CHEMISTRY(XII) CHAPTER 11 (Alcohols, Phenols and Ethers)

Short Questions:
1. How will you distinguish between primary secondary and tertiary alcohols by Lucas test?
Primary, secondary and tertiary alcohols are identified and distinguished by reacting them with concentrated
HCl in anhydrous ZnCl2. An oily layer of alkyl halides separates out in these reactions as follows;
(i) Tertiary alcohols form an oily layer immediately.
R3C-OH + HCl R3C-Cl + H2O
(ii) Secondary alcohols for an oily layer in 5 to 10 minutes primary.
R2CHOH + HCl R3CH-Cl + H2O
(iii) Primary alcohols form an oily layer only on heating.

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R-CH2 OH + HCl R-CH2-Cl + H2O
2. Picric acid is a phenol which behaves like an acid. Justify.
Picric acid 2,4,6 trinitrophenol has 3 nitro groups present which have electron withdrawing nature. Nitro

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groups can engage the negative charge on benzene ring in delocalization, setting the proton free for longer
time. So picric acid act as acid.
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3. Why ethers are referred to as inert compounds.
Ethers are comparatively inert substances. The reagents like ammonia, alkalies, dilute acids and metallic
sodium, have no reaction on ethers in cold state. Moreover, they are not oxidized or reduced easily. That’s
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why ethers are considered as inert.

4. Compare the reaction of conc.H2SO4 with
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(i) Ethyl alcohol

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Ethyl Alcohol gives different products with conc H2SO4 on different temperatures;
At 180C with conc. H2SO4.
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C2H5-OH CH2 = CH2 + H20

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At 140C with conc. H2SO4.

2C2H5-OH C2H5-O-C2H5 + H20
(ii) Phenol.
Phenol reacts with conc sulfuric acid at room temp. as follows;

2 + 2H2S04

o-hydroxybenzene p-hydroxybenzene
sulphonic acid sulphonic acid
5. Give preparation of methanol by the reaction between CO and H 2 (i.e. water gas).
On industrial scale methanol is prepared from a mixture of carbon monoxide and hydrogen. The gaseous
mixture is subjected to 200 atmospheres and then passed over heated catalyst mixture of ZnO and
Cr2O3 kept at 400O C to 450O C. This reaction results the formation of methanol vapors which are then
condensed to liquid state.

CO + 2H2 CH3-OH

6. Distinguish ethanol and tertiary butyl alcohol by Lucas Test.

Ethanol and tertiary butyl alcohol are distinguished by reacting them with concentrated HCl in anhydrous
ZnCl2. An oily layer of alkyl halides separates out in these reactions
1 Ethyl alcohol form an oily layer immediately
CH3-CH2 -OH + HCl CH3-CH2-Cl+H2O
2. Tertiary Butyl alcohol form an oily layer only on heating

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(C4H9)3C-OH + HCl (C4H9)3C -Cl + H2O
7. Prepare Phenol from Chlorobenzene by Dow’s method.
In this method chlorobenzene is treated with 10% NaOH at 360°C and 150 atmospheres pressure sodium

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phenoxide is produced which is treating with HCl gives phenol.
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8. How Will you convert:

i. Methanol into Ethanol
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𝐻𝐼
CH3OH → CH3I
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Ether
CH3I + Mg → CH3MgI
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𝐻3𝑂 +
CH3MgI + HCHO → CH3CH2OH
ii. Ethanol into Methanol
170−180𝐶
CH3CH2OH+ H2SO4 (conc.) → CH2=CH2
𝑂𝑧𝑜𝑛𝑜𝑙𝑦𝑠𝑖𝑠
CH2=CH2 +Zn/H20 → 2HCHO
𝐿𝑖𝐴𝑙𝐻
HCH0 → CH3OH
9. Write structural formulas of:
i. Methoxy ethane CH3-O-CH3
ii. Ethoxy benzene C6H5-O-C2H5
10. What are alcohols? How are they classified?
Alcohols are represented by a general formula ROH where R is an alkyl group.
On the bases of hydroxyl group, alcohols are classified into monohydric and polyhydric alcohols. Monohydric
alcohols contain one -OH group while polyhydric alcohol as may contain two, three or more OH groups and
and named as dihydric or trihydric alcohol, etc.
Monohydric alcohols are further classified into primary secondary and tertiary alcohols.
Primar Alcohol R-CH2-OH
Secondary Alcohol R2CH-OH
Tertiary Alcohol R3C-OH
11. Why absolute alcohol can’t be prepared by fermentation?
Alcohol obtained by fermentation is only up to 12% and never exceeds 14% because beyond this limit
enzymes become inactive. That’s why absolute alcohol cannot be prepared by fermentation.
12. What are primary and secondary alcohols? Give one example of each.

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Primar Alcohols are in which alpha carbon is further attached with only one carbon atom.
Ethanol CH3-CH2-OH
Secondary Alcohols are in which alpha carbon is further attached with two carbon atoms.

