Aldehydes Ketones and Carboxylic Acids Test

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Aldehydes Ketones and Carboxylic Acids Test - 11

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Weekly Quiz Competition

Question 1
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The compound formed as a result of oxidation of ethyl benzene by KMnO$$_{4}$$ is:

A
benzophenone

B
acetophenone

C
benzoic acid

D
benzyl alcohol

Solution

The compound formed as a result of oxidation of ethyl benzene by alkaline KMnO$$_{4}$$ is benzoic acid.

Other reagents that can be used are acidified potassium dichromate or dilute nitric acid.

Option C is correct.
Question 2
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Which one of the following undergoes reaction with $$50\%$$ sodium hydroxide solution to give the corresponding alcohol and acid?

A
Phenol

B
Benzaldehyde

C
Butanal

D
Benzoic acid

Solution

Benzaldehyde undergoes reaction with 50% sodium hydroxide solution to give benzyl alcohol and benzoic acid.
$$PhCHO \xrightarrow {NaOH} PhCOONa + PhCH_2OH$$.
This is an example of Cannizzaro Reaction which is a redox disproportionation reaction.
Question 3
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In the following sequence of reactions $$Toluene \xrightarrow{KMnO_4} A \xrightarrow{SOCl_2} B \xrightarrow[BaSO_4]{H_2/ Pd}C$$; then product $$C$$ is:

A
$$C_6H_5COOH$$

B
$$C_6H_5CH_3$$

C
$$C_6H_5CH_2OH$$

D
$$C_6H_5CHO$$

Solution

The oxidation of toluene with $$KMnO_4$$ gives benzoic acid.

Thionyl chloride converts carboxylic group to acid chloride.

Reaction with hydrogen in presence of palladium and barium sulphate gives benzaldehyde.

Option D is correct.
Question 4
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The IUPAC name of the following compound is :
$$H_{ 3 }C-\overset { \overset { CH_{ 3 } }{ | } }{ C } H-\overset { \overset { OH }{ |} }{ C }H -CH_2-COOH$$

A
2-Methyl-3-hydroxypentan-5-oic-acid

B
4,4-Dimethyl-3-hydroxy butanoic acid

C
3-Hydroxy-4-methylpentanoic acid

D
4-Methyl-3- hydroxypentanoic acid

Solution

Solution:- (C) $$3$$-Hydroxy-$$4$$-methylpetanoic acid
$$\underset { 5 }{ C } H_{ 3 }-\overset { \overset { CH_{ 3 } }{ | } }{ \underset { 4 }{ C } } H-\underset { \underset { OH }{ | } }{ \overset { 3 }{ C } } H-{ \overset { 2 }{ C } H_{ 2 } }-\overset { 1 }{ C } OOH$$

Question 5

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Directions For Questions

Columns 1, 2 and 3 contain starting materials, reaction conditions, and type of reactions, respectively.

Column I	Column 2	Column 3
(I) Toluene	(i) $${NaOH}/{{Br}_{2}}$$	(P) Condensation
(II) Acetophenone	(ii) $${{Br}_{2}}/{hv}$$	(Q) Carboxylation
(III) Benzaldehyde	(iii) $${{\left(C{H}_{3}CO\right)}_{2}O}/{C{H}_{3}COOK}$$	(R) Substitution
(IV) Phenol	(iv) $${NaOH}/{C{O}_{2}}$$	(S) Haloform

...view full instructions

For the synthesis of benzoic acid, the only correct combination is:

(I) (iv) (Q)

(III) (iv) (R)

(IV) (ii) (P)

(II) (i) (S)

Solution

For the synthesis of benzoic acid, the only CORRECT combination is (II) Acetophenone (i) $${NaOH}/{{Br}_{2}}$$ (S) Haloform

In haloform reaction, methyl ketones are oxidised to the sodium salt of carboxylic acid. The by-product is haloform.

$$\displaystyle Ph-COCH_3 + 3NaOBr \xrightarrow [\Delta ]{{NaOH}/{{Br}_{2}}} Ph-COONa + CHBr_3 +2NaOH$$

Hence, the correct option is $$\text{D}$$

Question 6

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Directions For Questions

Columns 1, 2 and 3 contain starting materials, reaction conditions, and type of reactions, respectively.

