UNIT 07

ALCOHOLS, PHENOLS AND ETHERS

1 MARK QUESTIONS:

1) Write the IUPAC name of the following:

CBSE 2018
2) Write the IUPAC name of the following compound:

All India 2017

3) Write the IUPAC name of the given compound:

All India 2016

4) Write the IUPAC name of the given compound:

Delhi 2015
5) Write the IUPAC name of the given compound:

Foreign 2015
6) Which of the following isomers is more volatile: o-nitrophenol or p-nitrophenol?
Al 2014
7) Name the alcohol that is used to make the following ester.

AI 2014C
8) Write the IUPAC name of the following compound:

Foreign 2014
9) Of the two hydroxy organic compounds ROH and RꞌOH, the first one is basic and
other is acidic in behavior. How is R different from Rꞌ? Delhi 2013C
10) How is toluene obtained from phenol? Delhi 2013C
11) o-nitrophenol has lower boiling point than p-nitrophenol. Explain Delhi 2013C
12) How would you obtain ethane-1, 2-diol from ethanol? All India 2013C
13) Draw the structure of hex-1-en-3-ol compound. Delhi 2012
14) Draw the structural formula of 2-methylpropan-2-ol molecule. Delhi 2012
15) Write the IUPAC name of the following compound:

Foreign 2012
16) The C─O bond is much shorter in phenol than in ethanol. Give reason.
Delhi 2012C
17) How could you convert ethanol to ethane? All India 2011
18) Write the equations involved in the following reaction.
Reimer-Tiemann reaction (Or) All India 2012
Write Reimer-Tiemann reaction by giving an example. All India 2011
19) Draw the structure of 2, 6-dimethyphenol. All India 2011
20) Write the chemical equation for the preparation of phenol from benzene using
oleum and sodium hydroxide. Delhi 2011
21) Write the structure of the molecule of compound whose IUPAC name is 1-
phenylpropan-2-ol. All India 2020
22) Write the mechanism of acid dehydration of ethanol to yield ethane. (Or)
AI 2015C
Explain the mechanism of dehydration steps of ethanol.

Delhi 2015C, AI 2013

23) Write the IUPAC name of the following compound:

AI 2017
24) Write the IUPAC name of the following compound:

AI 2015
25) Write the equation involved in the reaction Williamson’s ether synthesis.
AI 2013
26) Write the IUPAC name of the following compound:

AI 2012C
27) Explain the following by one example: Friedel-Crafts acetylation of anisole.
Delhi 2011, 2010
28) Illustrate the following reaction by giving a chemical equation: Williamson’s
synthesis. Delhi 2010, AI 2010, Foreign 2010
 29) Phenyl methyl ether reacts with HI to give phenol and methyl iodide and not
iodobenzene and methyl alcohol. Why? Delhi 2010C

2 MARK QUESTIONS:

1) Write the mechanisms of the following SN1 reaction.

AI 2020
2) (i) Arrange the following compounds in the increasing order of their acidic
strength: p-cresol, p-nitrophenol, phenol.
(ii) Write the mechanism (using curved arrow notation) of the following reaction.

AI 2017
3) How are the following conversions carried out?
(i) Propene to propan-2-ol
(ii) Ethyl chloride to ethanal. Delhi 2014C
4) Write the mechanism of the following reaction.

Foreign 2014, Delhi 2014

5) How will you convert the following?
(i) Propan-2-ol to propanone
(ii) Phenol to 2,4,6-tribromophenol Delhi 2013
6) How will you convert?
(i) Propene to propan-1-ol
(ii) Ethanal to propan-2-ol Delhi 2013
7) How will you convert?
(i) Propene to propan-2-ol
(ii) Phenol to 2,4,6-tribromophenol Delhi 2013
8) Explain the mechanism of acid catalysed hydration of an alkene to form
corresponding alcohol. AI 2012
9) Explain the following behaviour.
(i) Alcohols are more soluble in water than the hydrocarbons of comparable
molecular masses.
(ii) Ortho-ntitrophenol is more acidic than ortho-methoxy phenol. AI 2012
10) How would you obtain?
(i) Picric acid from phenol?
(ii) 2-methyl propanol from 2-methyl propene? Delhi 2011
11) Account for the following:
(i) Propanol has higher boiling point than butane.
(ii) Ortho-ntitrophenol is more acidic than ortho-methoxy phenol. Delhi 2011C
12) Account for the following:
 (i) The boiling points of alcohols decrease with increase in branching of the
alkyl chain.
(ii) Phenol does not give protonation reaction readily. Delhi 2011C
13) How are the following conversions carried out?
(i) Benzyl chloride to benzyl alcohol
(ii) Methyl magnesium bromide to 2-methylpropan-2-ol. Delhi 2010
14) How are the following conversions carried out?
(i) Propene to propan-2-ol
(ii) Ethyl magnesium chloride to propan-1-ol Delhi 2010
15) Write the mechanism of hydration of ethane to ethanol. Foreign 2010
16) Give any chemical test to distinguish between the following pairs of
compounds.
(i) Phenol to benzoic acid.
(ii) 1-propanol and 2-propanol. Delhi 2010C
17) Write the equation for the preparation of 2-methyl-2-methoxypropane by
Williamson’s synthesis. AI 2020,2012C
18) Write the mechanisms of the following reaction. (Or)

