Question Set B

Hydroxy Compounds and Ethers

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Questions:

Multiple Choice Question

13 x 1 = 13

Intermolecular hydrogen bonds are not _______ present in.

(a)

CH₃COOH

(b)

C₂H₅OC₂H₅

(c)

CH₃CH₂OH

(d)

C₂H₅NH₂

Identify the major product in the given reaction

(a)

(b)

(c)

(d)

In the following sequence of reaction, the end product 'B' is ________.

(a)

C₆H₅N₂CI

(b)

(c)

(d)

C₆H₅OH

CH₂= CH₂+H₂O The above reaction is _______.

(a)

Lucas test

(b)

Saponification

(c)

Victor Meyer's test

(d)

hydroxylation

Lower alcohols like ethanol and methanol are miscible in water due to _______.

(a)

their acidic character

(b)

vanderwaals force of attraction

(c)

dipole-dipole inter action

(d)

inter molecular hydrogen bonding

Which of the following has an offensive odour?

(a)

Phenol

(b)

Benzy lalcohol

(c)

Acrolein

(d)

Benzyl benzoate

Predict the structure of propane-1,2 diol ______.

(a)

CH₂ (OH) - CH₂CH₂OH

(b)

HOCH₂ - CH₂OH

(c)

CH₃CH (OH) CH₂OH

(d)

None of these

In the sequence of reactions Identify 'C'.

(a)

(b)

(c)

(d)

The above reaction is called ______.

(a)

Gattermann reaction

(b)

Williamson ether synthesis

(c)

Swern's reaction

(d)

Riemer tiemann reaction

10.

Pick out the odd one among the following.

(a)

CH₃ - CH - OH - CH₃

(b)

\({ CH }_{ 3 }{ CH }_{ 2 }-\underset { \overset { | }{ { CH }_{ 3 } } }{ CH } -OH\)

(c)

(CH₃)₃ - C - OH

(d)

C₆H₅ - CH - OH - C₂H₅

11.

One mole of an organic compound (A) with the formula C₃H₈O reacts completely with two moles of HI to form X and Y. When Y is boiled with aqueous alkali it forms Z. Z answers the iodoform test. The compound (A) is ______.

(a)

propan – 2-ol

(b)

propan -1-ol

(c)

ethoxy ethane

(d)

methoxy ehane

12.

(CH₃)₃-C-CH(OH) CH₃ \(\overset { con{ H }_{ 2 }{ SO }_{ 4 } }{ \longrightarrow } \)X (major product)

(a)

(CH₃)₃ CCH = CH₂

(b)

(CH₃)₂C = C (CH₃)₂

(c)

CH₂= C(CH₃)CH₂-CH₂- CH₃

(d)

CH₂= C (CH₃) - CH₂- CH₂- CH₃

13.

Which one of the following is the strongest acid.

(a)

2 - nitrophenol

(b)

4 – chlorophenol

(c)

4– nitrophenol

(d)

3 – nitrophenol

Assertion and reason

3 x 2 = 6

14.

Assertion: Compounds with two hydroxy groups are gem diols.
Reason: Ethanol which contains 5% methanol is known as methylated spirit.
Codes:
a) (A) and (R) are true and (R) is the correct explanation of (A)
b) Both (A) and (R) are true but (R) does not explain (A)
c) (A) is true but (R) is false
d) Both (A) and (R) are false

15.

Assertion: Ethanol is a weaker acid than phenol.
Reason: Sodium ethoxide may be prepared by the reaction of ethanol with aqueous NaOH.
Codes:
a) (A) and (R) are true and (R) is the correct explanation of (A)
b) Both (A) and (R) are true but (R) does not explain (A)
c) (A) is true but (R) is false
d) Both (A) and (R) are false

16.

Assertion: Phenol is more reactive than benzene towards electrophilic substitution reaction
Reason: In the case of phenol, the intermediate arenium ion is more stabilized by resonance
Codes:
a) if both assertion and reason are true and reason is the correct explanation of assertion.
b) if both assertion and reason are true but reason is not the correct explanation of assertion.
c) assertion is true but reason is false
d) both assertion and reason are false.

(a)

if both assertion and reason are true and reason is the correct explanation of assertion.

(b)

if both assertion and reason are true but reason is not the correct explanation of assertion.

(c)

assertion is true but reason is false

(d)

both assertion and reason are false.

Generic 3

3 x 3 = 9

17.

Complete the following sequence of reaction and Identify A, B and C.

18.

How is phenol prepared from
i) chloro benzene
ii) isopropyl benzene

19.

What is the major product obtained when two moles of ethyl magnesium bromide is treated with methyl benzoate followed by acid hydrolysis.

Generic 2

4 x 2 = 8

20.

State Saytzeff's rule.

21.

What happens when phenol is treated with diazonium chloride in presence of NaOH?

