Organic chemistry

Alcohols （ R-OH ）
and Carboxylic acids （ R-C-OH ）

=
O
alkyl

an alkyl substituent is an alkane missing one hydrogen

CnH2n+2 - H = CnH2n+1 -

R-
Review
Alkane Alkene Alkyl
-ane -ene -yl
1 meth- methane methene methyl
2 eth- ethane ethene ethyl
3 prop- propane propene propyl
4 but- butane butene butyl
5 pent- pentane pentene pentyl
6 hex- hexane hexane hexyl
-OH and -COOH Functional
groups

O
R O H R C
O H

alkyl + hydroxyl alkyl + carboxyl

alcohol carboxylic acid

 Alkyl Alcohol Carboxylic acid

-yl -ol -oic acid

1 meth- methyl methanol methanoic acid
2 eth- ethyl ethanol ethanoic acid
3 prop- propyl propanol propanoic acid
4 but- butyl butanol butanoic acid
5 pent- pentyl pentanol pentanoic acid
6 hex- hexyl hexanol hexanoic acid
Alcohol

H
O C H
H H

methanol

CH3OH
 H H
O C C H
H H H

ethanol

CH3CH2OH
General formula : CnH2n+1OH or R-OH

Functional group : hydroxyl (-OH)

4 3 2 1
Naming : CH3CH2CH2CH2OH Butan-1-ol
4 3 2 1
CH3CH2CHCH3
OH Butan-2-ol
 naming
CH3

CH3 CH2 CH CH CH3 2,3-dimethyl-pentane

CH3

CH3 CH2 C CH2 2-methyl-1-butene

CH3
Physical property

※ High boiling point （ compared with

alkanes ）
※ Neutral, colorless, volatile liquid
※ not conduct electricity
※ Molecules are Polar （ be like water ）
※ Use as solvent （ for paint, glues…… ）

H - OH
miscible
CH3CH2 - OH
How do we get ethanol?

1. Fermentation (anaerobic respiration)

Yeast
C6H12O6(aq) → 2C2H5OH(l) + 2CO2(g)

aerobic respiration ？

2. Hydration of ethene

CH2 CH2 + H2 O CH3 CH2

OH
Chemical property

1. Combustion

C2H5OH(l) + 3O2(g) → 2CO2(g) + 3H2O(g)

H H
O C C H CH3CH2OH CH3CH2-OH OH
H H H
 P235
Question 1

2. Oxidation

H H H O
H C C O H + 2[O] H C C + H2O
H H H O H
potassium dichromate(VI)
K2Cr2O7 Carboxylic acid
or group
potassium manganate(VII)
KMnO4
3. Esterification
H O
H C C ＋ H H

H O H H O C C H
H H
H O
conc H C C H H
H2SO4 + HO-H
H O C C H
Ester H H
ester
General formula : CnH2n+1COOCxH2x+1
O

=
Functional group : ester group (-C-O-)

Physical property: 1. strong and pleasant smells

2. immiscible with water
3. used in flavourings and perfumes
4. Fat (animal) and oil (plant) are ester
 formula name

acid part + alcohol part alcohol part + acid part

H O
H C C H H
ethyl ethanoate
H O C C H
H H
O
H C H H H
propyl methanoate
O C C C H
H H H
Carboxylic acids

O
O C H
H

methanoic acid

HCOOH
 O H
O C C H
H H

ethanoic acid

CH3COOH
General formula : CnH2n+1COOH or R-COOH

Functional group : carboxyl （ -COOH ）

4 3 2 1
Naming : CH3CH2CH2COOH Butanoic acid

5 4 3 2 1
CH3CH2CH2CH2COOH Pentanoic acid
Physical property

※ b.p and m.p increase with number of carbons

※ acidic liquid
※ conduct electricity
※ miscible with water
Chemical property

1. react with base

CH3COOH(aq) + NaOH(aq) → CH3COONa(aq) + H2O(l)
sodium ethanoate
2. react with metal

3. react with carbonate

4. indicators
5. react with alcohol
 Other carboxylic acids

Painkiller
aspirin Fever
Inflammation

Ascorbic acid
Production of collagen
(vitamin C )
 Other carboxylic acids

Citric acid citrus 柑橘类

Soaps

Saponification Fat
+ NaOH → soap
： Oil
O-
O
—

hydrophobic hydrophilic
 Soapless detergents
do not form scum
with hard water

SO3- Na+

Benzene + dodecene → dodecylbenzene + sulfuric acid

→ dodecylbenzene sulfonic acid + NaOH

→ Sodium 3-dodecylbenzene sulfate