//M0//QN1//SUB//DL0//EQ

Classify the following as primary, secondary and tertiary alcohols: (i) (ii) H 2 C = CH – CH 2 OH (iii) CH 3 – CH 2 – CH 2 – OH (iv) (v) (vi)

//X

(no answer)

//M0//QN2//SUB//DL0//EQ

Identify allylic alcohols in the above examples.

//X

(i) H 2 C = CH – CH 2 OH and
(ii)
Allylic alcohols in above example.

//M0//QN3//SUB//DL0//EQ

Give IUPAC names of the following compounds: (i) (ii) (iii) (iv) (v)

//X

(i) 3-Chloromethyl-2-isopropy pentanol
(ii) 2, 5-Dimethylhexane- 1, 3-diol
(iii) 3-Bromocyclohexanol
(iv) Hex-1-en-3-ol
(v) 2-Bromo-3-methylbut-2-en-1-ol

//M0//QN4//SUB//DL0//EQ

Show how the following alcohols are prepared by the reaction of a suitable Grignard reagent on methanal ? (i) (ii)

//X

//M0//QN5//SUB//DL0//EQ

Write structures of the products of the following reactions: (i) CH 3 – CH = CH 2 (ii) (iii)

//X

(i)
(ii)
(iii)

//M0//QN6//SUB//DL0//EQ

Give structures of the products you would expect when each of the following alcohol reacts with

(a) HCl - ZnCl 2 (b) HBr and (c) SOCl 2. (i) Butan-1-ol (ii) 2-Methylbutan-2-ol

//X

(a) With HCl-ZnCl 2:
CH 3 CH 2 CH 2 CH 2 OH + HCl reaction does not take place at room temperature.
Butan-1-ol
(b) With HBr:
CH 3 CH 2 CH 2 CH 2 OH + HBr CH 3 CH 2 CH 2 CH 2 Br + H 2 O
Butan-1-ol 1-bromobutane
(c) With SOCl 2:
CH 3 CH 2 CH 2 CH 2 OH + SOCl 2 CH 3 CH 2 CH 2 CH 2 Cl + SO 2 + HCl
Butan-1-ol 1-bromobutane

//M0//QN7//SUB//DL0//EQ

Predict the major product of acid catalysed dehydration of (i) 1-methylcyclohexanol and

(ii) butan-1-ol ?

//X

(i) 1-Methylcyclohexene
(ii) But-1-ene
CH3CH2CH2CH2OH CH3CH=CHCH3+H2O
But-2-ene (major)

//M3//QN8//SUB//DL0//EQ

Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of the corresponding phenoxide ions.

//X

The resonating structures of ortho and para nitrophenoxide ions are as below:
o-nitrophenoxide ion:
p-nitrophenoxide ion:
It can be seen that presence of nitro group increases stability of phenoxide ion.

//M2//QN9//SUB//DL0//EQ

Write the equations involved in the following reactions: (i) Reimer - Tiemann reaction (ii) Kolbe’s reaction

//X

(i) Reimer-Tiemann reaction:
(ii) Kolbe’s reaction:

//M0//QN10//SUB//DL0//EQ

Write the reactions of Williamson synthesis of 2-ethoxy-3-methylpentane starting from ethanol and 3-methylpentan-2-ol.

//X

C 2 H 5 OH C 2 H 5 Br

//M0//QN11//SUB//DL0//EQ

Which of the following is an appropriate set of reactants for the preparation of 1-methoxy-4-nitrobenzene and why? (i) (ii)

//X

In a first set double bond character is observed between C-Br bond due to resonance, which is difficult to break. Therefore, for the preparation of 1-methoxy-4-nitrobenzene set (ii) is more appropriate.

//M0//QN12//SUB//DL0//EQ

Predict the products of the following reactions: (i) CH 3 – CH 2 – CH 2 – O – CH 3 + HBr → (ii) + HBr → (iii) (iv) (CH 3)3 C – OC 2 H 5

//X

(i) CH 3 – CH 2 – CH 2 – O – CH 3 + HBr →
CH 3 CH 2 CH 2 OH + CH 3 Br
(ii)
(iii)
(iv) (CH 3)3 C – OC 2 H 5 (CH 3)3 C – I + C 2 H 5 OH