Alcohols Phenols and Ethers Test

Result

Alcohols Phenols and Ethers Test - 62

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Weekly Quiz Competition

Question 1
1 / -0

Which one of the following cannot be the product of the dehydration reaction of the above shown alcohol?

A

B

C

D

Solution

The reactions are given below. All the possible products are shown. Option C can not be formed.
Question 2
1 / -0

What is $$A$$ ?

A
$$ TsO-CH_2 - C \equiv CH$$

B
$$ TsO_2-CH_2 - C \equiv CH$$

C
$$ TsO-CH_2 - C - CH_3$$

D
none of the above

Solution

Catalytic p-toluenesulfonic acid $$(TsOH)$$ reacts as acid and gives elimination products with the formation of $$TsO-CH_2-C\equiv CH$$.
Question 3
1 / -0

Reactions I and II are limited mainly to naphthalene compounds. These reactions are called, respectively:

A
bucherer reaction and its reversal

B
bischler-Napieralski reaction and its reversal

C
birnbaum-Simonini reaction and its reversal

D
borodine-Hunsdiecker reaction and its reversal

Solution

The Bucherer reaction is the reversible conversion of a naphthylamine to a naphthol in the presence of an aqueous sulfite or bisulfite.
The reaction is given as shown above.
Question 4
1 / -0

Which of the following is the correct method for synthesizing methyl-t-butyl ether?

A
$$\displaystyle \left ( CH_{3} \right )_{3}CBr+NaOMe\rightarrow $$

B
$$\displaystyle \left ( CH_{3} \right )_{3}CONa+MeBr\rightarrow $$

C
$$\displaystyle \left ( CH_{3} \right )_{3}CBr+HOMe\rightarrow $$

D
Both A and B

Solution

In the synthesis of n-alkyl ter-alkyl ether by Williamson's method,
$$\displaystyle 1^{\circ}RX\:and\:3^{\circ} RONa$$ are used.

If $$\displaystyle 3^{\circ}RX$$ is used, it will undergo dehydrohalogenation to form alkene.

Hence, the correct method for synthesising methyl-t-butyl ether is:

$$\displaystyle \left ( CH_{3} \right )_{3}CONa+CH_3Br\rightarrow \left ( CH_{3} \right )_{3}COMe+NaBr$$
Question 5
1 / -0

When the given compound is treated with $${C}_{2}{H}_{5}MgBr$$ followed by hydrolysis, the product is:

A

B

C

D

Solution
Question 6
1 / -0

Give the decreasing order of reactivity of the following alkyl halides in the Williamson' s reaction.
i. $$\displaystyle \left ( CH_{3} \right )_{3}C-CH_{2}Br$$
ii. $$\displaystyle ClCH_{2}CH=CH_{2}$$
iii. $$\displaystyle ClCH_{2}CH_{2}CH_{3}$$
iv. $$\displaystyle BrCH_{2}CH_{2}CH_{3}$$

A
ii > iv > iii > i

B
i > iii > iv > ii

C
ii > iii > iv > i

D
i > iv > iii > ii

Solution

ii > iv > iii > i (ally chloride > $$\displaystyle RX=1^{\circ}RBr> 1^{\circ}>$$ neopentyl bromide. (R-Br) bond is weaker than (R-CI) bond. $$SN^{2}$$ reaction is faster with (R-Br) than with (R-CI).
Question 7
1 / -0

The product (B) is :

A

B

C

D
All

Solution

The cleavage of (C- OH) bond is feasible rather than cleavage of (Ar-OH) bond because of resonance stabilistion in ArOH.
Question 8
1 / -0

The compound (A) is:

A

B

C

D

Solution

Red $$P$$ and $$HI$$ is a traditional reducing agent to convert alcohols into alkanes. $$H_3PO_3$$ form in this reduction reaction. The product $$A$$ of reaction is cyclobutandicarboxylic acid.
Question 9
1 / -0

Which statement is correct for the conversion of $$ROH$$ to $$RX$$ by reagents $$(A)$$ $$ ( SOCl_{2},\ PBr_{3}$$ $$ PCl_{3}$$ $$ Pl_{3},\:TsCl )$$ compared to using $$HX$$?

A
No rearrangement occurs with predictable stereochemistry by reagents $$(A)$$

B
Reasgents $$(A)$$ are not useful for $$\displaystyle 3^{\circ}$$ alcohols, while $$HX$$ reacts easily with $$\displaystyle 3^{\circ}$$ alcohols involving no rearrangement.

C
Reagents $$(A)$$ must be used in anhydrous conditions because all react vigorously with $$\displaystyle H_{2}O$$ and they produce harmful gases $$\displaystyle \left ( SO_{2},HCl,HBr,\:and\:HI \right )$$

D
All of the above

Solution

All the three statements (A), (B) and (C) are correct. Hence, (D) is the correct option.

(A) No rearrangement occurs with predictable stereochemistry by reagents $$(A)$$. However if $$HX$$ is used, the rearrangement is possible.

(B) Reagents $$(A)$$ are not useful for tertiary alcohols, while $$HX$$ reacts easily with tertiary alcohols involving no rearrangement.

(C) Reagents $$(A)$$ must be used in anhydrous conditions because all react vigorously with $$H_2O$$ and they produce harmful gases ($$SO_2$$, $$HCl$$, $$HBr$$ and $$HI$$).

For example, phosphorous trichloride reacts with water to form orthophosphorous acid and $$HCl$$.

$$PCl_3 + 3H_2O \rightarrow P(OH)_3 + 3HCl$$
Question 10
1 / -0

Which statement is correct for the conversion of ROH to RX by reagents $$\displaystyle \left ( SOCl_{2},PBr_{3},PCl_{3},PI_{3} \right )$$ and TsCl compared to using HX?

A
No rearrangement occurs with predictable stereo-chemistry by reagents

B
Reagents are not useful for $$\displaystyle 3^{\circ}$$ alcohols, while HX reacts easily with $$\displaystyle 3^{\circ}$$ alcohols involving no rearrangement

C
Reagents must be used in anhydrous conditions because all react vigrously with $$\displaystyle H_{2}O$$ and they produce harmful gases ($$\displaystyle SO_{2}$$, HCl, HBr, and HI)

D
All

Solution

All the statements given in options A, B and C are correct for the conversion. Hence option D is correct.