Chapter 8, Problem 8.5P

Interpretation Introduction

(a)

Interpretation:

The substitutive name for the given compound is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

Answer to Problem 8.5P

The substitutive name for the given compound is $\text{1-butanol}$.

Explanation of Solution

The given compound is ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}$. It consists of a chain of four carbon atoms with hydroxyl group attached at the first carbon atom. The alcohols contain hydroxyl $\left(\text{OH}\right)$ functional group in their parent chain and are named by adding suffix –ol. Therefore, the name of this compound is $\text{1-butanol}$.

Conclusion

The substitutive name for the given compound is $\text{1-butanol}$.

Interpretation Introduction

(b)

Interpretation:

The substitutive name for the given compound is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

Answer to Problem 8.5P

The substitutive name for the given compound is $\text{3-bromo-1-butanol}$.

Explanation of Solution

The given compound is ${\text{CH}}_{\text{3}}{\text{CHBrCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}$. It consists of a chain of four carbon atoms with hydroxyl group attached at the first carbon atom. The alcohols contain hydroxyl $\left(\text{OH}\right)$ functional group in their parent chain and are named by adding suffix –ol. The bromo group is attached at the third carbon atom. Therefore, the name of this compound is $\text{3-bromo-1-butanol}$.

Conclusion

The substitutive name for the given compound is $\text{3-bromo-1-butanol}$.

Interpretation Introduction

(c)

Interpretation:

The substitutive name for the given compound is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

Answer to Problem 8.5P

The substitutive name for the given compound is $\text{(}E\text{)-1-chloro-3-methyl-3-pentene-2-ol}$.

Explanation of Solution

The given compound is shown below.

Figure 1

The given compound has a longest chain of five carbon atoms with a double bond on third carbon atom. It is an alkene, the suffix used for an alkene is –ene. Therefore, the parent name is pentene. One chloro group is attached at the first carbon atom, one methyl group is attached at the third carbon atom and one hydroxyl group is attached at the second carbon atom.

The use of prefix $E$ and $Z$ depends upon the location of the higher priority groups. When the priority groups located on the opposite side then it is an $E$ isomer, whereas when two higher priority groups located on the same side then it is an $Z$ isomer. The priority order depends upon the atomic number of the elements. Therefore, the name of this compound is $\text{(}E\text{)-1-chloro-3-methyl-3-pentene-2-ol}$.

Conclusion

The substitutive name for the given compound is $\text{(}E\text{)-1-chloro-3-methyl-3-pentene-2-ol}$.

Interpretation Introduction

(d)

Interpretation:

The substitutive name for the given compound is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

Answer to Problem 8.5P

The substitutive name for the given compound is $\left(1S,5R\right)\text{-2-chloro-5-methylcyclopent-2-enethiol}$.

Explanation of Solution

The given compound is shown below.

Figure 2

The given compound has a cyclic ring of five carbon atoms with a double bond on second carbon atom. It is an alkene, the suffix used for an alkene is –ene. Therefore, the parent name is $\text{cyclopent-2-ene}$. One chloro group is attached at the second carbon atom, one methyl group is attached at the fifth carbon atom and one thiol group is attached at the first carbon atom.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other. Therefore, the name of this compound is $\left(1S,5R\right)\text{-2-chloro-5-methylcyclopent-2-enethiol}$.

Conclusion

The substitutive name for the given compound is $\left(1S,5R\right)\text{-2-chloro-5-methylcyclopent-2-enethiol}$.

Interpretation Introduction

(e)

Interpretation:

The substitutive name for the given compound is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

Answer to Problem 8.5P

The substitutive name for the given compound is $\left(2R,3R,4S\right)\text{-3-butylhex-5-ene-2, 4-diol}$.

Explanation of Solution

The given compound is shown below.

Figure 3

The given compound has a chain of six carbon atoms with a double bond on fifth carbon atom. It is an alkene, the suffix used for an alkene is –ene. Therefore, the parent name is $\text{hex-5-ene}$. One butyl group is attached at the third carbon atom and two hydroxyl groups are attached at the second and fourth carbon atoms.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other. Therefore, the name of this compound is $\left(2R,3R,4S\right)\text{-3-butylhex-5-ene-2, 4-diol}$.

Conclusion

The substitutive name for the given compound is $\left(2R,3R,4S\right)\text{-3-butylhex-5-ene-2, 4-diol}$.

Interpretation Introduction

(f)

Interpretation:

The substitutive name for the given compound is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

Answer to Problem 8.5P

The substitutive name for the given compound is $\text{cyclohexa-2, 5-diene-1-ol}$.

Explanation of Solution

The given compound is shown below.

Figure 4

It consists of a cyclic ring of six carbon atoms. Therefore, the parent name is cyclohexa. There are two double bonds present at the second and fifth carbon atom of the ring. Also, one hydroxyl group is attached at the first carbon atom. Therefore, the name of this compound is $\text{cyclohexa-2, 5-diene-1-ol}$.

Conclusion

The substitutive name for the given compound is $\text{cyclohexa-2, 5-diene-1-ol}$.

Interpretation Introduction

(g)

Interpretation:

The substitutive name for the given compound is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

Answer to Problem 8.5P

The substitutive name for the given compound is $\text{1-mercaptopentan-2-ol}$.

Explanation of Solution

The given compound is shown below.

Figure 5

It consists of a chain of five carbon atoms with hydroxyl group attached at the second carbon atom. The alcohols contain hydroxyl $\left(\text{OH}\right)$ functional group in their parent chain and are named by adding suffix –ol. The –SH group is attached at the first carbon atom. Therefore, the name of this compound is $\text{1-mercaptopentan-2-ol}$.

Conclusion

The substitutive name for the given compound is $\text{1-mercaptopentan-2-ol}$.

Interpretation Introduction

(h)

Interpretation:

The substitutive name for the given compound is to be stated.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order.

Answer to Problem 8.5P

The substitutive name for the given compound is $\text{2-methylpropan-2-thiol}$.

Explanation of Solution

The given compound is shown below.

Figure 6

It consists of a chain of three carbon atoms with thiol group attached at the second carbon atom. One methyl group is attached at the second carbon atom. Therefore, the name of this compound is $\text{2-methylpropan-2-thiol}$.

Conclusion

The substitutive name for the given compound is $\text{2-methylpropan-2-thiol}$.