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HYDROXY COMPOUNDS (ALCOHOLS) Click me for intro!
HYDROXY COMPOUNDS
(ALCOHOLS)
Click me
for intro!

1

INTRODUCTION  Alkane with hydroxyl group (–OH)  General formula for aliphatic alcohol, C n H
INTRODUCTION
 Alkane with hydroxyl group (–OH)
 General formula for aliphatic
alcohol, C n H 2n+1 OH
 Aromatic alcohol – phenol (-OH
attached to the benzene rings)

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INTRODUCTION CH 2 -OH OH CH 3 CH 2 -OH ALIPHATIC ALCOHOL (–OH group attached directly
INTRODUCTION
CH 2 -OH
OH
CH 3 CH 2 -OH
ALIPHATIC ALCOHOL (–OH group attached
directly to the alkyl group)
3
INTRODUCTION OH OH OH CH 3 Br AROMATIC ALCOHOL (–OH group attached directly to the aryl
INTRODUCTION
OH
OH
OH
CH 3
Br
AROMATIC ALCOHOL (–OH group attached
directly to the aryl group)
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CLASSIFICATION  Methyl alcohol CH 3 -OH  1 0 Alcohols R-CH 2 -OH R 
CLASSIFICATION
 Methyl alcohol
CH 3 -OH
 1 0
Alcohols
R-CH 2 -OH
R
 2 0 Alcohols
R-CH-OH
R
 3 0
Alcohols
R-C-OH
R
5
NOMENCLATURE Structure General name IUPAC name CH 3 CH 3 -OH CH 2 -OH methyl alcohol
NOMENCLATURE
Structure
General name
IUPAC name
CH 3
CH 3
-OH
CH 2 -OH
methyl alcohol
ethyl alcohol
methanol
ethanol
CH 3 CH(OH)CH 3
isopropyl alcohol
2-propanol
cyclohexyl
cyclohexanol
OH
alcohol
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Naming the alcohol 1.The suffix ‘–e’ in the alkane parent name is replaced by ‘–ol’ 2.The
Naming the alcohol
1.The suffix ‘–e’ in the alkane parent name
is replaced by ‘–ol’
2.The location of the –OH on the longest
chain is given by the smallest possible
number

7

IUPAC rules for naming alcohols 1.Determine parent name 2.Give the lowest number to the carbon bearing
IUPAC rules for naming
alcohols
1.Determine parent name
2.Give the lowest number to the carbon
bearing the –OH group
3.Identify substituent groups and their
position
4.Name the alcohol

8

Naming Alcohols, R-O-H: CH 3 CH 3 CHCH 2 CHCH 3 OH CH 3 CH 3
Naming Alcohols, R-O-H:
CH 3
CH 3 CHCH 2 CHCH 3
OH
CH 3
CH 3 CCH 2 CH 2 CH 3
OH
4-methyl-2-pentanol
2-methyl-2-pentanol
2 o
3 o
CH 3
HO-CHCH 2 CH 3
CH 3 CH 2 CH 2 -OH
sec-butyl alcohol
n-propyl alcohol
2-butanol
1-propanol
2 o
1 o
9
Naming Alcohols
Naming Alcohols

10

For phenol, C attach to the –OH group is C 1 OH OH OH CH 3
For phenol, C attach to the
–OH group is C 1
OH
OH
OH
CH 3
CH
CH 3
Br
2
3-ethylphenol
3-bromophenol
2-methylphenol
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Alcohol with 2 hydroxy groups Structure General name IUPAC name CH 2 (OH)CH 2 -OH ethylene
Alcohol with 2 hydroxy groups
Structure
General name
IUPAC name
CH 2 (OH)CH 2 -OH
ethylene glycol
1,2-ethanediol
CH 3 CH(OH)CH
-OH
2
1,2-propanediol
HO-CH 2
CH 2 CH
-OH
2
OH-CH 2
CHCH 2
-OH
propylene glycol
trimethylene
glycol
glycerol
1,3-propanediol
1,2,3-propanetriol
OH
12
Benzene derivatives with 2 –OH groups are name as benzenediol OH OH OH OH OH OH
Benzene derivatives with 2 –OH groups are
name as benzenediol
OH
OH
OH
OH
OH
OH
1,4-benzenediol
1,3-benzenediol
1,2-benzenediol
(hydroquinone)
(resorcinol)
(catechol)

