Q46E - Organic Chemistry (Mcmurry)

Question

21-46 Draw structures corresponding to the following names

1. p-Bromophenylacetamide
2. m-Benzoylbenzamide
3. 2,2-Dimethylhexanamide
4. Cyclohexyl cyclohexanecarboxylate
5. Ethyl 2-cyclobutenecarboxylate
6. Succinic anhydride

Step-by-Step Solution

Answer

a. The structure of p-Bromophenylacetamide is 

b. The structure of m-Benzoylbenzamide is 

c. The structure of 2,2-Dimethylhexanamide is 

d. The structure of Cyclohexyl cyclohexane carboxylate is 

e. The structure of Ethyl 2-cyclobutenecarboxylate is 

f. The structure of Succinic anhydride is  

Step 1: Introduction to the Concept

A chemical compound's structural formula is a graphic depiction of the molecular structure (derived by structural chemistry methods) that shows how the atoms might be organised in real three-dimensional space.

Step 2: Determination of the structure of p-Bromophenylacetamide

a)

We must use the IUPAC system to determine the structure matching to the supplied IUPAC name, however, we must partly retrace our steps. Thus:

1) The suffix-amide is more common than the given name p-Bromo phenyl acetamide.

As a result, the compound is invariably an amide from the start.

2) An amide's general formula is 

$\mathrm{R}-\stackrel{\mathrm{O}}{\stackrel{\parallel }{\mathrm{C}}}-{\mathrm{NH}}_2$

3) Now you must identify the alkyl group R that is connected to the carbonyl carbon. This is the chemical compound p-Bromo phenyl aceta.

At the pare position, the phenyl ring with a bromine curt the intervening  $-{\mathrm{CH}}_2$. That

4) Keep in mind that acetic acid is a two-carbon acid system.

If the phenyl ring is at ${\mathrm{C}}_2$  in the given molecule,

It's acetic acid that's been substituted. As a result, the word aceta was coined.

Based on these considerations, the parent carboxylic acid is acetic acid.

The p-bromo phenyl is  replaced at one H

by

As a result, the structure of the provided molecule, p-bromo phenyl acetamide, is

Step 3: Determination of structure of m-Benzoylbenzamide

b)

Using the IUPAC approach in the other direction, the structure matching to the given name can be found: Thus

1. The suffix -amide is used at the end of the name. As a result, the chemical is an amide, and its general formula,

   $\mathrm{R}-\stackrel{\mathrm{O}}{\stackrel{\parallel }{\mathrm{C}}}-\underset{\mathrm{amide}}{{\mathrm{NH}}_2}$
   

   
   

   
   

2. Next, locate the R i.e., alkyl group on the carbonyl carbon.

   
   

   
   

[It's also worth noting that the amide isn't replaced at nitrogen because the name has 

prefix rather than a N-alkyl prefix.] The R stands for m-benzoyl benzoyl, meaning that Benzamide has another benzoyl at the meta carbon, C-3 of the phenyl ring.

Thus,

Or

Therefore the structure is 

Step 4: Determination of structure of 2,2-Dimethylhexanamide

c)

By repeating the stages of the IUPAC system, the structure corresponding to the given IUPAC name 2,2-Dimethylhexanamide can be found. As a result, 

a) first, note that the IUPAC name bears the suffix-amide.

As a result, the chemical is classified as an amide.

b) There is no alkyl substituent at the amino $-{\mathrm{NH}}_2$ group's nitrogen. As a result, the structure of the chemical should be consistent with the general formula.

$\mathrm{R}-\stackrel{\mathrm{O}}{\stackrel{\parallel }{\mathrm{C}}}-{\mathrm{NH}}_2$

c) To identify the R-alkyl part, we can observe that it is a 2,2-Dimethyl hexane chain, i.e.

 

the carbonyl carbon is C-1, and C-2 contains two methyl groups by convention. As a result, 2,2 dimethylhexane is the parent (longest) hydrocarbon chain -R.

As a result, the framework should be

Therefore, the structure of 2,2-Dimethylhexanamide is 

Step 5: Determination of structure of Cyclohexyl cyclohexanecarboxylate

d)

By retracing the rules of the IUPAC system, the structure of the compound with the given IUPAC name Cyclohexyl cyclohexane carboxylate may be determined: Thus.

1) To begin, the given name has a suffix: carboxylate

As a result, it is a carboxylic acid ester.

2) Second, keep in mind that the ester oxygen's alkyl   is listed first in the IUPAC nomenclature. This ${\mathbf{R}}^{\mathbf{1}}$ is cyclohexyl in the given name. As a result, the ester's ${\mathbf{OR}}^{\mathbf{1}}$  (general)

Here the cyclohexyl structure

3. For the R (alkyl) component connected to the carbonyl atom. This means that the structure exists.

The carboxylic acid end of the cyclohexane carboxylic acid ester is replaced with carboxylate by convention. By combining all of these principles, the structure of the chemical known as cyclohexyl cyclohexane carboxylate may be determined.

Therefore the structure of Cyclohexyl cyclohexane carboxylate is 

Step 6: Determination of structure of Ethyl 2-cyclobutenecarboxylate

e)

The structure of the molecule Ethyl 2 cyclobutene carboxyl, which is the IUPAC name, may be determined by retracing the IUPAC rules. As a result, 

1. we can see that the name's suffix is carboxylate.

    As a result, the chemical is classified as an ester.

2.The ester's general formula can be written in two ways.

3.Finally, the ester alkyl function ${\mathbf{R}}^{\mathbf{1}}$  is used as a prefix in the IUPAC nomenclature for the provided compound, which is ${\mathbf{\text{ethyl -CH}}}_{\mathbf{\text{2}}}{\mathbf{\text{CH}}}_{\mathbf{\text{3}}}$ . As a result, the compound may be

4. From the nomenclature, we can deduce that the alkyl component R of the carbonyl carbon is 2-cyclobutene.

Due to the double bond at C-2, the carboxylic carbon of the acyl group must be carried by convention on C-1 of the cyclobutene ring.

$\mathrm{R}-\stackrel{\mathrm{O}}{\stackrel{\parallel }{\mathrm{C}}}-$

Finally, the carboxylate end of the ester agrees with the facts, namely that the molecule is an ester of a cyclohexyl carboxylic acid.

As a result, the chemical is classified as an ester.

Step 7: Determination of structure of Succinic anhydride

f)

Retracing the rules of the IUPAC system yields the structural formula of the compound with the given name succinic a hydride. As a result, 

1) The given name has the suffix anhydride. As a result, the chemical is a carboxylic acid anhydride.

2) The general formula for a mono carboxylic acid's acid anhydride is

Where R and ${\mathbf{R}}^{\mathbf{1}}$  are two alkyl groups, they can be comparable  $\mathbf{\text{R=R}}$, indicating a synmetical hydride, or $\mathbf{\text{R}}\mathbf{\ne }{\mathbf{\text{R}}}^{\mathbf{\text{1}}}$, indicating an unsynmetical hydride. R and  ${\mathbf{R}}^{\mathbf{1}}$ must now be distinguished.

Now, we'll look at the name's prefix, which is succinic. This indicates that the parent acid is succinic acid, which is a dicarboxylic acid. Its formula is as follows:

Because acid and hydride produced by the lon of a water molecule through reaction and convention,

In light of the foregoing, the structural formula for succinic anhydride is