Chapter 13, Problem 26PP

(a)

Interpretation Introduction

Interpretation: For the given set of molecules the IUPAC name to be predicted.

Concept Introduction:

1. 1. IUPAC rules for naming ethers.
   1. i. Choose the larger group to be the parent alkane and naming the smaller group as an alkoxy substituent. Systematic names must be used for the complex ethers that exhibit multiple substituents and/or chirality centers.
2. 2. IUPAC rules for naming thiols.
   1. ii. The nomenclature of thiol is similar to alcohol; thiol has $\text{SH}$ instead of $\text{OH}$ whereas the suffix of the name is ‘thiol’ instead of ‘ol’. If the compound containing other functional group then the $\text{SH}$ group is named as ‘mercapto’ in the prefix (substituent).
3. 3. IUPAC rules for naming sulfides.
   1. iii. Naming is similar to ether; common name with the suffix as ‘sulfide’. If the compound has other functional group then ‘alkylthio’ is added as the substituent in the prefix.
4. 4. IUPAC rules for naming sulfoxide.
   1. iv. Naming is similar to sulfide; common name with the suffix as ‘sulfoxide’.

Answer to Problem 26PP

IUPAC name is $\text{(1S,2S)-1-Ethoxy-2-methylcyclohexane}$

Explanation of Solution

Predict the IUPAC nomenclature.

The IUPAC name must contain all the information regarding the structure of the compound. The structure of the ether contain two chiral centers (predict the configuration of two chiral centers and include in the beginning of the name). The structure is categorized into larger (cyclohexane) and smaller group (alkoxy substituent- ethoxy). The position of the methyl substituent in the larger group is accounted by numbering the larger group.

Here the larger group (cyclohexane) to be the parent alkane and the smaller group (ethoxy) as an alkoxy substituent. Finally, IUPAC name is $\text{(1S,2S)-1-Ethoxy-2-methylcyclohexane}$.

(b)

Interpretation Introduction

Interpretation: For the given set of molecules the IUPAC name to be predicted.

Concept Introduction:

1. 5. IUPAC rules for naming ethers.
   1. v. Choose the larger group to be the parent alkane and naming the smaller group as an alkoxy substituent. Systematic names must be used for the complex ethers that exhibit multiple substituents and/or chirality centers.
2. 6. IUPAC rules for naming thiols.
   1. vi. The nomenclature of thiol is similar to alcohol; thiol has $\text{SH}$ instead of $\text{OH}$ whereas the suffix of the name is ‘thiol’ instead of ‘ol’. If the compound containing other functional group then the $\text{SH}$ group is named as ‘mercapto’ in the prefix (substituent).
3. 7. IUPAC rules for naming sulfides.
   1. vii. Naming is similar to ether; common name with the suffix as ‘sulfide’. If the compound has other functional group then ‘alkylthio’ is added as the substituent in the prefix.
4. 8. IUPAC rules for naming sulfoxide.
   1. viii. Naming is similar to sulfide; common name with the suffix as ‘sulfoxide’.

Answer to Problem 26PP

 IUPAC name is $\text{(1R)-2-Ethoxybutane}$

Explanation of Solution

Predict the IUPAC nomenclature.

The IUPAC name must contain all the details regarding the structure of the compound (including position of substituents, configuration of chiral center and double bond). The structure of the ether contain one chiral center (predict the configuration of chiral center and include at the beginning of name). The structure is categorized into larger (butane) and smaller group (alkoxy- ethoxy). The position of the small group on the parent chain (alkane) is accounted by numbering the parent chain.

Here the larger group (butane) to be the parent alkane and the smaller group (ethoxy) as an alkoxy substituent is located at $\text{position-2}$. Finally, IUPAC name is $\text{(1R)-2-Ethoxybutane}$.

(c)

Interpretation Introduction

Interpretation: For the given set of molecules the IUPAC name to be predicted.

