ASSIGNMENT of Alcohol, Phenol and Ether

ASSIGNMENT
ALCOHOL, PHENOL AND ETHER
1.
Ans: (d)
2
Ans: (c)
3
Ans: (c)
4
Ans: (c)
5
Ans: (a)
6
Ans: (d)
The question given below consist of an Assertion and the Reason. Use the following key to choose the
appropriate answer.
(a) If both assertion and reason are CORRECT and reason is the CORRECT explanation of the assertion.
(b) If both assertion and reason are CORRECT, but reason is NOT the CORRECT explanation of the
assertion.
(c) If assertion is CORRECT but reason is INCORRECT.
(d) If assertion is INCORRECT but reason is CORRECT.
(e) If both assertion and reason are INCORRECT.
7. Assertion: The boiling point of alcohol is higher than those of hydrocarbons of comparable molecular
mass.
Reason: Alcohol show intramolecular hydrogen banding. Ans: (a)
8 Assertion: Reimer-Tiemann reaction of phenol with CCl4 in NaOH at 340 K gives salicylic acid as the major
product.
Reason: The reaction occurs through intermediate formation of dichlorocarbene. Ans: (d)
9 Match the compounds with their distinction test:
(A) Methanol and ethanol P. lucas reagent
(B) Phenol and cyclohexanol Q. Sodium metal
(C) n-propyl alcohol and tertbutyl alcohol R. Iodoform test
(D) Methanol and diethyl ether S. Ferric chloride
Ans: (d)
10 Match the column:
(A) Williamsons synthesis P. Conversion of phenol to salicylic acid
(B) Conversion of 2° alcohol to ketone Q. Conversion of phenol to salicaldehyde
(C) Reimer Tiemann reaction R. Heated with Cu-573k.
(D) Kolbe's reaction S. reaction of alkyl halide with sodium alkoxide
(a) A–S, B–R, C–Q, D–P
(b) A–R, B–S, C–Q, D–P
(c) A–R, B–Q, C–P, D–S
(d) A–Q, B–P, C–R, D–S Ans: (a)
11 Write the structures of the compounds whose names are given below:
(i) 3, 5-Dimethoxyhexane-1, 3, 5-triol (ii) Cyclohexyl methanol (iii) 2-Ethoxy-3-methylpentane
(iv) 3-Chloromethylpentan-2-ol (v) p-Nitro anisole
12 Describe the following reactions with example:
(i) Hydroboration oxidation of alkenes (ii) Acid catalyzed dehydration of alcohols at 443K.
(iii) Williamson synthesis (iv) Reimer-Tiemann reaction (v) Kolbe’s reaction (vi) Friedel-Crafts acylation of
Anisole
13 Complete the following reactions:
14 Assign reasons for the following:

(a) In Kolbe’s reaction, instead of phenol, phenoxide ion is treated with carbon dioxide. Why? Ans:
Due to high reactivity of electrophilic aromatic substitution towards phenoxide ion, phenoxide ion
is treated with carbon dioxide, instead of phenol, in Kolbe’s reaction.
(b) Why is the 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? Ans: Due to the repulsion between the unshared
pair of electrons or the lone pair of electrons on the oxygen atom, the C—O—H bond angle in
alcohols is slightly less than the tetrahedral angle.
(c) Alcohols have higher boiling points than ethers of comparable molecular mass. Ans: Due to inter
H-bond.
(d) Phenols are more acidic than alcohols. Ans: As conjugate base of phenol i.e., phenoxide is
resonance stabilised.
(e) The following is not an appropriate method for the preparation of t-butyl ethyl ether.
Ans: 3° alkyl halide follows SN1 reaction through

the formation of carbocation which undergoes elimination.
(f) Alcohols can act as weak base as well as weak acids.
(g) Alcohols undergo nucleophilic substitution reactions but phenols do not undergo nucleophilic
substitution at C–1 carbon.
15 (a) An organic compound ‘X’ when heated with Mg gave ‘Y’. ‘Y’ on treatment with CH3CHO followed
by acid hydrolysis gave 2-propanol. Identify the compound ‘X’. What is ‘Y’ known as? Ans: X =
CH3Br, Y = CH3MgBr
(b) An alcohol A (C4H10O) on oxidation with acidified K2Cr2O7 gives carboxylic acid ‘B’ (C4H8O2).
Compound ‘A’ when dehydrated with conc. H2SO4 at 443 K gives compound ‘C’. On hydration with
aqueous H2SO4 . ‘C’ gives compound ‘D’ (C4H10O) which is an isomer of ‘A’. Compound ‘D’ is
resistant to oxidation but compound ‘A’ can be easily oxidized. Identify A, B, C and D and write
their structure.
(c) m
16 Give the mechanism of:
(a) Write mechanism of reaction of HI with methoxymethane.
(b) Dehydration of ethanol in presence of conc. H2SO4
(c) Hydration of ethene in the presence of conc.H2SO4
17 Arrange the following in the increasing order of property shown:
a. Methanol, Ethanol, Diethyl ether, Ethylene-glycol. (Boiling points)
b. Phenol, o-nitrophenol, m-nitrophenol, p-nitrophenol. (Acidic strength)
Acidic strengths of isomeric phenols: (i) Phenols having electron withdrawing groups p > o > m. (ii)
Phenols having electron donating group m > p > o
c. Pentan-1-ol, n-butane, pentanal, ethoxyethane (Boiling point)
18 Give a chemical test to distinguish between the following pair of compounds.
(i) n-Propyl alcohol and isopropyl alcohol (ii) Methanol and ethanol (iii) Cyclohexanol and phenol. (iv)
Propan-2-ol and 2-methylpropan-2-ol. (v) Phenol and anisole (vi) Ethanol and diethyl ether
19 Name the reagents used in the following reactions:
(i) Oxidation of a primary alcohol to carboxylic acid. (ii) Oxidation of a primary alcohol to aldehyde. (iii)
Bromination of phenol to 2,4,6-tribromophenol. (iv) Benzyl alcohol to benzoic acid (v) Phenol to Benzene
20 How are the following conversions carried out? (i) Ethyl magnesium chloride to Propan-1-ol. (ii) Methyl
magnesium bromide to 2-Methylpropan-2-ol (iii) Propene to propan-2-ol (iv) Propan-2-ol to propanone
(v) Benzyl chloride to benzyl alcohol?
21 Write the names of reagents and equations for the preparation of the following ethers by Williamson’s
synthesis: (i) 1-Propoxypropane (ii) Ethoxybenzene (iii) 2-Methoxy-2-methylpropane (iv) 1-Methoxyethane
22 Write equations of the following reactions: (i) Friedel-Crafts reaction – alkylation of anisole. (ii) Nitration
of anisole. (iii) Bromination of anisole in ethanoic acid medium. (iv) Friedel-Craft’s acetylation of anisole.
23 Explain the fact that in aryl alkyl ethers (i) the alkoxy group activates the benzene ring towards
electrophilic substitution and (ii) it directs the incoming substituents to ortho and para positions in
benzene ring
24 Write the equation of the reaction of hydrogen iodide with: (i) 1-propoxypropane (ii) methoxybenzene
and (iii) benzyl ethyl ether.
25 Give the IUPAC name of the following compounds:

ASSIGNMENT of Alcohol, Phenol and Ether

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ASSIGNMENT

ALCOHOL, PHENOL AND ETHER

14 Assign reasons for the following:

Ans: 3° alkyl halide follows SN1 reaction through

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