Question

Question. Using any necessary reagents, show how you would accomplish the following syntheses.

Short answer

The given reactant undergoes a reaction with concentrated sulfuric acid and concentrated nitric acid which introduces nitro group at para position of methyl group, this is due to directive influence of methyl group. Further, on reduction with iron and hydrogen chloride mixture, nitro group gets reduced to amino group. On treatment with cyclohexanoyl chloride, acetylation of amino group takes place and required product gets obtained.

Formation of the product

Step-by-step solution

Step-1. Explanation of part (a):

The given reactant undergoes a reaction with concentrated sulfuric acid and concentrated nitric acid which introduces nitro group at para position of methyl group, this is due to directive influence of methyl group. Further, on reduction with iron and hydrogen chloride mixture, nitro group gets reduced to amino group. On treatment with cyclohexanoyl chloride, acetylation of amino group takes place and required product gets obtained.

Formation of the product

Step-2. Explanation of part (b):

Aniline on reaction with 4-methylbenzenesulfonyl chloride produces a required product with removal of hydrogen chloride as side product.

Formation of the product

Step-3. Explanation of part (c):

The given reactant undergoes Hofmann exhaustive methylation in which excess of methyl iodide is used followed by treatment with silver oxide and heat which gives least substituted alkene as the major product.

Formation of the product

Step-4. Explanation of part (d):

Hydroxylamine is used to produce oximes from aldehydes and ketone. The given carbonyl reactant on treatment with hydroxylamine forms ketoxime which further on reaction with lithium aluminum hydride gets reduced to amino group and leads to formation of the required product.

Formation of the product

Step-5. Explanation of part (e):

The given reactant on treatment with hydrogen peroxide undergoes oxidation reaction and forms amine oxide and forms the required product. Amine oxides decompose when strongly heated and these do not undergo rapid inversion at the nitrogen atom.


Formation of the product

Step-6. Explanation of part (f):

For the oxidation of tertiary amine, reagents such as hydrogen peroxide or peroxycarboxylic acids can be used which gives amine oxides. The given reactant on treatment with hydrogen peroxide forms amine oxide which further on heating gives alkene as the product.


Formation of the product

Step-7. Explanation of part (g):

Carboxylic acids react with thionyl chloride to form acid chlorides. The given reactant has carboxylic group which on treatment with thionyl chloride gets converted to acid chloride and further reaction with secondary amine gives the required product as amino group acts as a nucleophile and attacks at carbonyl carbon which is an electrophile.

Formation of the product

Step-8. Explanation of part (h):

Carboxylic acids react with thionyl chloride to form acid chlorides. The given reactant has carboxylic group which on treatment with thionyl chloride gets converted to acid chloride and further reaction with secondary amine gives the required product as amino group acts as a nucleophile and attacks at carbonyl carbon which is an electrophile.

Formation of the product