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EXCERCISE 1. Name the following compounds using IUPAC nomenclature (a) -CH 2 CH(CH 3 )CH 2
EXCERCISE
1. Name the following compounds using IUPAC nomenclature
(a)
-CH 2 CH(CH 3 )CH 2 -OH
(b)
-OH
NO 2
(b)
-OH
Br

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PHYSICAL PROPERTIES  Most simple alcohols are liquids  MeOH & EtOH are volatile liquids, b.p.
PHYSICAL PROPERTIES
 Most simple alcohols are liquids
 MeOH & EtOH are volatile liquids, b.p.
65 o C & 78 o C respectively
 M r
,
b.p.
 ROH with C > 12 are solids
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PHYSICAL PROPERTIES  No. of –OH , b.p.  b.p. ROH > alkane & RX because
PHYSICAL PROPERTIES
 No. of –OH
, b.p.
 b.p. ROH > alkane & RX because
of H-bonding
 b.p. ROH straight chain > ROH
branch
 b.p. 1 o ROH > 2 o ROH > 3 o ROH

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PHYSICAL PROPERTIES (ii) Boiling point  As molecular weight increase, van der Waals forces increase, boiling
PHYSICAL PROPERTIES
(ii)
Boiling point
 As molecular weight increase, van der Waals
forces increase, boiling point will increase too.
For isomeric alcohol (same molecular
formula)
 increase in boiling point with increasing carbon
number.
 decrease in boiling point with branching.
 boiling point in descending order:-
1° alcohol  2° alcohol
 3° alcohol
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PHYSICAL PROPERTIES (Solubility) Alcohols and water have the ability to form inter-molecular H-bonding Methanol, ethanol &
PHYSICAL PROPERTIES
(Solubility)
Alcohols and water have the ability to form
inter-molecular H-bonding
Methanol, ethanol & propanol are completely
soluble in water
Solubility decreases with relative M r because of
the bigger hydrophobic area
Solubility increases with the no. of -OH groups

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PHYSICAL PROPERTIES (Solubility) Alcohols and water have the ability to form inter-molecular H-bonding Methanol, ethanol &
PHYSICAL PROPERTIES (Solubility) δ+ H δ- R O Hydrophilic area H Hydrogen δ- δ+ H O
PHYSICAL PROPERTIES
(Solubility)
δ+
H
δ-
R
O
Hydrophilic area
H
Hydrogen
δ-
δ+
H
O
bonding
R
OH
H
δ-
δ+
R
O
Hydrophobic area
H
δ+
H
O
δ-

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PHYSICAL PROPERTIES (Solubility) Phenol is not completely soluble in water below 66 o C, but completely
PHYSICAL PROPERTIES
(Solubility)
Phenol is not completely soluble in water below
66 o C, but completely soluble above this temp.
Phenol is a colourless crystalline solid which is
hygroscopic
4-nitrophenol is more soluble in water than 2-
nitrophenol because can form H-bonding with
water molecules

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PHYSICAL PROPERTIES (Solubility) 2-nitrophenol 4-nitrophenol δ- O δ- O δ+ O H H δ+ δ- δ+
PHYSICAL PROPERTIES
(Solubility)
2-nitrophenol
4-nitrophenol
δ-
O
δ-
O
δ+
O
H
H
δ+
δ-
δ+
H
N
O
δ-
O
N
δ+
O
O
δ+
δ-
δ-
H
O
Intramolecular H-bonding
δ+
H
H
Intermolecular H-bonding