22.

Explain 'esterification' reaction with an example.

23.

Complete the following reactions

ii) \(C_6H_5-CH_{2}CH(OH)CH(CH_3)_2 \overset{ConH_2SO_4}\longrightarrow\)

One or Two Words / Correct Statement

1 x 1 = 1

24.

(a) Diethylether with chlorine in presence of sunlight forms (C₂Cl₅)₂O.
(b) The formula of diethyl oxonium chloride is (C₂H₂)₂-O⁺Cl^-.
(c) In anisole oxygen is strongly bonded to benzene ring.
(d) Ether is used as solvent for Grignard reagent

Find the wrong statement

1 x 2 = 2

25.

Pick out the wrong statement regarding ethers.
a) dimethyl ether and diethyl ehters are simple ethers
b) ethyl methyl ether is a symmetrical ether
c) the reaction between sodium ethoxide and methyl bromide is known as williamson's ether synthesis
d) Diethyl ether is used as an anaesthetiz.

Generic 5

2 x 5 = 10

26.

An organic compound (A) of molecular formula C₆H₆O gives violet colour with neutral FeCI₃. (A) gives maximum of two isomers (B) and (C) when an alkaline solution of (A) is refluxed with CCI₄ (A) also reacts with C₆H₅N₂CI to give the compound (D) which is red orange dye. Identify (A), (B), (C) and (D). Explain with suitable chemical reactions.

27.

An organic compound (A) (C₆H₆O) gives maximum of two isomers (B) and (C) When an alkaline solution of (A) is refluxed with chloroform. (B) on oxidation gives acid (D). The acid (D) is also obtained by I treating sodium salt of (A) with CO₂ under pressure followed by hydrolysis. Identify the compounds (A), (B), (C) and (D) and explain with proper chemical reactions.

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Answers Key:

Multiple Choice Question

13 x 1 = 13

(b)
C₂H₅OC₂H₅

(d)
C₆H₅OH

(d)
hydroxylation

(d)
inter molecular hydrogen bonding

(b)
Williamson ether synthesis

10.

11.

12.

(CH₃)₂C = C (CH₃)₂

13.

Assertion and reason

3 x 2 = 6

14.

b) Both (A) and (R) are true but (R) does not explain (A)

15.

c) (A) is true but (R) is false

16.

a) if both assertion and reason are true and reason is the correct explanation of assertion.

Generic 3

3 x 3 = 9

17.

A - CH₃I- Methyl Iodide
B - C₆H₅OH - Phenol
C - C₆H₅ONa - Sodium Phenoxide

18.

(i) Chloro benzene:
When Chlorobenzene is hydrolysed with 6-8% NaOH at 300 bar and 633K in a closed vessel, sodium phenoxide is formed which on treatment with dilute HCl gives phenol.

(ii) isopropyl benzene:
A mixture of benzene and propene is heated at 523K in a closed vessel in presence of H₃PO₄ catalyst gives cumene (isopropylbenzene). On passing air to a mixture of cumene and 5% aqueous sodium carbonate solution, cumene hydro peroxide is formed by oxidation. It is treated with dilute acid to get phenol and acetone. Acetone is also an important byproduct in this reaction.

19.

Generic 2

4 x 2 = 8

20.

During intramolecular dehydration, if there is a possibility to form a carbon-carbon double bond at different locations, the preferred location is the one that gives the more (highly) substituted alkene i.e., the stable alkene.

21.

Phenol couples with benzene diazonium chloride in an alkaline solution to form p-hydroxy azobenzene (a red orange dye).

22.

Alcohols react with carboxylic acids in the presence of an acid to give esters.

23.

(i)
n-Nitro benzoate (Major Product)

(ii)

One or Two Words / Correct Statement

1 x 1 = 1

24.

()
(b) The formula of diethyl oxonium chloride is (C₂H₂)₂-O⁺Cl^-.

Find the wrong statement

1 x 2 = 2

25.

ethyl methyl ether is a symmetrical ether

Generic 5

2 x 5 = 10

26.

(i) Compound A giving violet colour with neutral ferric chloride is phenol (C₆H₅OH).
(ii) (B) and (C) isomers are formed when alkaline solution of (A) is refluxed with CCI₄.

(iii) (A) when treated with C₆H₅N₂CI, forms a red orange dye (D).

Compound	Compound Name	Formula
A	Phenol	C₆H₅OH
B	o-Hydroxy benzoic acid
C	p-Hydroxy benzoic acid
D	p-Hydroxy azo benzene

27.

(i) When alkaline solution of (A) is refluxed with chloroform.isomers (B) and (C) are obtained

(ii) (B) on oxidation gives acid (D),

(iii) The acid (D) is also obtained by treating sodium salt of (A) with CO₂ under pressure followed by hydrolysis.