Delhi 2016
Give mechanisms of preparation of ethoxy ethane from ethanol. Delhi 2013C
19) How is 1-propoxy propane synthesized from propan-1-ol? Delhi 2010
20) Define with examples:
(i) Reimer-Tiemann reaction.
(ii) Williamson’s Synthesis. AI 2019
21) Write the equations involved in the following reactions:
(i) Kolbe’s reaction.
(ii) Friedel-Crafts alkylation of anisole. AI 2019
22) Name the different reagents needed to perform the following reactions:
(i) Phenol to benzene.
(ii) Dehydration of propan-2-ol to propene.
(iii) Friedel-Crafts acetylation of anisole.
(iv) Dehydrogenation of ethanol to ethanal. Foreign 2014
23) Name the reagents used in the following reactions:
(i) Bromination of phenol to 2,4,6-tribromophenol.
(ii) Butan-2-one to butan-2-ol.
(iii) Friedel-Crafts alkylation of anisole.
(iv) Oxidation of primary alcohol to carboxylic acid. Foreign 2014
24) Name the reagents used in the following reactions:
(i) Nitration of phenol to2,4,6-trinitrophenol.
(ii) Butanal to butanol.
(iii) Friedel-Crafts acetylation of anisole.
(iv) Oxidation of primary alcohol to aldehyde. Foreign 2014
25) Write the equations involved in the following reactions:
 (i) Reimer-Tiemann reaction.
(ii) Williamson’s Synthesis. Delhi 2014
26) Write the equations involved in the following reactions:
(i) Williamson’s Ether Synthesis.
(ii) Kolbe’s reaction. Delhi 2014C

3 MARK QUESTIONS:

1) Write the product(s) of the following reactions:

(i) (ii)

(iii) AI 2020
2) Give the structures of final products expected from the following reactions:
(i) Hydroboration of propene followed by oxidation with H 2O2 in alkaline
medium.
(ii) Dehydration of (CH3)3C─OH by heating it with 20% H3PO4 at 358K.

(iii) Heating of with HI. Delhi 2020

3) How can you convert the following?
(i) Phenol to o-hydroxybenzaldehyde.
(ii) Methanal to ethanol.
(iii) Phenol to phenyl ethanoate. Delhi 2020
4) (i) How will you synthesis the following alcohol from appropriate alkene?

(ii) Write the mechanism of the following reaction.

AI 2019
5) (i) Show how will you synthesis the following alcohol by the reaction of a suitable
Grignard reagent on methanal?

(ii) Write the mechanism of the following reaction

All India 2019

6) (i) Butan-1-ol has a higher boiling point than diethyl ether. Why?
(ii) Write the mechanism of the following reaction:
 AI 2019
7) (i) Complete the following reaction and suggest a suitable mechanism for the

reaction:
(ii) Why ortho-nitrophenol is steam volatile while para-nitrophenol is less
volatile? 2018C
8) Predict the products of the following reactions:

(i)

(ii)

(iii) Foreign 2015

9) How are the following conversions carried out
(i) Benzyl chloride to benzyl alcohol?
(ii) Ethyl magnesium chloride to propan-1-ol?
(iii) Propene to propan-2-ol? All India 2015
10) (i) Write the mechanism of the following reaction

