Question

Match the compounds given in List-I and select the suitable option using the code given below:

List-I	List-II
(a) Benzaldehyde	(i) Phenolphthalein
(b) Phthalic anhydride	(ii) Benzoin condensation
(c) Phenyl benzoate	(iii) Oil of wintergreen
(d) Methyl salicylate	(iv) Fries arrangement

A. (a)-(iv), (b)-(i), (c)-(iii), (d)-(ii)
B. (a)-(iv), (b)-(ii), (c)-(iii), (d)-(i)
C. (a)-(ii), (b)-(iii), (c)-(iv), (d)-(i)
D. (a)-(ii), (b)-(i), (c)-(iv), (d)-(iii)

Answer 1

. To find the appropriate matching of the two lists given in the question, try to describe each option given in the list. For example, about the benzoin condensation and Fries arrangement, try to explain about it and see what compounds undergo this process. Likewise, go through each option.

Complete step by step answer:
To solve such questions, we need to usually cross check each option that is given in the two lists. So, let us cross check each option from both the lists.
So, coming to the option given in list-II, benzoin condensation reaction can be defined as the reaction between two kinds of aromatic aldehydes especially benzaldehyde, in the presence of some catalyst (either a nucleophile or a heterocyclic group) to form an aromatic parent compound. So, in case of benzaldehyde, two molecules of benzaldehyde react with cyanide ions (acts as catalyst) to form benzoin. Thus, benzaldehyde matches with benzoin condensation.

Now coming to Fries arrangement, Fries rearrangement is an organic rearrangement in which an aryl ester is transformed into a hydroxyl aryl ketone with the help of a Lewis acid catalyst and an aqueous acid. And here in the given question, we can see that phenyl benzoate is an aryl ester. So, when it is heated with anhydrous aluminium chloride (a Lewis acid catalyst); a mixture of ortho and para hydroxy benzophenone (which is an aryl ketone) is formed. Therefore, option (c) matches with (iv) from list-II.
Now, coming to methyl salicylate, with chemical formula ${{C}_{8}}{{H}_{8}}{{O}_{3}}$, is an ester of salicylic acid and is also known as Oil of wintergreen. Therefore, this option matches with the oil of wintergreen.

Now, coming to option (b), in acidic medium, one molecule of phthalic anhydride condenses with two molecules of phenol to give one molecule of Phenolphthalein (is used as an acid-base indicator).
So, the correct match is (a)-(ii), (b)-(i), (c)-(iv), (d)-(iii).
So, the correct answer is “Option D”.

Note: It is important to note that Fries rearrangement is ortho and para selective, i.e. the acyl group attaches itself at the ortho and para positions of the aryl ring. Methyl salicylate has a sweet smell and is a member of the aspirin family and is widely used as a counter irritant. Phenolphthalein is a chemical indicator used to indicate the end point of the titration process and detect whether a solution is acid or base.