Q32E - Organic Chemistry (Mcmurry)

Question

Draw structures corresponding to the following IUPAC names:

a)cis-1,2-Cyclohexanedicarboxylic acid

b) Hepatanedioic acid

c) 2-Hexen-4-ynoic acid

d) 4-Ethyl-2-propyloctanoic acid

e) 3-chlorophthalic acid

f) Triphenylacetic acid

g) 2-Cyclobutenecarbonitrile

h) m-Benzoylbenzonitrile

Step-by-Step Solution

Answer

a) The structure of cis-1,2-Cyclohexanedicarboxylic acid is

b) The structure of heptanoic acid is ${\mathbf{HO}}_{\mathbf{2}}{\mathbf{CCH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CO}}_{\mathbf{2}}\mathbf{H}$

c) The structure of 2-Hexen-4-ynoic acid${\mathbf{CH}}_{\mathbf{3}}\mathbf{C}\equiv \mathbf{CCH}\mathbf{=}{\mathbf{CHCO}}_{\mathbf{2}}\mathbf{H}$

d) The structure of 4-Ethyl-2-propyloctanoic acid is

e)  The structure of 3-chlorophthalic acid is

f) The structure of triphenylacetic acid is ${\left({\mathbf{C}}_{\mathbf{6}}{\mathbf{H}}_{\mathbf{5}}\right)}_{\mathbf{3}}{\mathbf{CCO}}_{\mathbf{2}}\mathbf{H}$

g) The structure of 2-Cyclobutenecarbonitrile is

h)  The structure of m-Benzoylbenzonitrile is

Step 1: Definition of structure

The arrangement of chemical bonds between atoms in a molecule is defined as structure.

Step 2: Structure of the IUPAC name

a) The compound has a cyclohexane ring with two carboxylic acid groups in 1,2 position arranged in the same side of the ring.

The structure of cis-1,2-Cyclohexanedicarboxylic acid is

b) The compound has a seven carbon straight chain with two carboxyl groups at the ends.

The structure of heptanedioic acid is ${\mathbf{HO}}_{\mathbf{2}}{\mathbf{CCH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CO}}_{\mathbf{2}}\mathbf{H}$

c) The compound has a six-carbon straight chain with a carboxylic group, a double bond between$C_2\&C_3$ and a triple bond between$C_4\&C_5$

The structure of 2-Hexen-4-ynoic acid ${\mathbf{CH}}_{\mathbf{3}}\mathbf{C}\equiv \mathbf{CCH}\mathbf{=}{\mathbf{CHCO}}_{\mathbf{2}}\mathbf{H}$

d) The compound is an octane derivative and has a carboxyl group, a propyl group $c_2$on  and an ethyl group on$c_4$

The structure of 4-Ethyl-2-propyloctanoic acid is

e) The compound is a benzene derivative with two carboxyl groups on $c_1\&c_2$$c_1\&c_2$and a chlorine atom on$c_3$

The structure of 3-chlorophthalic acid is

f) The name of the compound shows that it has three phenyl groups instead of the three hydrogen atoms present in the methyl group in acetic acid.

The structure of triphenylacetic acid is ${\left({\mathbf{C}}_{\mathbf{6}}{\mathbf{H}}_{\mathbf{5}}\right)}_{\mathbf{3}}{\mathbf{CCO}}_{\mathbf{2}}\mathbf{H}$

g) The compound has a nitrile group attached to a cyclobutene ring with a double bond between $c_{2 }\& c_3$

The structure of 2-Cyclobutenecarbonitrile is

h) The compound has a benzene ring attached to a nitrile group and a benzoyl group with a meta relationship.

The structure of m-Benzoylbenzonitrile is