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Acidity of phenol & alcohol phenol > water > alcohol  Ethanol, very weak acid &
Acidity of phenol & alcohol
phenol > water > alcohol
 Ethanol, very weak acid & only can react
with strong base such as Na or K to
produce a conjugate base (ethoxide ion)
CH 3 CH 2 -OH
CH 3 CH 2 -O - + H +

22

Acidity of phenol & alcohol  CH 3 CH 2 O - is e - richer
Acidity of phenol & alcohol
 CH 3 CH 2 O - is e - richer than OH - , thus H 2 O
> acidic than CH 3 CH 2 OH
 Phenol > acidic than H 2 O & CH 3 CH 2 OH
because phenoxide ion formed is more
stable
 The phenoxide ion formed is stabilised
by resonance effect

23

Acidity of phenol & alcohol - O H O release proton + H + Phenoxide ion
Acidity of phenol & alcohol
-
O
H
O
release proton
+ H +
Phenoxide ion
24
Phenoxide ion stability O - O O O - - - O δ- δ- δ- δ-
Phenoxide ion stability
O -
O
O
O
-
-
-
O δ-
δ-
δ-
δ-
25
Example: OH CH 2 CH 2 -OH CH 2 -OH OH acidity increase 26
Example:
OH
CH 2 CH 2 -OH
CH 2 -OH
OH
acidity increase
26
Example: COOH OH > > CH 3 CH 2 -OH ACIDITY DECREASE Na 2 CO 3
Example:
COOH
OH
>
>
CH 3 CH 2 -OH
ACIDITY
DECREASE
Na 2 CO 3
NaHCO 3
Weak bases
KOH
K, Na
NaOH
Strong bases
NaH
Very strong bases
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EXCERCISE 1. Arrange the following compounds in the order of increasing boiling point. Explain your answer.
EXCERCISE
1. Arrange the following compounds in the order of increasing
boiling point. Explain your answer.
1,2-ethanediol , n-butane , 1-propanol , 1,3-propanediol
2. Predict which of the compound is more soluble in water.
Briefly explain your answer.
(a) propane & 1-propanol
(b) 1-propanol & 1,2-propanediol
(c) 2-propanol & 2-pentanol

28

PREPARATION OF ALCOHOLS 1. Fermentation of carbohydrate -fermentation of sugars by yeast to form ethanol 2CH
PREPARATION OF
ALCOHOLS
1.
Fermentation of carbohydrate
-fermentation of sugars by yeast to
form ethanol
2CH 3 CH 2 OH + 2CO 2
C 6 H 12 O 6

29

PREPARATION OF ALCOHOLS 2. Hydration of Alkenes follows Markovnikov’s rule Example:- H 2 O / H
PREPARATION OF
ALCOHOLS
2. Hydration of Alkenes
follows Markovnikov’s rule
Example:-
H 2 O / H 2 SO 4
CH 3 CH=CH 2
CH 3 CH-CH 3
OH

30

PREPARATION OF ALCOHOLS Mechanism CH 3 CH=CH 2 + H + CH 3 CH-CH 3 2
PREPARATION OF
ALCOHOLS
Mechanism
CH 3 CH=CH 2 + H +
CH 3 CH-CH 3
2 o carbonium
+
●●
OH -
CH 3 CH-CH 3
OH
●●
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PREPARATION OF ALCOHOLS 3. Hydrolysis of Haloalkanes RX + OH - (aq) ROH + X -
PREPARATION OF
ALCOHOLS
3.
Hydrolysis of Haloalkanes
RX + OH - (aq)
ROH + X -
CH 2 Cl
CH 2 OH
+ NaOH (aq)
32
PREPARATION OF ALCOHOLS 4. Addition of Grignard reagent to carbonyl compounds 1 0 , 2 0
PREPARATION OF
ALCOHOLS
4. Addition of Grignard reagent to
carbonyl compounds
1 0 , 2 0 & 3 0 alcohols can be prepared by
addition of Grignard reagent with carbonyl
compounds followed by hydrolysis

