Chapter 21.SE, Problem 46AP

Interpretation Introduction

a) p-Bromo phenyl acetamide.

Interpretation:

To draw the structural formula from the given name. We retrace steps as in the IUPAC system.

Answer to Problem 46AP

Explanation of Solution

To derive the structure corresponding to the given IUPAC name, we need to take recourse to the IUPAC system, but somewhat retracing the steps. Thus:

1) The given name p-Bromo phenyl acetamide than the suffix –amide.

At the very outset, Thus, the compound is invariably an amide.

2) The general formula for an amide is

3) Identify now the alkyl group R attached to the carbonyl carbon. This, for the given name p-Bromo phenyl aceta is

The phenyl ring with a Bromine for at the pare position curt the intervening –CH₂. That is

4) Recall the parent acetic acid is a 2-carbon acid system

It the given compound the phenyl ring is at C₂ ie

It is a substituted acetic acid. Hence the aceta naming

Combining these aspects, it follows that the parent carboxylic acid is acetic acid, substituted by the p-bromo phenyl at one H is by

Thus the structure of the given compound where name is p-bromo phenyl acetamide is

Is further substituted

Conclusion

Thus the structure corresponding to the given name p-bromo phenyl acetamide is

Interpretation Introduction

b) m-Benzoylbenzamide

Interpretation:

To draw the structural formula from the given name. We retrace steps as in the IUPAC system.

Answer to Problem 46AP

Explanation of Solution

The structure corresponding to the given name can be obtained by taking recourse to the IUPAC system, in a reverse way: Thus

1) First, the name ends with –amide as suffix. Thus, the compound is an amide and its general formula may be written

2) Now, identify the R ie alkyl group attached to the carbonyl carbon.

[Also, it must be noted that the amide is not substituted at nitrogen as the name has no N-alkyl prefix] the R is m-benzoyl benzoyl implying for Benzamide with a further benzoyl, at the meta carbon, C-3 of the phenyl ring.

Thus,

or

Thus the structure of the compounds as

Conclusion

Thus the compound with the given IUPAC name m-benzoyl benzamide has the structure

Interpretation Introduction

c) 2,2-Dimethyl hexanamide

Interpretation:

To draw the structural formula from the given name. We retrace steps as in the IUPAC system.

Answer to Problem 46AP

Explanation of Solution

The structure corresponding to the given IUPAC mane 2,2-Dimethylhexanamide can be obtained by retracing the steps of the IUPAC system. Thus,

a) First, observe that the given, IUPAC name has the suffix–amide.

Thus the compound is an amide.

b) The name has no alkyl substituent at the nitrogen of the amino –NH₂ group. So the compound should have a structure consistent with the general formula

c) Now to identify the R-alkyl portion, we see it is 2,2-Dimethyl hexane chain, ie

By convention, the carbonyl carbon is C-1, C-2 has 2 methyl groups. Thus the parent (longest) hydrocarbon chain –R is 2,2-dimethylhexane.

Thus the structure should be

Conclusion

Thus the structure corresponding to the compound whose IUPAC name is 2,2-dimethyl hexanamide is

Interpretation Introduction

d) Cyclohexyl cyclohexane carboxylate

Interpretation:

To draw the structural formula from the given name. We retrace steps as in the IUPAC system.

Answer to Problem 46AP

Explanation of Solution

The structure of the compound with the given IUPAC name

Cyclohexyl cyclohexane carboxylate can be obtained by retracing the rules of the IUPAC system: Thus.

1) First the, given name has its suffix: carboxylate

Thus it is an ester of a carboxylic acid.

2) Second, recall that the alkyl R¹ of the ester oxygen comes first in the IUPAC name. In the given name this R¹ is cyclohexyl. Thus the OR¹ of the ester (general)

Is cyclohexyl structure is

3) For the R (alkyl) component attached to the carbonyl carbon, it is given as cyclohexane. This implies the structure

By convention, the cyclohexane carboxylic acid ester is named by replacing the carboxylic acid ending by carboxylate. Assembling all these rules, the structure of the compound corresponding to the name cyclohexyl cyclohexane carboxylate is

Conclusion

Thus the structure of the compound that best fits the given IUPAC name is

Interpretation Introduction

e) Ethyl-2-cyclobutene carboxylate

Interpretation:

To draw the structural formula from the given name. We retrace steps as in the IUPAC system.

Answer to Problem 46AP

Explanation of Solution

The structure of the compound whose IUPAC name is Ethyl 2-cyclobutene carboxyl may be obtained by retracing the rules of the IUPAC system. Thus,

1) First, we see that the suffix of the name is carboxylate.

Thus the compound is an ester.

2) Second, the general formula of the ester may be written

3) Third, by convention, the ester alkyl function R¹ comes as prefix in the IUPAC name for the given compound it is ethyl –CH₂CH₃. Thus, the compound could be

4) Next we identify that the alkyl component R of the carbonyl carbon from the name is 2-cyclobutene ie

With the double bond at C-2; since C-1 of the cyclobutene ring must by convention carry the carboxylic carbon of the acyl group

Finally the ester ending is carboxylate which agrees with the facts-is the compound is an ester of a cyclohexyl carboxylic acid

Thus the compound is an ester.

Conclusion

Thus the structure of the compound where IUPAC name is ethyl 2-cyclobutene carboxylate is

Interpretation Introduction

f) Succinic anhydride

Interpretation:

To draw the structural formula from the given name. We retrace steps as in the IUPAC system.

Answer to Problem 46AP

Explanation of Solution

The structured formula of the compound corresponding to the given name succinic an hydride is obtained by retracing the rules of the IUPAC system. Thus,

1) First, the given name has its suffix anhydride. The compound is thus, an anhydride of a carboxylic acid.

2) The general formula for an acid anhydride of a mono carboxylic acid as

Where R and R¹ are the two alkyl groups may be similar R=R in which care it is a synmetical an hydride, or R≠R¹, for an unsynmetical an hydride. It is now needed to identify R and R¹.

Now for this, we introspect the prefix of the name is succinic this implies the parent acid is a dicarboxylic acid is succinic acid. Its formula is

Since by reaction and convention, acid an hydride form by lon of a water molecule, thus,

Thus consistent with the above facts the structural formula for succinic an hydride is

Conclusion

Thus the structural formula for succinic anhydride is