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22.

ALCOHOLS, PHENOLS AND

ETHERS

ALCOHOLS

1. INTRODUCTION

(a)

These are the organic compounds in which -OH

group is directly attached with carbon. (b) These are hydroxyl derivatives of alkanes, mono alkyl derivatives of water. (c)

Their general formula is C

n H n+1

OH or C

n H 2n+2 O.

Mono, Di, Tri or Polyhydric Compounds

they contain one, two, three or many hydroxyl groups respectively in their structures as given below: 3 In this class of alcohols, the -OH group is attached to an sp 3 hybridised carbon atom of an alkyl group. They are

In these types of alcohols, the -OH group is

attached primary secondary and tertiary carbon atom, respectively as depicted below.

In these

alcohols, the -OH group is attached to an sp 3 hybridised carbon next to bond, i.e. to an allylic carbon. For example

Primary (1

o -CH-OHCH-OHC-OH-

Secondary (2

o )Tertiary (3 o

CH?CH-CH-OH

--C CH

CH-C-OHH

--C CH CHC-- OH

Seco)ndary (2

o

Tertiary (3

o )Primary (1 o C

22.2 | Alcohols, Phenols and Ethers

(c)

In these alcohols,

the -OH group is attached to an sp 3 -hybridized carbon atom next to an aromatic ring. For example Allylic and benzylic alcohols may be primary, secondary or tertiary 2 to a vinylic carbon or to an aryl carbon. These alcohols are also known as vinylic alcohols

Vinylic alcohol : CH

2

2. PREPARATION OF ALCOHOLS

C=CC-C+HO

H HOH H-

CHCHCH=CH+ HO-CH-CH

Alkenes react with water in the presence of acid as catalyst to form alcohol. In case of unsymmetrical alkenes, the

addition reaction takes place in accordance with Markonikov's rule. The mechanism of the reaction involves the following three steps: HO 2 +H HO 3

C=C+ H- O

H HC H C H 2 O C H C H 2 OC H C O H H C H CO H H+ H 2 O C H C OH HO 3

Step 1

Step 2

Step 3

Diborane (BH

3 2

reacts with alkenes to give trialkyl boranes as addition product. This is oxidized to alcohols in the

presence of aq. sodium hydroxide (NaOH) and peroxide. CHOH 2 H C C OHC C OH C

PrimarySecondaryTertiary

OHCH OH

Chemistry | 22.3

HC 3 -CH=CH 2 + (H-BH) 23
CH 3 -CH-CH 2 HBH 2 CH 3 -CH=CH 2 (CH-CH-CH) 3223
B CH 3 -CH=CH 2 (CH-CH-CH)BH 3222
HO 2

2HO, OH

22
CH 3 -CH-CH-OH + B(OH) 223

Proapn-1-ol

CH ?-CH CH CH -CHCHBH-THF/HO/OH CH -CH-CH-OH CH -CH-CH O. BH

CH-CH-CH

BH BH

H-transfer

These steps are repeated thrice to form (CH

3 - CH 2 - CH 2 3

B and then

RB R R

H O O

H RB R R -H+ OOHRB R R OOH -OH- RBOR R

With H

2 O 2 OR RO B OR is formed by above mentioned method. |3NaOH 33
OR

RONaB O3ROHB OR

Involves an electrophilic attack on the double bond by the positively charged mercury species. The product is a

(CH) 32

CHCH = CH

2

3-Methylbut-1-eneHg(OCOCH)

32
(CH) 32

CHCH-CH

2

OHHgOCOCH

3

Not-isolated

NaBH 4 (CH) 32

CHCHCH

3 OH

3-Methyl-1-butanol

22.4 | Alcohols, Phenols and Ethers

CCHg(OAc)CC

Hg OAc mercurinium ion

Mercuration commonly takes place in a solution containing water and an organic solvent to dissolve the alkene.

Attack on the mercurinium ion by water gives (after deprotonation) an organomercurial alcohol.

Hg(OAc)

Hg(OAc)

-C C--C C--C C- HO: HO:H +O:

Hg(OAc)Hg(OAc)

-H+ H

Organomercurial alcohol:OH

-C-C- OH -C-C-

OH+ NaBH4OH-+

+NaB(OH)4Hg + 4OAc alcohol

Organomercurial alcohol

H The second step is demercuration, to form the alcohol. Sodium borohydride (NaBH 4 , a reducing agent replaces the mercuric acetate with hydrogen.)

R-CHO + 2H

R-CH-H

O R-

C-R+2H

O LiAlH / Na + CHOH LiAlH / Na + CHOH OH 1 o alcohol

R-CH-R

OH 2 o alcohol

R - C - OH + 4H

O LiAlH

R-CH-OH

R - C - X + 4H

O LiAlH

R-CH-OH + HX

R - C - OR'+ 4H

O LiAlH LiAlH

R-CH-OH + R'OH

RCOOCOR + 8H2 RCHOH + HO

Chemistry | 22.5

R:MgX+H?C-CH?+

O

R-CH-CH-OMgX

R -CH-CH-OH

Primary alcohol

H O+

R : Mg X + C =

OR C O H + MgX?-

i) ether ii) HO, X

R : MgX + C =

OR C O MgX--

R C O MgX + H O

H---- H

R C O H + O H + MgX----

H Ether CH HCH CH H CHC

HHOCH-CH-MgBr+O

OMgBr OH butan-2-ol

EtherCH?

CH CH CH CH H? C H? C H? C H? O

CH-CH-CH-MgBr+OOMgBrOH

2-methylpentan-2-ol

Fermentation is a low decomposition of complex organic compounds into simpler compound in the presence of

6105n322233

Starchn Butylalcohol

(CH O) CHCH CHCH OH CHCO CH

22.6 | Alcohols, Phenols and Ethers

3. PHYSICAL PROPERTIES OF ALCOHOLS

(a) The lower alcohols are liquids while higher having more than 12 carbon atoms are solids. They are colourless,

neutral substance with characteristic sweet, alcoholic odour and burning taste.

(b) The lower alcohols are readily soluble in water and the solubility decreases with the increase in molecular

weight. The solubility of alcohols in water can be explained due to the formation of hydrogen bond between the highly polarized -OH groups present both in alcohols and water. However, in higher alcohols, the hydrocarbon character (alkyl chain) increases, showing a steric hindrance. Hence, the solubility in water decreases. When the ratio of C:OH is more than 4, alcohols have little solubility in water. (c) Boiling points of alcohols are much higher than those of the corresponding alkanes. It is due to the intermolecular hydrogen bonding present between the hydroxyl groups of the two molecules of an alcohol with the result several molecules are associated to form a large molecule. Among the isomeric alcohols, b.p. and m.p. show the following trend.

Primary > Secondary > Tertiary

This is because of the fact that in secondary and tertiary alcohols, the alkyl part (hydrogen character) outweighs

the -OH group due to branching. G Lower alcohols form solid addition compounds with anhydrous metallic salts like CaCl 2 and MgCl 2 , viz., CaCl 2 4C 2 H 5

OH and MgCl

2 .6C 2 H 5 OH

By analogy to water of crystallization, these alcohols molecules are referred to as alcohols of crystallization.

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