33

PREPARATION OF ALCOHOLS (a) Formation of 1 o alcohols (Grignard reagent + methanal) CH 3 CH
PREPARATION OF
ALCOHOLS
(a) Formation of 1 o alcohols (Grignard reagent + methanal)
CH 3 CH 2 -MgCl + H 2 C=O
CH 3 CH 2 CH 2 -
OMgCl
methana
l
H 3 O +
1
o
Alcohol
CH 3 CH 2 CH 2 -OH
+ Mg(OH)Cl
34
PREPARATION OF ALCOHOLS (b) Formation of 2 o alcohols (Grignard reagent + aldehyde) CH 3 CH
PREPARATION OF
ALCOHOLS
(b) Formation of 2 o alcohols (Grignard reagent + aldehyde)
CH 3
CH 3 CH 2 -MgCl + HC=O
CH 3
CH 3 CH 2 CH-
ethan
OMgCl
al
H 3 O +
2 o Alcohol
CH 3
CH 3 CH 2 CH-OH
+ Mg(OH)Cl

35

PREPARATION OF ALCOHOLS (c) Formation of 3 o alcohol (Grignard reagent + ketone) O O-MgCl CH
PREPARATION OF
ALCOHOLS
(c) Formation of 3 o alcohol (Grignard reagent + ketone)
O
O-MgCl
CH 3 -MgCl + CH 3 -C-CH 3
CH 3 -C-CH 3
propanon
CH 3
e
H 3 O +
O-H
3
o
CH 3 -C-CH 3 +
Alcohol
Mg(OH)Cl CH
3
36
EXCERCISE 1. Write the chemical equation for the following reaction: i. ii. tert-butyl alcohol from an
EXCERCISE
1. Write the chemical equation for the following reaction:
i.
ii.
tert-butyl alcohol from an alkene
isopropyl alcohol from an alkyl halide
2. Draw the structure of A, B and C:
i.
CH 3
CH 3 -C-MgCl +
CH 3
O
-C-H
A
ii.
H 2 O / H +
-CH=CH-CH 3
B
+
C
37
REACTIONS OF ALCOHOL (a) As an acid In an aqueous solution alcohol reacts as a very
REACTIONS OF ALCOHOL
(a) As an acid
In an aqueous solution alcohol reacts as a very weak acid
ROH +
H 2 O
RO - + H 3 O +
Reacts with Na or NaH & form a very strong base
alkoxide ion
CH 3 CH 2 OH + Na
CH 3 CH 2 O - Na + + 1/2H 2
38
REACTIONS OF ALCOHOL (a) As a base With the presence of lone pair of e -
REACTIONS OF ALCOHOL
(a) As a base
With the presence of lone pair of e - at the O atom,
alcohol can accept proton from an acid
●●
●●
CH 3 CH 2 -O-H + HA
CH 3 CH 2 O + -H + A -
●●
H
39
REACTIONS OF ALCOHOL (1) Esterification Alcohol reacts with carboxylic acid under reflux & is catalysed by
REACTIONS OF ALCOHOL
(1) Esterification
Alcohol reacts with carboxylic acid under reflux &
is catalysed by mineral acids (H 2 SO 4 or HCl) to
form ester.
General reaction:-
O
O
H + ,
R-C-OH + R’-OH
R-C-OR’ + H-O-H
acid
alcohol
ester
water
40
REACTIONS OF ALCOHOL (1) Esterification Example:- O O H + , CH 3 C-OH + CH
REACTIONS OF ALCOHOL
(1) Esterification
Example:-
O
O
H + ,
CH 3 C-OH + CH 3 -OH
CH 3 C-OCH 3 + H-O-H
ethanoic acid
methanol
methyl ethanoate
41
REACTIONS OF ALCOHOL (1) Esterification Alcohol reacts with acyl chloride to form ester O O base
REACTIONS OF ALCOHOL
(1) Esterification
Alcohol reacts with acyl chloride to form ester
O
O
base
CH 3 C-Cl +
CH 3 -OH
CH 3 C-OCH 3 + HCl
ethanoil chloride
methanol
methyl ethanoate
42
REACTIONS OF ALCOHOL (2) Dehydration of alcohol •Involve formation of carbocation •Possible of rearrangement H 2
REACTIONS OF ALCOHOL
(2) Dehydration of alcohol
•Involve formation of carbocation
•Possible of rearrangement
H 2 SO 4
(con.)
CH 3 CH 2 CH 2 OH
CH 3 CH=CH 2
180
0
propanol
C
propene
43
REACTIONS OF ALCOHOL (3) Formation of haloalkane •ROH reacts with HX to form RX •The reaction
REACTIONS OF ALCOHOL
(3) Formation of haloalkane
•ROH reacts with HX to form RX
•The reaction rates are in the order
HI > HBr > HCl (HF non-reactive)
•Reactivity of alcohols
3 o ROH > 2 o ROH > 1 o ROH > phenol

