Revision Notes for Class 12 CBSE Chemistry, Alcohols, Phenols and Ethers - Topperlearning

8/10/2019 Revision Notes for Class 12 CBSE Chemistry, Alcohols, Phenols and Ethers - Topperlearning

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CHEMISTRY ALCOHOLS, PHENOLS AND ETHERS

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Alcohols Phenols and Ethers

TOP Concepts:

1. Structure of alcohols, phenols and ethers

2. Preparation of alcohols





3. Preparation of phenols

4. Physical properties of alcohols and phenolsa. Boiling points:

Boiling points of alcohols and phenols are higher in comparison to other classes ofcompounds, namely hydrocarbons, ethers, haloalkanes and haloarenes of comparablemolecular masses. This is because the – OH group in alcohols and phenols is involvedin intermolecular hydrogen bonding.

The boiling points of alcohols and phenols increase with increase in the number ofcarbon atoms. This is because of increase in van der Waals forces with increase in thesurface area.

In alcohols, the boiling points decrease with increase in branching in the carbon chain.This is because of decrease in van der Waals forces with decrease in the surface area.





b. Solubility Alcohols and phenols are soluble in water due to their ability to form hydrogen bonds

with water molecules.

The solubility of alcohols decreases with increase in the size of alkyl/aryl (hydrophobic)groups.

5. Chemical properties of alcoholsa. Reactions involving cleavage of O – H bond: Alcohols react as nucleophiles

b. Reactions involving cleavage of carbon –oxygen (C – O) bond inalcohols: Protonated alcohols react as electrophilesc. Dehydrationd. Oxidation

6. Reactions of alcohols and phenols involving cleavage of O – H bonda. Reaction with metals:

b. Esterification:





7. Reactions of alcohols involving cleavage of the carbon – oxygen (C – O) bond:

a. Reaction with hydrogen halides:

conc.HCl ZnCl 2Lucas reagent 2ROH + HX RX + H O

b. Reaction with phosphorus trihalides:

3ROH + PX 3 → 3R– X + H 3PO 3 (X = Cl, Br)

c. Dehydration:

c. Oxidation:

Cu,573Kor

CrO 3or

PCC

Cu,573Kor

CrO 3

Cu,573Kor

KMnO 4

Acidified potassium permanganate

Pr imary alcohol Aldehyde

Secondary alcohol Ketone

Tertiary alcohol Alkene

Alcohol Carboxylic acid





8. Chemical properties of phenols

9. Acidic naturea. Phenol > H

2O > Primary alcohol > Secondary alcohol > Tertiary alcohol

The acidic character of alcohols is due to the polar nature of the O – H bond.

The alkyl group is an electron-releasing group ( – CH 3, – C 2H5), or it has electron-releasing inductiveeffect (+I effect).Due to the +I effect of alkyl groups, the electron density on oxygen increases.This decreases the polarity of the O – H bond. Hence, the acid strength decreases.

b. Phenol is more acidic than alcohol because In phenol, the hydroxyl group is directly attached to the sp 2 hybridised carbon of the benzene

ring which acts as an electron-withdrawing group. Whereas in alcohols, the hydroxyl group isattached to the alkyl group which has an electron-releasing inductive effect.

In phenol, the hydroxyl group is directly attached to the sp 2 hybridised carbon of the benzenering. Whereas in alcohols, the hydroxyl group is attached to the sp 3 hybridised carbon of thealkyl group. The sp 2 hybridised carbon has higher electronegativity than the sp 3 hybridisedcarbon. Thus, the polarity of the O – H bond of phenols is higher than that of alcohols. Hence,the ionisation of phenols is higher than that of alcohols.

The ionisation of an alcohol and a phenol occurs as follows:





In alkoxide ion, the negative charge is localised on oxygen, while in phenoxide ion, the charge isdelocalised.

The delocalisation of the negative charge makes the phenoxide ion more stable and favours theionisation of phenol. Although there is charge delocalisation in phenol, its resonance structures havecharge separation due to which the phenol molecule is less stable than the phenoxide ion.

c. In substituted phenols, the presence of electron-withdrawing groups such as the nitro groupenhances the acidic strength of phenol. On the other hand, electron-releasing groups, such asalkyl groups, decrease the acidic strength.It is because electron-withdrawing groups lead to effective delocalisation of the negative charge inthe phenoxide ion.

10. How to distinguish between some important pair of organic compounds

a. Phenol and alcohol: Phenol on reaction with neutral FeCl 3 gives purple colour, whereas alcohols do not give purplecolour.

6C6H

5OH + Fe 3+ → [Fe(OC

6H

5)

6]3− + 6H +

Purple colour

b. Primary, secondary and tertiary alcohol: Lucas reagent test:

conc.HCl ZnCl 2Lucas reagent 2

ROH + HCl RCl + H O

If it is a primary alcohol, then no turbidity appears at room temperature. Turbidity appears only onheating.If it is a secondary alcohol, then turbidity appears in 5 minutes.If it is a tertiary alcohol, then turbidity appears immediately.





a. Methanol and ethanol:Iodoform test:Ethanol when reacted with I 2 and NaOH or NaOI gives a yellow ppt. of iodoform because of thepresence of the CH 3 –CH (OH) − group.

C 2H5OH + 4I 2+ 6NaOH CHI 3 + 5NaI + 5H 2O + HCOONa

Yellow ppt.CH 3OH + I 2+ NaOH No yellow ppt.

11. Preparation of ethers

12. Physical properties of ethers a. Miscibility:

Miscibility of ethers with water resembles those of alcohols of the same molecular mass. This isbecause similar to alcohols, oxygen of ether can also form hydrogen bonds with the watermolecule.

b. Boiling points:Ethers have much lower boiling points than alcohols. This is due to the presence of hydrogenbonding in alcohols. Hydrogen bonding is absent in ethers.





13. Chemical properties of ethersa. Cleavage of C – O bond in ethers:

R – O –R’ + HX → R–X + R’OH Excess

The order of reactivity of hydrogen halides is as follows:HI > HBr > HCl The alkyl halide formed is always the lower alkyl group. If a tertiary alkyl group is present, then the alkyl halide is always tertiary. In phenolic ethers, the cleavage occurs with the formation of phenol and alkyl halide.

b. Electrophilic substitution reaction in aromatic ethers:




14. Some important reactions for conversions

a. Conversion 1:

b. Conversion 2:

c. Alcohol from Grignard’s reagent :

H O H O2 2

R ' R '

RCHO R 'MgX RCH OMgX RCH OMgX Mg(OH)X

Revision Notes for Class 12 CBSE Chemistry, Alcohols, Phenols and Ethers - Topperlearning

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