Column I	Column 2	Column 3
(I) Toluene	(i) $${NaOH}/{{Br}_{2}}$$	(P) Condensation
(II) Acetophenone	(ii) $${{Br}_{2}}/{hv}$$	(Q) Carboxylation
(III) Benzaldehyde	(iii) $${{\left(C{H}_{3}CO\right)}_{2}O}/{C{H}_{3}COOK}$$	(R) Substitution
(IV) Phenol	(iv) $${NaOH}/{C{O}_{2}}$$	(S) Haloform

...view full instructions

The only correct combination in which the reaction proceeds through radical mechanism is:

(III) (ii) (P)

(I) (ii) (R)

(IV) (i) (Q)

(II) (iii) (R)

Solution

The only correct combination in which the reaction proceeds through radical mechanism is (I) toluene (ii) $${{Br}_{2}}/{hv}$$ (R) substitution.

$$Br_2\xrightarrow{h\nu}2Br^{.}$$

$$\displaystyle C_6H_5-CH_3 \xrightarrow {{{Br}_{2}}/{hv}} C_6H_5-CH_2Br \xrightarrow {{{Br}_{2}}/{hv}} C_6H_5-CHBr_2 \xrightarrow { {{Br}_{2}}/{hv}} C_6H_5-CBr_3 $$

Hence, the correct option is $$\text{B}$$

Question 7
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Cyclohexene is best prepared from cyclohexanol by which of the following:

A
conc. $$\mathrm{H}_{3}\mathrm{P}\mathrm{O}_{4}$$

B
conc. $$\mathrm{H}\mathrm{C}l/\mathrm{Z}\mathrm{n}\mathrm{C}1_{2}$$

C
conc. HCl

D
conc. HBr

Solution

Cyclohexene is best prepared from cyclohexanol by using conc. $$H_3PO_4$$.
Question 8
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In the following sequence, products $$I, J$$ and $$L$$ are formed. $$K$$ represents a reagent. The structures of compounds $$J$$ and $$K$$ respectively are:

A

B

C

D

Solution

$$\underset {\text {Hex-3-ynal}}{CH_3-CH_2-C \equiv C-CH_2-CHO} \xrightarrow [2.PBr_3] {1. NaBH_4} \underset {\text {I}}{CH_3-CH_2-C \equiv C-CH_2-CH_2Br}$$

$$\xrightarrow [3. H_3O^+] {1. Mg/ether, 2. CO_2 } \underset {\text {J}}{CH_3-CH_2-C \equiv C-CH_2-CH_2-COOH} \xrightarrow {K=SOCl_2} CH_3CH_2C\equiv CCH_2CH_2COCl$$

$$ \xrightarrow [Pd/ BaSO_4, quinoline] {H_2}\underset {\text {L}}{CH_3-CH_2-C\equiv C-CH_2-CH_2-CHO} $$

$$Explanation:$$ Hex-3-ynal on reduction with sodium borohydride produces alcohol. The $$-OH$$ group of the alcohol reacts with phosphorus tribromide to form alkyl bromide (compound $$I$$).

The alkyl bromide reacts with $$Mg$$ to form alkyl magnesium bromide (Grignard reagent) which attacks carbon dioxide followed by hydrolysis to form a carboxylic acid (compound $$J$$).

It reacts with thionyl chloride (compound $$K$$) to form acid chloride which on hydrogenation with $$Pd$$ supported on barium sulphate partially poisoned with quinoline to form compound $$L$$.
Here, a triple bond is selectively reduced to a double bond.

Hence, the structures of compounds $$J$$ and $$K$$ respectively are represented by option $$A$$.
Question 9
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Find the product of the given reaction:

A

B

C

D

Solution
Question 10
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$$(1)$$ $$C_6H_5-\overset{O}{\overset{||}{C}}-C_6H_5$$
$$(2)$$ $$C_6H_5-CHO$$
$$(3)$$ $$p-CH_3-C_6H_4-CHO$$
$$(4)$$ $$p-CH_3O-C_6H_4-CHO$$

Correct order for nucleophilic addition reaction.

A
$$2 > 1 > 3 > 4$$

B
$$4 > 3 > 2 > 1$$

C
$$2 > 3 > 4 > 1$$

D
$$4 > 2 > 3 > 1$$

Solution

Reactivity of carbonyl compounds towards nucleophilic addition reaction depends on the presence of substituted group. Aldehydes are more reactive than ketone for nucleophilic addition reaction.

Electron withdrawing $$\left( -I, -M \right)$$ group increased reactivity towards nucleophilic addition reaction.

As the $$-OCH_3$$ and $$CH_3$$ groups shows $$+R$$ and $$+I$$ effect hence the reactivity decreases.

Thus the correct order is-
$$2 > 3 > 4 > 1$$