44

REACTIONS OF ALCOHOL General Reaction ROH + HX RX + H 2 O Example:- CH 3
REACTIONS OF ALCOHOL
General Reaction
ROH + HX
RX + H 2 O
Example:-
CH 3 CH 2 CH 2 OH + HBr
CH 3 CH 2 CH 2 Br + H 2 O

45

REACTIONS OF ALCOHOL (3) Formation of haloalkane •ROH reacts with PX 3 , PX 5 ,
REACTIONS OF ALCOHOL
(3) Formation of haloalkane
•ROH reacts with PX 3 , PX 5 , SOCl 2
General reaction:
(i)3ROH + PX 3
(ii)ROH + PCl 5
(iii)ROH + SOCl 2
3RX + H 3 PO 3
RCl + POCl 3 + HCl
RCl + SO 2 + HCl

46

REACTIONS OF ALCOHOL (4) Oxidation of alcohols • Common oxidising agents are potassium permanganate (VII), (KMnO
REACTIONS OF ALCOHOL
(4) Oxidation of alcohols
• Common oxidising agents are potassium
permanganate (VII), (KMnO 4 /H + ) and
potassium dichromate (K 2 Cr 2 O 7 /H + )
• Oxidation product depends on the class of
alcohol used

47

REACTIONS OF ALCOHOL (4) Oxidation of 1 o alcohol • 1 o R-OH can be oxidised
REACTIONS OF ALCOHOL
(4) Oxidation of 1 o alcohol
• 1 o R-OH can be oxidised to give an aldehyde.
Further oxidation would give a carboxylic acid
O
O
[O]
[O]
RCH 2 OH
RC-H
RC-OH
1 o alcohol
aldehyde
carboxylic acid
48
REACTIONS OF ALCOHOL (4) Oxidation of 1 o alcohol Example:- K 2 Cr 2 O 7
REACTIONS OF ALCOHOL
(4) Oxidation of 1 o alcohol
Example:-
K 2 Cr 2 O 7 /H +
CH 3 CH 2 OH
O
CH 3 C-H
K 2 Cr 2 O 7 /H +
O
CH 3 C-OH + Cr 3+
green
orange
49
REACTIONS OF ALCOHOL (4) Oxidation of 1 o alcohol • Sarett-Collins reagent is a special oxidation
REACTIONS OF ALCOHOL
(4) Oxidation of 1 o alcohol
• Sarett-Collins reagent is a special oxidation
agent to change a 1 o alcohol to an aldehyde
• CrO 3 is added to excess pyridine to form
pyridinium chlorochromate (PCC)
CH 3 CH 2 CH 2 OH + PCC
O
CH 3 CH 2 C-H
propanol
propanal
50
REACTIONS OF ALCOHOL (4) Oxidation of 2 o alcohol • form ketone which cannot be oxidised
REACTIONS OF ALCOHOL
(4) Oxidation of 2 o alcohol
• form ketone which cannot be oxidised
further under normal conditions
R
[O]
R’CH-OH
R
R’C=O + H 2 O
2 o alcohol
ketone
CH 3
CH 3 CH-OH
KMnO 4 /H +
CH 3
CH 3 C=O + H 2 O
2-propanol
propanone
51
REACTIONS OF ALCOHOL (4) Oxidation of 3 o alcohol • Does not undergo oxidation under normal
REACTIONS OF ALCOHOL
(4) Oxidation of 3 o alcohol
• Does not undergo oxidation under normal
condition
R
[O]
R’-C-OH
no reaction
R’’
3 o alcohol

