Solution Slot - 3 (Chemistry) Page # 141

Exercise - IV Subjective Type

1 i I2 + NaOH , ii WKR iii Zn/Hg-HCl iv LiAlH4 v N2H2

2 a NaBH4 b NaBH4 c Na + C2H5OH d LiAlH4

e H2–Pd/BaSO4 f NaBH4 g N2H2

OCH3 OCH3
| |
3 In acidic medium Me2 C  CH2 and in basic medium Me2 C  CH2
| |

OH O

4 a 1-hexanol reduces organ red CrO3 to green Cr3+; while 1-chlorohexane gives white ppt. of

AgCl on warming with ethanolic AgNO3.

b n-Butanol gives a positive test with CrO3 in acid and evolves H2 with

sodium; while dry ethyl ether is negative to both tests.

c Unlike n-pentane, diethyl ether is basic and dissolves in conc. H2SO4.

C2H52 O + H2SO4  C2H52 OH+ + HSO4–

5 i Mel + EtOH due to SN2 mechanism ii No reaction

4 LiAlH
6 i n-C3H7CO2H  
or B2H6
 n–H OH
9

OMgI
ii Me2CO + EtMgl  M2C H
 Me2COH Et
Et

IMgO Me

iii EtCO2Et + 2MeMgl  C H O

2 EtCMe2OH
Et Me

LiAlH MnO
iv 4
CHCO2Et    2
CHCH2OH    CHCHO

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 Page # 142 Solution Slot - 3 (Chemistry)

7 The +I.E. of three methyl groups on ce ntral C-atom of tert-butyl alcohol makes is partially
negative with the result that it pushes the electron pair of –OH bond towards H-atom and
thus H-atom is not replaced easily.

CH3 H
 
CH3 C O H CH3–CH2–CH2 C O H

CH3 H
(less partial + ve charge) (more partial +ve charge)

8 Oxygen atom is diethyl ether molecule has two ione pair of electron available for co-ordination.
Therefore ether behave as Lewis base forming oxonium salts.

R
O+HCl R2IO+Cl– (dialkyl oxonium chloride)
R

9 Due to formation of explosive peroxide by oxidation.

10 Ethanol being very weak Lewis base and thus reacts with stronger acid HI

11 i CH3CH2COOH ii CH3COOCH2CH2CH3

iii MePhSO2OCH2CH2CH3 iv PhCOOH + PhCOOCH2CH2CH3

O–CH2CH2CH3
v OH

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