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1. .

What type
of
isomerism
exists
between the
following
pairs of
compounds?
(i) Pentan-1-ol and 3-Methylbutan-1-ol
(ii} Ethanol and Dimethyl ether
(iii} Butan-1-ol and Butan-2-ol
(i) (ii} (ill}
(a} Chain Functional Position
isomerism isomerism isomerism
(b) Functional Chain Position
isomerism isomerism isomerism
(c} Position Chain Functional
isomerism isomerism isomerism
(d} Chain Position Functional
isomerism isomerism isomerism
,

C5H 12O is a
monohydric
alcohol. How
many isomers of
this alcohol are
possible? How
many of these
contain chiral
centres as well as
can exhibit
enantiomerism?

(a) 8 and 3
(c) 4 and 2

(b) 6 and 2
(d) 12 and 4 ,

2. 3-propylbutan-1-ol
3. 2-ethylpentan -1- ol
4. 3-methyl hydroxyhexane
5. 2-ethyl-2-propyl ethanol
.
A compound
C6H14O2 has two
tertiary alcoholic
groups . The IUPAC
name of this
compound is
6. 2, 3-dimethyl - I, 2-butanediol
7. 3, 3-dimethyl - I, 2-butanediol
8. 2, 3-dimethyl - 2, 3-butanediol
9. 2-methyl - 2, 3-pentanediol
/

Which of the following is phenol?


(a) Crcsol (b) Catechol
(c) Benzcnol (d) All of the,.

,

Classify the following as primary, secondary


and tertiary alcohols :

(i)
(ii) H2C= CH—CH2OH
(iii) CH3—CH2—CH2—OH (AI 2009

2. Wood alcohol is
(a) CH3OH (b) C2H5OH (c) CH3CH2CH2OH (d) (CH3)2CHOH <a>
3. Grain alcohol is
(a) CH3OH (b) C2H5OH (c) CH3CH2CH2OH (d) (CH3)2CHOH<b>
4. Rubbing alcohol is
(a) CH3OH (b) C2H5OH (c) CH3CH2CH2OH (d) (CH3)2CHOH<d>
5. Absolute alcohol is
(a) CH3OH (b) C2H5OH (c) CH3CH2CH2OH (d) (CH3)2CHOH<b>

Structures of Functional Groups:


The oxygen atom in alcohols and phenols is sp3 hybridised and
they have tetrahedral disposition of hybrid atomic orbitals. The
two hybrid atomic orbitals have lone pair of electrons and
remaining two are involved in bond formation. The value of 􀂑ROH bond angle depends upon the bulk of R
group and repulsion between lone pair of electrons on oxygen. Due to the lone pair – lone pair repulsion,
the C-O-H
bond angle in methanol is reduced to 108.9° from the regular tetrahedral bond angle of 109.5° .
In phenols, the –OH group is attached to sp2
hybridised carbon of an aromatic ring. The carbon– oxygen bond
length (136 pm) in phenol is slightly less than that in methanol. This
is due to (i) partial double bond character on account of the conjugation
of unshared electron pair of oxygen with the aromatic ring (Section
11.4.4) and (ii) sp2 hybridised state of carbon to which oxygen is
attached.
In ethers, the four electron pairs, i.e., the two bond pairs and two
lone pairs of electrons on oxygen are arranged approximately in a
tetrahedral arrangement. The bond angle is slightly greater than the
tetrahedral angle due to the repulsive interaction between the two
bulky (–R) groups. The C–O bond length (141 pm) is almost the same
as in alcohols.

Which of the following is dihydric alcohol ?


(a) Glycerol (b) Ethylene glycol
(c) Catechol (d) Resorcinol

An example of a compound with functional group – O – is :


(a) acetic acid (b) methyl alcohol
(c) diethyl ether (d) acetone
.
12. How many alcohol(s) with molecular formula C4H10O are
chiral in nature?
(a) 1 (b) 2
(c) 3 (d) 4 ,

/
/*
127. Match the columns
Column-I Column-II
(A) Antifreeze used in (p) Methanol
car engine
(B) Solvent used in (q) Phenol
perfumes
(C) Starting material for (r) Ethleneglycol
picric acid
(D) Wood spirit (s) Ethanol
(a) A – (s), B – (q), C – (p), D – (r)
(b) A – (r), B – (s), C – (q), D – (p)
(c) A – (s), B – (q), C – (r), D – (p)
(d) A – (p), B – (r), C – (q), D – (s) .

Assertion : The bond angle in alcohols is slightly less


than the tetrahedral angle.
Reason : In alcohols, the oxygen of –OH group is attached
to sp3 hybridized carbon atom.

138. Vinyl carbinol is


(a) HO 􀀐CH2 􀀐CH 􀀠 CH2
(b) CH3C(OH) 􀀠 CH2
(c) CH3 􀀐CH 􀀠 CH 􀀐OH
(d) CH3 􀀐C(CH2OH) 􀀠 CH2 ,

The C-O-C angle in ether is about


(a) 180° (b) 190°28' (c) 110° (d) IOS'

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