Q38E - Organic Chemistry (Mcmurry)

Question

Draw structures corresponding to the following IUPAC names:

(a) Ethyl 1-ethylpropyl ether         (b) Di(p-chlorophenyl) ether

(c) 3,4-Dimethoxybenzoic acid    (d) Cyclopentyloxycyclohexane

(e) 4-Allyl-2-methoxyphenol (eugenol; from oil of cloves)

Step-by-Step Solution

Answer

The structures of the following given compounds are:

(a) 

Ethyl 1-ethylpropyl ether

(b) 

Di (p-chlorophenyl) ether

(c)

3,4-Dimethoxybenzoic acid

(d) 

Cyclopentyloxycyclohexane

(e) 

4-Allyl-2-methoxyphenol

Step-by-Step Solution Step 1: IUPAC names

The International Union of Pure and Applied Chemistry (IUPAC) refers to the systematic approach taken for the nomenclature of organic compounds. The IUPAC nomenclature of organic compounds essentially consists of three parts which are stem name, prefix, and suffix.

Step 2: structures of compound (a) and (b) ethers

(a) The given compound is Ethyl-1-ethylpropylether. It contains ether as the functional group mentioned in the suffix. There is also a central oxygen atom in Ethyl 1-ethylpropyl ether.

Ethyl 1-ethylpropyl ether

(b) In this structure, similarly, the IUPAC nomenclature of ethers is named in such a way that the two chloro- phenyl groups attached to the oxygen atom are named as chlorophenyl moieties as a prefix, and the word ether is added as a suffix.

Di (p-chlorophenyl) ether

Step 3: Structure of compound (c) acid

(c) The given compound is3,4-Dimethoxybenzoic acid. It contains acid as the functional group mentioned in the suffix, and two methoxy groups attached to the aromatic ring are named di-methoxy in the prefix.

3,4-Dimethoxybenzoic acid

Step 4: Structure of compound (d) alkane

(d) The given compound is Cyclopentyloxycyclohexane.It is named in such a way that the two cycloalkane groups attached to the oxygen atom are named Cyclopentyl moiety in the prefix and oxycyclohexane in the suffix.

Cyclopentyloxycyclohexane

Step 5: Structure of compound (e) alcohol

(e)The given compound is4-Allyl-2-methoxyphenol. It contains alcohol as the functional group mentioned in the suffix and one methoxy and one allyl group attached to the ring at ortho and para positions corresponding to the OH group.

4-Allyl-2-methoxyphenol