52

Chemical test for R-OH  Lucas test • Lucas reagent : HCl (con.) + ZnCl 2
Chemical test for R-OH
 Lucas test
• Lucas reagent : HCl (con.) + ZnCl 2
• 3 o R-OH + Lucas reagent – reacts
immediately to form cloudy haloalkane
• 2 o R-OH + Lucas reagent –takes about 5-10
minutes to form cloudy
• 1 o R-OH + Lucas reagent – no visible
changes unless heated

53

Example: OBSERVATIONS : 1 o CH 2 OH HCl / ZnCl 2 Does not turn cloudy
Example:
OBSERVATIONS :
1
o
CH 2 OH
HCl / ZnCl 2
Does not turn
cloudy
OH
2
o
HCl / ZnCl 2
Turn cloudy
within 5 minute

54

OBSERVATIONS : CH 3 3 o OH HCl / ZnCl 2 Turn cloudy immediately 55
OBSERVATIONS :
CH 3
3
o
OH
HCl / ZnCl 2
Turn cloudy
immediately
55
Haloform Reaction  Methyl carbinol cleavage to give Carboxylic acids and Haloform H CH 3 C
Haloform Reaction
 Methyl carbinol cleavage to give Carboxylic
acids and Haloform
H
CH 3
C
H
X 2 , H +
OH -
HCX
H
C
OH
3 +
OH
O
H
X 2
CH 3
C
R
, H +
OH -
HCX 3 + R
C
OH
OH
O
56
IODOFORM TEST OH CH 3 CH 2 CCH 3 + 3I 2 base (OH - )
IODOFORM TEST
OH
CH 3 CH 2 CCH 3 +
3I 2
base (OH - )
2-butanol
CH 3 CH 2 COO - + CHI 3 ↓
yellow precipitate
(iodoform)
57
PHENOL Manufacture of phenol by Cumene process (a) Friedel-Crafts reaction CH 3 -CH-CH 3 AlCl 3
PHENOL
Manufacture of phenol by Cumene process
(a) Friedel-Crafts reaction
CH 3 -CH-CH 3
AlCl 3
+ CH 3 CH=CH 2
Isopropylbenzene
Isopropylbenzene
(cumene)
(cumene)
58
PHENOL (b) Oxidation of Cumene CH 3 -CH-CH 3 O -OH CH 3 -C-CH 3 120
PHENOL
(b) Oxidation of Cumene
CH 3 -CH-CH 3
O -OH
CH 3 -C-CH 3
120
0 C
+ O 2
Cumene
hydroperoxide
(c) Decomposition & rearrangement
CH 3
-C-O-OH
CH 3
H 2 SO 4
O
-OH + CH 3 CCH 3
59
Reactions of Phenol 1. Reaction at functional group -OH (a) Reaction with Na OH O -
Reactions of Phenol
1. Reaction at functional group -OH
(a) Reaction with Na
OH
O - Na +
+ Na
+ ½ H 2
60
Reactions of Phenol 1. Reaction at functional group -OH (b) Reaction with NaOH OH O -
Reactions of Phenol
1. Reaction at functional group -OH
(b) Reaction with NaOH
OH
O - Na +
+ NaOH
+ H 2 O
CH 3 CH 2 OH + NaOH
no reaction
61
Reactions of Phenol 2. Electrophilic substitution reactions (a) Halogenation (Bromination) -OH is ortho-para director in Br
Reactions of Phenol
2. Electrophilic substitution reactions
(a) Halogenation (Bromination)
-OH is ortho-para director
in Br 2 , aqueous solution, white precipitate 2,4,6-
tribromophenol will form
OH
OH
Br
Br
+ 3Br 2 / H 2 O
+ 3HBr
Br
62
Reactions of Phenol 2. Electrophilic substitution reactions (a) Bromination to get monobromination (catalyst: FeBr 3 or
Reactions of Phenol
2. Electrophilic substitution reactions
(a) Bromination to get monobromination (catalyst:
FeBr 3 or CS 2 )
OH
OH
OH
Br
CS 2
+ Br 2
+
+ HBr
5
0 C
Br
63
Reactions of Phenol 2. Electrophilic substitution reactions OH OH (b) Nitration NO 2 Dilute HNO 3
Reactions of Phenol
2. Electrophilic substitution reactions
OH
OH
(b) Nitration
NO 2
Dilute HNO 3
+
Room temp.
OH
NO 2
OH
O 2 N
NO 2
Concentrated HNO 3
Yellow
precipitate
NO 2
64
Reactions of Phenol 3. Esterification phenol is a weaker nucleophile than alcohol since the lone pair
Reactions of Phenol
3. Esterification
phenol is a weaker nucleophile than alcohol
since the lone pair e - of O atom are delocalised
to the benzene ring
reacts with an acid derivative such as acid
chloride to form an ester
CH 3
OH
O-C=O
Cl
+ CH 3 -C=O
+ Cl -
65
Reactions of Phenol 4. Identification test for phenols phenol reacts with aqueous solution of iron (III)
Reactions of Phenol
4. Identification test for phenols
phenol reacts with aqueous solution of iron (III)
chloride giving a light purple complex
OH
OH
+ FeCl 3 (aq)
FeCl 3
Purple
complex
66
EXERCISE 1 Suggest a chemical test to differentiate the following pairs of compounds. State the reagents,
EXERCISE 1
Suggest a chemical test to differentiate the following pairs of
compounds. State the reagents, observations and write
chemical equations involved.
(a)
methanol from ethanol
(b)
2-methyl-1-propanol from 2-methyl-2-propanol
(c)
cyclohexanol from cyclohexane
(d)
phenol from benzyl alcohol
(e)
o-methylphenol from 2-methylcyclohexanol

