gives n-butylacetate.
Reason : In trans esterification the alkyl group of one ester is preplaced by the alkyl group of
another alcohol.

Answers
EXERCISE - 4
1. B
H O
Hint : R1CO2H + R2OH 3
 R1CO2R2

2. A

3. A
Hint : The mechanism of acid catalysed hydrolysis is the reverse of acid catalysed esterification.

4. C
Hint : Tertiary alcohol forms carbocation easily resulting in immediate reaction with Lucas reagent.

5. D
Hint : The ease of dehydration of alcohol is 3° > 2° > 1° which due to the stability of intermediate
carbocation which is formed.

6. A

7. B
Hint : The mechanism is
Cr2O7–2 + H2O 2HCrO4¯
Me2CHOH + HCrO4¯ + 2H+ Me2CH – O – CrO3H2+ + H2O
Me2CO + H3O+ + H2CrO3

8. D 9. A 10. C

11. A 12. A 13. A

Alcohol