(ii) Write the equation involved in the Reimer-Tiemann reaction. All India 2014
11) How are the following conversions carried out?
(i) Propene to propan-2-ol
(ii) Ethyl magnesium chloride to propan-1-ol
(iii) Benzyl chloride to benzyl alcohol AI 2014C
12) Draw the structure and name the product formed if the following alcohols are
oxidized. Assume that an excess of oxidising agent is used.
(i) CH3CH2CH2CH2OH
(ii) 2-butanol
(iii) 2-methyl-1-propanol Delhi 2012
13) How would you obtain the following:
(i) Benzoquinone from phenol?
(ii) 2-methyl propan-2-ol from methyl magnesium bromide?
(iii) Propan-2-ol from propene? All India 2011, Foreign 2011
14) Account for the following:
(i) The boiling point of ethanol is higher than that of methanol.
(ii) Phenol is stronger acid than an alcohol.
(iii) Propanol has higher boiling point than butane. Delhi 2011C
15) (i) Describe the mechanism of hydration of ethene to yield ethanol.
(ii) Write Kolbe’s reaction with an example. AI 2011C
16) (i) Describe the mechanism of acid catalyzed dehydration of ethanol to yield
ethene. All India 2010C
(ii) Describe the chemical test to distinguish between ethanol and phenol.
17) State the products of the following reactions:
(i) CH3CH2CH2OCH3 + HBr →

(ii) All India 2012C

(iii) Foreign 2012

18) What happens when
(i) Phenol reacts with HNO3?
(ii) Ethyl chloride reacts with NaOC2H5?
Write the chemical equations involved in the above reactions. All India 2019
19) Write the main products in each of the following reactions:

(i)

(ii)

(iii) All India 2016

20) Write the final products in each of the following reactions:

(i)

(ii)

(iii) Delhi 2015

21) How do you convert the following
(i) Phenol to anisole?
(ii) Propan-2-ol to 2-methylpropan-2-ol?
(iii) Aniline to phenol? Delhi 2015
22) (i) Write the mechanism of the following reaction:

(ii) Write the equation involved in the acetylation of salicylic acid. Delhi 2015
23) Give reason for the following.
(i) Phenol is more acidic than methanol.
(ii) The C─O─H bond angel in alcohols is slightly less than the tetrahedral angle
(109◦ 28ꞌ).
(iii) (CH3)3C─O─CH3 on reaction with HI gives (CH3)3C─I and CH3─OH as the
main products and not (CH3)3C─OH and CH3─I. All India 2015
 24) Write the major product in the following equations:

(i)

(ii)
(iii) CH3─Cl + CH3CH2─ONa →? All India 2015C
25) Name the following according to IUPAC system.

(i)

(ii)

(iii) Delhi 2015C

26) How are the following conversions carried out?
(i) Propene to propan-2-ol.
(ii) Benzyl chloride to benzyl alcohol.
(iii) Anisole to p-bromoanisole. Delhi 2015C
27) Explain the following with an example for each:
(i) Kolbe’s reaction.
(ii) Reimer-Tiemann reaction.
(iii) Williamson ether synthesis. All India 2014C
28) Account for the following:
(i) The boiling points of ether are lower than isomeric alcohols.
(ii) Ortho-nitrophenol is more acidic than ortho-methoxy phenol.
(iii) Preparation of ethers by acid dehydration of secondary or tertiary alcohols is
not a suitable method. Delhi 2011C

5 MARK QUESTIONS:

1) (i) How do you convert the following?

a) Phenol to anisole.
b) Ethanol to propan-2-ol
(ii) Write mechanism of the following reaction:

(iii) Why phenol undergoes electrophilic substitution more easily than benzene?
Delhi 2019
2) (i) Account for the following:
a) o-nitrophenol is more steam volatile than p-nitrophenol.
b) Tert-butyl chloride on heating with sodium methoxide gives 2-
methylpropene instead of tert-butylmethylether.
(ii) Write the reaction involved in the following:
a) Reimer-Tiemann reaction.
b) Friedel-crafts alkylation of phenol.
(iii) Give simple chemical test to distinguish between ethanol and phenol.
Delhi 2019
3) (i) Write the products in the following reactions:

a)

b)
c)
(ii) Give simple chemical rests to distinguish between the following pairs of
compounds:
a) Ethanol and phenol.
b) Propanol and 2-methylpropan-2-ol. Delhi 2017
4) (i)Write the formula of reagents used in the following reactions:
a) Bromination of phenol to 2,4,6-tribromophenol.
b) Hydroboration of propene and then oxidation to propanol.
(ii) Arrange the following compounds in the increasing order of the property
indicated:
a) p-nitrophenol, ethanol, phenol (acidic character).
b) Propanol, propane, propanal (boiling point).
(iii) Write the mechanism (using curved arrow notation) of the following reaction:

Delhi 2017