67

EXERCISE 2 Compound A (C 4 H 10 O) undergoes oxidation to form compound B (C
EXERCISE 2
Compound A (C 4 H 10 O) undergoes oxidation to form compound
B (C 4 H 8 O). Oxidation of B gives compound C (C 4 H 8 O 2 ).
Reaction of A with hot concentrated sulphuric acid yields
compound D (C 4 H 8 ). Hydration of D gives compound E
(C 4 H 10 O) which cannot be oxidised. A and E are isomeric.
Suggest the structure of A, B, C, D and E. Rasionalise your
answer.

68

Common Used Of Alcohol And Phenol  Ethyl alcohol is a poison. LD50 = ~10g/Kg orally
Common Used Of Alcohol
And Phenol
 Ethyl alcohol is a poison.
LD50 =
~10g/Kg orally in mice.- Nausea,
vomiting, flushing, mental excitement or
depression, drowsiness, impaired
perception, loss of coordination, stupor,
coma, death may occur.
(intoxication)
 Phenol is an important industrial
chemical. Major use is in phenolic resins
for adhesives and plastics.

69

Phenols in Medicine  Many phenols are used as antiseptics and disinfectants. OH OH OH OH
Phenols in Medicine
 Many phenols are used as antiseptics and
disinfectants.
OH
OH
OH
OH
OH
CH 2 CH 2 CH 2 CH 2 CH 2 CH 3
Phenol
Resorcinol
4-Hexylresorcinal
(antiseptic)
(antiseptic)
70
Derivatives of Phenol  Compounds of phenol are the active ingredients in the essential oils of
Derivatives of Phenol
 Compounds of phenol are the active ingredients in the
essential oils of cloves, vanilla, nutmeg, and mint.
71