Chapter 22, Problem 22.5P

Draw the structure corresponding to each name.

a. $\text{5-methylheptanoylchloride}$

b. isopropyl propanoate

c. acetic formic anhydride

d. N-isobutyl-N-methylbutanamide

e. $\text{3-methylpentanenitrile}$

f. o-cyanobenzoic acid

g. $sec\text{-butyl}\text{2-methylhexanoate}$

h. N-ethylhexanamide

Interpretation Introduction

(a)

Interpretation: The structure corresponding to the given name is to be drawn.

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.5P

The structure corresponding to the given name is,

Explanation of Solution

The given name indicates that compound contains acid chloride (name ends with –yl chloride) as the functional group and heptane as the longest carbon chain with one methyl substitution at $\text{C5}$ position. Thus, the structure of $\text{5-methylheptanoylchloride}$ is drawn as follows.

Figure 1

Conclusion

The structure corresponding to the given name is drawn in Figure 1.

Interpretation Introduction

(b)

Interpretation: The structure corresponding to the given name is to be drawn.

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.5P

The structure corresponding to the given name is,

Explanation of Solution

The given name indicates that compound contains ester (name ends with –ate) as the functional group and propane as the longest carbon chain with one isopropyl substitution as $-\text{OR}$.

Thus, the structure of isopropyl propanoate is drawn as follows.

Figure 2

Conclusion

The structure corresponding to the given name is drawn in Figure 2.

Interpretation Introduction

(c)

Interpretation: The structure corresponding to the given name is to be drawn.

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.5P

The structure corresponding to the given name is,

Explanation of Solution

The given name indicates that compound contains anhydride (name ends with -anhydride) as the functional group, which is derived from acetic acid and formic acid. Thus, it is a mixed anhydride. The structures of mixed anhydrides are drawn by joining the one ends of $\text{C}=\text{O}$ bonds of acids to $\text{O}$ atom.

Hence, the structure of acetic formic anhydride is drawn as follows.

Figure 3

Conclusion

The structure corresponding to the given name is drawn in Figure 3.

Interpretation Introduction

(d)

Interpretation: The structure corresponding to the given name is to be drawn.

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.5P

The structure corresponding to the given name is,

Explanation of Solution

The given name indicates that compound contains amide (name ends with -amide) as the functional group and butane as the longest carbon chain with one methyl and one isobutyl substitutions at $\text{N}$ atom. Therefore, the structure of N-isobutyl-N-methylbutanamide is drawn as follows.

Figure 4

Conclusion

The structure corresponding to the given name is drawn in Figure 4.

Interpretation Introduction

(e)

Interpretation: The structure corresponding to the given name is to be drawn.

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.5P

The structure corresponding to the given name is,

Explanation of Solution

The given name indicates that compound contains cyano (name ends with –nitrile) as the functional group and pentane as the longest carbon chain with one methyl substitution at $\text{C3}$ position. Therefore, the structure of $\text{3-methylpentanenitrile}$ is drawn as follows.

Figure 5

Conclusion

The structure corresponding to the given name is drawn in Figure 5.

Interpretation Introduction

(f)

Interpretation: The structure corresponding to the given name is to be drawn.

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.5P

The structure corresponding to the given name is,

Explanation of Solution

The given name indicates that compound contains carboxylic acid (name ends with -oic acid) as the functional group, which is attached to the benzene ring with one cyano group at ortho position. Therefore, the structure of o-cyanobenzoic acid is drawn as follows.

Figure 6

Conclusion

The structure corresponding to the given name is drawn in Figure 6.

Interpretation Introduction

(g)

Interpretation: The structure corresponding to the given name is to be drawn.

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.5P

The structure corresponding to the given name is,

Explanation of Solution

The given name indicates that compound contains ester (name ends with –ate) as the functional group and hexane as the longest carbon chain with one methyl substitution at $\text{C2}$ and one secondary butyl group as $-\text{OR}$. Therefore, the structure of sec-butyl $2$-methlhexanoate is drawn as follows.

Figure 7

Conclusion

The structure corresponding to the given name is drawn in Figure 7.

Interpretation Introduction

(h)

Interpretation: The structure corresponding to the given name is to be drawn.

Concept introduction: One should follow the given steps to draw the structure of a compound from its name. The first step is identification of parent name and functional group found at the end of the name. The second step is numbering of carbon skeleton in the direction, where functional group gets a lower number. The third step is addition of substituents at appropriate atoms.

Answer to Problem 22.5P

The structure corresponding to the given name is,

Explanation of Solution

The given name indicates that compound contains amide (name ends with -amide) as the functional group and hexane is the longest carbon chain with one ethyl substitution to $\text{N}$ atom.

Therefore, the structure of N-ethylhexanamide is drawn as follows.

Figure 8

Conclusion

The structure corresponding to the given name is drawn in Figure 8.