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Esters, Ethers and Amines

An ether A ...

Question

An ether $A$ $(C_{5} H_{12} O)$ when heated with excess of hot concentrated $H I$ produced two alkyl halides which on hydrolysis from compounds $B$ and $C$ . Oxidation of $B$ gives an acid $D$ whereas oxidation of $C$ gave a ketone $E$ . Deduce the structures of $A, B, C, D$ and $E$ .

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Solution

It is obvious from the given information that $B$ must be a primary alcohol while $C$ must be secondary alcohol. From there, it is quite easy to back calculate and derive the structure of the ether $A$ in the following way.

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Q. An ether [A],

C_{5} H_{12} O,

When heated with excess of hot concentrated

H I

produced two alkyl halides which when reacting with aqueous

N a O H

yield compounds [B] and [C]. Oxidation of [B] and [C] gave a propanone and an ethanoic acid respectively. The IUPAC name of the ether [A] is :

Q. A neutral organic compound A has formula

C_{9} H_{16} O_{3}

and rotates plane polarized light. A on acid hydrolysis produces B and

C (C_{3} H_{8} O)

. C on partial oxidation with PCC gives

D (C_{3} H_{6} O)

which does not give iodoform test. D on treatment with dilute solution of

N a O H

E (C_{6} H_{12} O_{2})

which is diastereomeric. E on treatment with the acidic solution of

K M n O_{4}

produces B. Deduce structures of A to E.

Q. An organic lactum A on acid hydrolysis produces B, an amino acid,.B on treatment with nitrous acid gives C. C on heating with concentrated

H_{2} S O_{4}

produces a lactone D. A can be synthesized by the reaction of cyclopentanone with hydroxylamine followed by treatment of product with concentrated

H_{2} S O_{4}

. Deduce structures of A to D.

(C_{4} H_{8} O)

, which undergoes haloform reaction gives compound B on reduction. B on heating with sulphuric acid gives a compound C which forms mono-ozonide D. D on hydrolysis in presence of zinc dust gives only acetaldehyde E. Identify A, B, C, D and E. Write the reactions involved.

Q. An organic compound

A (C_{9} H_{8} O_{3})

does not react with an aqueous solution of

N a H C O_{3}

and does not change the color of litmus paper. A on acid hydrolysis gives

B (C_{9} H_{8} O_{4})

whereas A on treatment with methanol in acid medium gives

C (C_{10} H_{14} O_{4})

as the major alcoholysis product. B on heating with excess of soda-lime produces toluene. Deduce structures of A to C.

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