Organic Chemistry

Chapter 5 Alcohol

Candidates should be able to:

1. Write the general formula for hydroxyl compounds; 2. Name hydroxyl compounds according to the IUPAC nomenclature; 3. Classify alcohols into primary, secondary and tertiary alcohol; 4. State the physical properties of hydroxyl compounds. 5. Classify the reactions of alcohols i) ROH bond is broken: the formation of an alkoxide with sodium, esterification, acylation, oxidation to carbonyl compounds and carboxylic acids; ii) ROH is broken and OH is replaced by other groups: the formation of haloalkanes and the dehydration to alkenes and ethers;

1. Introduction
i. General formula CnH2n+1OH ii. Functional group hydroxyl iii. Divided into 2 group- i) aliphatic ii) aromatic

2. IUPAC nomenclature i. Aliphatic alcohol compound are named by replacinge of corresponding alkane by suffix ol. ii. The longest carbon chain iii. Number the carbon atom with OH group with the lowest number possible iv. If there are 2 hydroxyl groups diol, 3 hydroxyl groups - triol
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Nomenclature of cyclic Alcohols:

1. When an OH group is bonded to a ring, the ring is numbered beginning with the OH group. 2. Because the functional group is at C1, the 1 is usually omitted from the name. 3. The ring is then numbered in a clockwise or counterclockwise fashion to give the next substituent the lowest number.
Examples: Naming cyclic alcohols

Activity 1
Name the compounds according to the IUPAC nomenclature :a. CH3OH b. CH3CH2OH c. CH3CHOHCH3 d. COHCH3CH3CH3 e. CH2OHCH2OH f. CH2OHCHOHCH2OH
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3. Classification
Alcohols contain a hydroxy group (OH) bonded to an sp3 hybridized carbon and may be 1o, 2o or 3o.

4. Physical Properties:
1. Boiling point of alcohols is higher than corresponding RMM. ????

Stearic factors affect hydrogen bonding.

ii. Lower members of alcohol, the higher solubility of that alcohol

Solubility decreases

5. Reaction of alcohol

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a) bond fusion between O and H ( RO-H)

i) formation of an alkoxide with sodium General eq: RO-H + Na Example : C2H5OH + Na RONa + H2

C2H5ONa + H2

Observation : .

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ii) Esterification General eq :

1

Condition :.. Observation :..

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iii) Oxidation

Reagent: Condition :. Observation :.

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Example

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Activity 2 - worksheet

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b) Fusion of R-OH bond

i) Dehydration Reagent excess H2SO4/ 170C

CH3CH2OH R-OH

R=R

ROR

CH2=CH2
ALKENES

CH3CH2-O-CH2CH3
ETHER

ii) Halogenations
R-OH HX ZnCl2, heated R-X

iii) With PCl3 /PCl5/ SOCl2 R-OH PCl3 /PCl5/ SOCl2

r.t

R-X + HCl

iv) Combustion - CO2 + H2O

Activity 3- worksheet

Take a break

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Lucas test / Lucas reagent R-OH HX R-X ZnCl2, heated Observation : 1-cloudy after more than 5 min 2-cloudy about 5 min H CH3 C R OH

3- immediately

Iodoform Test identify the presence of alcohol and carbonyl CH C=O

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R @H Reagent aqueous iodine and aqueous NaOH Observation yellow crystals