Alcohols Phenols and Ethers Test

Result

Alcohols Phenols and Ethers Test - 60

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Weekly Quiz Competition

Question 1
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Ethanol $$\xrightarrow{PBr_3}X\xrightarrow{alc.KOH}Y\xrightarrow[(ii)H_2O,Heat]{(i)\;H_2SO_4\;room\;temperature}Z$$;
The product $$ Z$$ in the above reaction is:

A
$$CH_3CH_2\!-\!OH$$

B
$$CH_2 = CH_2$$

C
$$CH_3CH_2\!-\!O\!-\!CH_2CH_3$$

D
$$CH_3CH_2\!-\!O\!-\!SO_3H$$

Solution

When ethanol reacts with $$PBr_3$$ it undergoes substitution reaction to form ethyl bromide as a product.
This ethyl bromide when reacts with $$alc.$$ $$KOH$$, it undergoes $$\beta$$-elimination reaction to form ethene.
This ethene on reaction with sulphuric acid undergoes sulphonation followed by hydration to form ethanol as a product.
Question 2
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The above shown benzyl alcohols are made to react with $$HBr$$. The least reactive and the most reactive are respectively :

A
1 and 4

B
2 and 3

C
2 and 4

D
1 and 3

Solution
Question 3
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Which of the following will be the correct product (P) for the given reaction?

A

B

C

D

Solution

Dehydration of alcohol involves the formation of carbocation which further undergoes rearrangement as the tertiary carbocation is more stable than secondary carbocation, which then accepts the electron from $$\pi$$ bond of cyclohexene and forms bicyclic compound.

Option C is correct.
Question 4
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$$Propan-1-ol$$ can be prepared from propene by :

A
$$H_2O / H_2SO_4$$

B
$$Conc. H_2SO_4$$

C
$$B_2H_6$$ followed by $$H_2O_2/OH$$

D
$$CH_3CO_2H / H_2SO_4$$

Solution
Question 5
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Decreasing order of acidity is:

A
I > III > II > IV > V

B
IV > I > II > III > IV

C
IV > III > I > II > V

D
IV > V > III > I > II

Solution
Question 6
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$$A\:(C_7H_8O)+Na/\Delta\longrightarrow$$ No gaseous product
$$A+Br_2/FeBr_3\longrightarrow\:C_7H_7OB_r$$ (Two isomers)
$$A$$ can be:

A

B

C

D

Solution

When compound A is heated with sodium no gaseous product is obtained.
When phenol is heated with sodium, hydrogen gas is evolved.
Thus presence of phenolic OH group is ruled out. Thus options A, B and C are ruled out.
Option D (anisole) is the correct answer.
Anisole on bromination with bromine in presence of ferric bromide gives two isomers ortho and para bromo derivatives of anisole.
Question 7
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Directions For Questions

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Identify the structure of A:

A
$$CH_3 - CH_2 - CH_2 - \underset{\!\!\!OH}{\underset{\!\!\!\!\!\!|}{CH}} - CH_3$$

B
$$(CH_3)_2CHCHOHCH_3$$

C
$$(CH_3)_3C-CH_2-OH$$

D
$$CH_3 - CH_2 - \underset{\!\!\!OH}{\underset{\!\!\!\!\!|}{CH}} - CH_2 - CH_3$$

Solution

The structure of A in the following reaction is option B.
Question 8
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Which of the following reaction is most exothermic?

A

B

C

D
$$\overset{\bullet}{C}H_3 + CH_3CH_2CH_3 \rightarrow CH_4 + CH_3 \overset{\bullet}{C}HCH_3$$

Solution

The reactions involving the neutralization of an acid with a base are most exothermic reactions.
Thus, the neutralization of phenol with sodium hydroxide is highly exothermic.
Question 9
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Which of the following reagents should be used to prepare tert-butyl ethyl ether?

A
$$tert$$-butyl bromide and sodium ethoxide

B
$$tert$$-butyl alcohol and ethyl bromide

C
$$tert$$-butyl alcohol and ethanol

D
potassium $$tert$$-butoxide and ethyl bromide

Solution

$$tert$$-butyl ethyl ether can be prepared by the reaction of potassium $$tert$$-butoxide with ethyl bromide.

The process is Williamson synthesis.

This reaction follows $$S_{N}{2}$$ mechanism.

Option D is correct.
Question 10
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Which of the following is not a good method to prepare tert-butyl methyl ether?

A
$${(CH_3)}_3CO^{\displaystyle-}Na^{\displaystyle+}+CH_3Br\rightarrow$$

B
$${(CH_3)}_3CBr+CH_3O^{\displaystyle-}Na\rightarrow$$

C
$$H_2C=C{(CH_3)}_2+CH_3OH\xrightarrow{H^+}$$

D
All of these

Solution

In the presence of a strong base, such as sodium methoxide ion, tert-butyl bromide will undergo dehydrobromination to form 2-Methylprop-1-ene and not ether. Because the alkyl halide is tertiary which gives elimination reaction rather than substitution.

Hence, this is not a good method for the preparation of tert-butyl methyl ether.

Option B is correct.