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Unit-11
ALCOHOL PHENOL ETHER

1. Explain why:
a. Phenol has smaller dipole moment than methanol.
b. Grignard reagents soluble in ether but not in benzene.
c. Alcohols are easily protonated than phenols.
d. Di-tert butyl ether cannot be made by Williamson’s synthesis.
e. Ethers are cleaved by acids not by based.
f. Phenols do not undergo substitution of the — OH group like alcohols.
g. Alcohols acts as weak bases.
h. While separating a mixture of ortho and para-nitro phenols by steam distillation, name the isomer
which will be steam volatile. Give reasons
i. The carbon-oxygen bond in phenol is slightly stronger than that in methanol. Why?
j. Alcohols and ethers of comparable molecular mass have different boiling points.
k. C – O – H bond angle in alcohols slightly less than the tetrahedral angle whereas the
C – O – C bond angle in ether is slightly greater?
l. In Kolbe’s reaction, instead of phenol, phenoxide ion is treated with carbon dioxide. Why?
m. Explain why is O = C = O nonpolar while R – O – R is polar.
n. Ortho-nitrophenol is more acidic than ortho-methoxyphenol. Why?
o. Explain why Lewis acid is not required in bromination of phenol?

2. Kartick went to a sugar producing factory. He noticed an alcohol producing


unit associated with it. Generally alcohol is prepared industrially in places where
sugar is extracted from sugarcane.
a. As a student of chemistry can you tell Why?
b. What is Denatured alcohol?
c. Arrange water, ethanol and, phenol in increasing order of acidity and give reason for your
answer.

3. Water is a universal solvent. But alcohol also dissolves most of the substances soluble in water.
Boiling point of water is 100oC and that of alcohol is 80oC. The specific heat of water is much higher
than the specific heat of alcohol.
a. List out two possible differences if instead of water as the liquid in our body we had alcohol.
b. Name the starting material used in the industrial preparation of phenol.
c. Write complete reaction for the bromination of phenol in aqueous and non-aqueous medium.

4. Recently Bangalore Police launched a special drive to curb the crimes and accidents related to
“Drunken-Driving” An instrument known as “Alcometer” is used to test whether a driver has consumed
alcohol or not.

(i) Write the name and chemical formula of the compound used in alcometer.
(ii) Write the chemistry involved in the above test.
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5. Ravi Prasad, a farmer has 25 acres of land. He noticed some infection on the leaves of his crops. He
called his friend Raghav, who advised him to use DDT. However, Ravi Prasad preferred to use dry
powder of neem leaves as an insecticide.

(a) Mention reason why Ravi Prasad prefer using neem powder?
b) Draw the structure of DDT.
c) Write full form of DDT.

6. An owner of a paint company who was using ethanol as solvent noted that his stock of ethanol was
misused by his employee. To prevent this misuse, he decided to add small amount of a blue colour
compound (A) and another nitrogen containing heterocyclic base (B) which gives a foul smell to
alcohol.
a) Write the names of compound A& B ?
b) Name process of adding compound A & B to ethanol ?

7. Write the structures of the compounds whose names are given below :
(i) 3, 5-dimethoxyhexane-1, 3, 5-triol
(ii) cyclohexylmethanol
(iii) 2-ethoxy-3-methylpentane
(iv) 3-chloromethylpentan-2-ol
(v) p-nitroanisole

8. Describe the following reactions with example:


(i) Hydroboration oxidation of alkenes
(ii) Acid catalysed dehydration of alcohols at 443K.
(iii) Williamson synthesis
(iv) Reimer-Tiemann reaction.
(v) Kolbe’s reaction
(vi) Friedel-Crafts acylation of Anisole.

9. What happens when :


(i) aluminium reacts with tert-butyl alcohol
(ii) phenol is oxidised with chromic acid
(iii) cumene is oxidised in the presence of air and the product formed is treated with dilute acid.
(iv) phenol is treated with conc. HNO3
(v) phenol is treated with chloroform in presence of dilute NaOH.

10. How will you convert


(i) propene to propan-l-ol.
(ii) anisole to phenol
(iii) butan-2-one to butan-2-ol
(iv) ethanal to ethanol
(v) phenol to ethoxybenzene
(vi) 1-phenylethene to 1-phenylethanol
(vii) formaldehyde to cyclohexylmethanol
(viii) butyl bromide to pentan-1-ol.
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(ix) toluene to benzyl alcohol


(x) 1-propoxypropane to propyl iodide
(xi) ethyl bromide to 1-ethoxyethane
(xii) methyl bromide to 2-methoxy-2-methylpropane
(xiii) ethyl bromide to ethoxybenzene
(xiv) ethanol to benzyl ethyl ether.

11. Write steps to carry out the following conversion:


a. phenol to aspirin
b. propan-2-one to tert-butyl alcohol
c. ethanol to ethene
d. ethane-1, 2-diol from ethanol
e. acetophenone from phenol
f. phenol from benzene
g. Propene to propan-2-ol
h. Ethyl magnesium chloride to propan-1-ol.
i. Methyl magnesium bromide to 2-methylpropan-2-ol
j. Picric acid from phenol
k. Propene to Propane-1-ol
l. Ethanal to Propan-2-ol
m. Ethyl chloride to Ethanal
n. Phenol to benzoquinone
o. toluene obtained from phenol
p. Phenol to anisole
q. Propan-2-ol to 2-methylpropan-2-ol
r. Aniline to phenol

12. Complete the following reaction:


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