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Isopropyl Alcohol (CH3)2CH-OH
Tertiary Alcohols are in which alpha carbon is further attached with three carbon atoms.
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2-Methyl-2-Propanol (CH3)3C-OH
13. Give any four uses of Methyl alcohol.
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1. Methanol is widely used in the production of acetic acid and formaldehyde

2. In order to discourage the recreational consumption of ethanol, methanol is often added to it as a
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denaturant
3. This compound is also used as an antifreeze (an additive that is used to lower the freezing point of a
liquid) in many pipelines
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4. It is also used as solvent for fats, oils and paints.

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14. Write two uses of each of methanol and ethanol.

Uses of Methanol;
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i. Methanol is used as an antifreeze

ii. It is also used as solvent for fats, oils and paints
Uses of Ethanol;
i. It is used as a fuel in some countries
ii. It is used as preservative for biological specimens
15. How does phenol react with alkali?
Phenol reacts with sodium hydroxide solution to give a colorless solution containing sodium phenoxide.
16. How is Methylated spirit prepared?
Sometimes ethanol is denatured by addition of 10% methanol to avoid its use for drinking purpose. Such
alcohol is called methylated spirit. A small quantity of pyridine or acetone may also be added for this
purpose.
17. Why Phenol is acidic in nature?
Phenol is much more acidic than alcohols but less acidic than carboxylic acids. The reason why phenol is
acidic lies in the nature of the phenoxide ion. The negative
charge on oxygen atom can become involved with the ∏- electron cloud on the benzene ring. The negative
charge is thus delocalized in the ring and the phenoxide ion becomes relatively stable. This type of
delocalization is not possible with alcohols.

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18. Write structural formulas of:
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i. Carbolic acid
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ii. Glycerol
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19. Convert acetone into ethyl alcohol.

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Reduction 170−180𝐶 𝑂𝑧𝑜𝑛𝑜𝑙𝑦𝑠𝑖𝑠

CH3COCH3 → CH3CHOHCH3 + H2SO4 → CH3CH=CH2 → CH3CH2CHO + HCHO
Reduction
CH3CH2CHO → CH3CH2OH
20. Water has higher boiling point than Ethanol. Explain.
There is less extensive hydrogen bonding between ethanol molecules than between water molecules, thus
less energy is needed to vaporize ethanol than water. That’s why water has higher boiling point than ethanol.
21. How will you distinguish between methanol and ethanol by one test?
Ethanol gives iodoform with iodine in presence of sodium hydroxide. formation of yellow crystals indicate
that alcohol is ethanol. Whereas Methanol does not give iodoform test.
C2H5OH + 4I2 + 6NaOH CHI3 + HCOONa + 5NaI + 5H2O
CH3OH + I2 + NaOH No yellow ppt.
22. Write any four uses of ethyl alcohol.
Uses of Ethanol are as follows;
(i) It is used as solvent
(ii) It is used as a drink
(iii) It is used as a fuel
(iv) It is used as a preservative for biological specimen.
23. What is denaturing of alcohols?
Sometimes to avoid the use of ethanol for drinking, 10% methanol is added into it. This is called denaturing
of alcohol, also known as methylated spirit. A small quantity of pyridine or acetone may also be added for
this purpose.
24. How Lucas test is used to distinguish between primary secondary and tertiary alcohols?

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Primary, secondary and tertiary alcohols are identified and distinguished by reacting them with concentrated
HCl in anhydrous ZnCl2. An oily layer of alkyl halides separates out in these reactions as follows;
(i) Tertiary alcohols form an oily layer immediately.
R3C-OH + HCl R3C-Cl + H2O

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(ii) Secondary alcohols for an oily layer in 5 to 10 minutes primary.
R2CHOH + HCl R3CH-Cl + H2O
(iii) Primary alcohols form an oily layer only on heating.
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R-CH2 OH + HCl R-CH2-Cl + H2O
25. How phenol can be converted to benzene?
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Phenol can be converted into Benzene by the reduction with Zinc.

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Δ
+ Zn + ZnO
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26. How does phenol react with bromine water?

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An aqueous solution of phenol reacts with bromine water to give white ppts of 2,4,6-Tribromophenol.

27. What is Williamson’s synthesis?

Alcohols are reacted with metallic sodium to form alkoxides. this alkoxide ion is a strong nucleophile and
readily reacts with alkyl halide to produce an ether. This method is called Williamson’s synthesis.
2C2H5OH + 2Na 2C2H5O-Na+ + H2
C2H5O-Na+ + C2H5Br C2H5OC2H5 + NaBr
28. Ethanol gives different products with conc. H2SO4 under different conditions. Justify?
Ethyl Alcohol gives different products with conc H2SO4 on different temperatures;
At 180C with conc. H2SO4.
C2H5-OH CH2 = CH2 + H20
At 140C with conc. H2SO4.
2C2H5-OH C2H5-O-C2H5 + H20

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