Question

Draw a structural formula for each compound. (a) Dimethyl carbonate (b) Benzonitrile (c) Isopropyl 3-methylhexanoate (d) Diethyl oxalate (e) Ethyl (Z)-2-pentenoate (f) Butanoic anhydride (g) Dodecanamide (h) Ethyl 3-hydroxybutanoate (i) Octanoyl chloride (j) Diethyl cis-1,2-cyclohexanedicarboxylate (k) Methanesulfonyl chloride (1) \(p\)-Toluenesulfonyl chloride

Short answer

Based on the given step-by-step solution, provide a short answer for each of the following structural formulas: a) Dimethyl carbonate: O=C(OC)2. b) Benzonitrile: C6H5CN. c) Isopropyl 3-methylhexanoate: (CH3)2CHOOC(CH3)CH2CH(CH3)CH2CH2CH3. d) Diethyl oxalate: CH3CH2OOC-CO-OCH2CH3. e) Ethyl (Z)-2-pentenoate: CH3CH=CHCH2COOCH2CH3. f) Butanoic anhydride: (CH3CH2CH2CO)2O. g) Dodecanamide: CH3(CH2)10CONH2. h) Ethyl 3-hydroxybutanoate: CH3CH(OH)CH2COOCH2CH3. i) Octanoyl chloride: CH3(CH2)6COCl. j) Diethyl cis-1,2-cyclohexanedicarboxylate: CH3CH2OOC-C1H(C2H)COOCH2CH3 (C1 and C2 are adjacent carbons of the cyclohexane ring in a cis configuration). k) Methanesulfonyl chloride: CH3SO2Cl. (1) p-Toluenesulfonyl chloride: CH3C6H4SO2Cl.

Step-by-step solution

a) Dimethyl carbonate

The name tells us that it is a carbonate ester with two methyl groups. The central atom is carbon, which is attached to three oxygen atoms. Two of the oxygen atoms are bonded to a methyl group, and the third has a double bond with the carbon atom. The structural formula is: O=C(OC)2.

b) Benzonitrile

The name suggests that the nitrile functional group is attached to a benzene ring. A nitrile functional group consists of a carbon atom triple-bonded to a nitrogen atom. Draw a benzene ring and attach the nitrile group to one of the carbons. The structural formula is: C6H5CN.

c) Isopropyl 3-methylhexanoate

This ester consists of a 3-methylhexanoate group and an isopropyl group. The carboxylate part of the ester has a 3-methylhexane chain, and the alcohol part has an isopropyl group. The structural formula is: (CH3)2CHOOC(CH3)CH2CH(CH3)CH2CH2CH3.

d) Diethyl oxalate

This is an ester derived from oxalic acid and ethanol. Oxalic acid has two carbonyl groups, and both are esterified by ethyl groups. The structural formula is: CH3CH2OOC-CO-OCH2CH3.

e) Ethyl (Z)-2-pentenoate

The name tells us that we have an ethyl ester of a (Z)-2-pentenoic acid. Draw a 5-carbon chain with a double bond between the second and the third carbon, and ethyl ester at the end of the chain. The structural formula is: CH3CH=CHCH2COOCH2CH3.

f) Butanoic anhydride

An anhydride group consists of two carbonyl groups connected by an oxygen atom. Butanoic anhydride has two butanoic acid residues. The structural formula is: (CH3CH2CH2CO)2O.

g) Dodecanamide

A dodecanamide consists of a 12-carbon chain with an amide functional group at one end. The amide group consists of a carbonyl group and a nitrogen atom. The structural formula is: CH3(CH2)10CONH2.

h) Ethyl 3-hydroxybutanoate

Ethyl 3-hydroxybutanoate is an ester made from 3-hydroxybutanoic acid and ethanol. In this molecule, the hydroxyl group is on the third carbon of the chain. The structural formula is: CH3CH(OH)CH2COOCH2CH3.

i) Octanoyl chloride

This is an acyl chloride of an 8-carbon chain. The functional group is a carbonyl group with a chlorine atom attached. The structural formula is: CH3(CH2)6COCl.

j) Diethyl cis-1,2-cyclohexanedicarboxylate

A cis-1,2-cyclohexanedicarboxylate has two carboxylate groups in the cis configuration on carbons 1 and 2 of the cyclohexane ring. Diethyl tells us that both carboxylate groups are esterified with ethyl groups. The structural formula is: CH3CH2OOC-C1H(C2H)COOCH2CH3, where C1 and C2 are adjacent carbons of the cyclohexane ring in a cis configuration.

k) Methanesulfonyl chloride

Methanesulfonyl chloride is a sulfonyl chloride with a single carbon atom. The sulfonyl chloride functional group has a sulfur atom double-bonded to an oxygen atom and single-bonded to a chlorine atom and a carbon atom. The structural formula is: CH3SO2Cl.

(1) p-Toluenesulfonyl chloride

p-Toluenesulfonyl chloride has a toluene group connected to a sulfonyl chloride functional group at the para position. Toluene is a benzene ring with a methyl group attached. The structural formula is: CH3C6H4SO2Cl.