Concept Introduction:

1. 9. IUPAC rules for naming ethers.
   1. ix. Choose the larger group to be the parent alkane and naming the smaller group as an alkoxy substituent. Systematic names must be used for the complex ethers that exhibit multiple substituents and/or chirality centers.
2. 10. IUPAC rules for naming thiols.
   1. x. The nomenclature of thiol is similar to alcohol; thiol has $\text{SH}$ instead of $\text{OH}$ whereas the suffix of the name is ‘thiol’ instead of ‘ol’. If the compound containing other functional group then the $\text{SH}$ group is named as ‘mercapto’ in the prefix (substituent).
3. 11. IUPAC rules for naming sulfides.
   1. xi. Naming is similar to ether; common name with the suffix as ‘sulfide’. If the compound has other functional group then ‘alkylthio’ is added as the substituent in the prefix.
4. 12. IUPAC rules for naming sulfoxide.
   1. xii. Naming is similar to sulfide; common name with the suffix as ‘sulfoxide’.

Answer to Problem 26PP

 IUPAC name is $\text{(S)-3- Hexanethiol}$

Explanation of Solution

Predict the IUPAC nomenclature.

The IUPAC name must contain all the details regarding the structure of the compound (including position of substituents, configuration of chiral center and double bond). The structure of the thiol contain one chiral center (predict the configuration of chiral center and include at the beginning of name). The structure is categorized into parent chain and substituent (thiol) group. The position of the thiol on the parent chain (alkane) is accounted by numbering the parent chain.

Here the hexane to be the parent alkane and the smaller group (thiol) as substituent is located at $\text{position-3}$. Finally, IUPAC name is $\text{(S)-3- Hexanethiol}$.

(d)

Interpretation Introduction

Interpretation: For the given set of molecules the IUPAC name to be predicted.

Concept Introduction:

1. 13. IUPAC rules for naming ethers.
   1. xiii. Choose the larger group to be the parent alkane and naming the smaller group as an alkoxy substituent. Systematic names must be used for the complex ethers that exhibit multiple substituents and/or chirality centers.
2. 14. IUPAC rules for naming thiols.
   1. xiv. The nomenclature of thiol is similar to alcohol; thiol has $\text{SH}$ instead of $\text{OH}$ whereas the suffix of the name is ‘thiol’ instead of ‘ol’. If the compound containing other functional group then the $\text{SH}$ group is named as ‘mercapto’ in the prefix (substituent).
3. 15. IUPAC rules for naming sulfides.
   1. xv. Naming is similar to ether; common name with the suffix as ‘sulfide’. If the compound has other functional group then ‘alkylthio’ is added as the substituent in the prefix.
4. 16. IUPAC rules for naming sulfoxide.
   1. xvi. Naming is similar to sulfide; common name with the suffix as ‘sulfoxide’.

Answer to Problem 26PP

 IUPAC name is $\text{Ethyl}\text{propyl}\text{sulfoxide}$

Explanation of Solution

Predict the IUPAC nomenclature.

The IUPAC name must contain all the details regarding the structure of the compound (including position of substituents, configuration of chiral center and double bond). The nomenclature of the sulfoxide is similar to sulfide. In the nomenclature of the sulfoxide which the structure is categorized into two substituents one is propyl and other is ethyl group. Nomenclature should contain both substituents arranged in the alphabetical order followed by the suffix ‘sulfoxide’.

Finally, IUPAC name is $\text{Ethyl}\text{propyl}\text{sulfoxide}$.

(e)

Interpretation Introduction

Interpretation: For the given set of molecules the IUPAC name to be predicted.

Concept Introduction:

1. 17. IUPAC rules for naming ethers.
   1. xvii. Choose the larger group to be the parent alkane and naming the smaller group as an alkoxy substituent. Systematic names must be used for the complex ethers that exhibit multiple substituents and/or chirality centers.
2. 18. IUPAC rules for naming thiols.
   1. xviii. The nomenclature of thiol is similar to alcohol; thiol has $\text{SH}$ instead of $\text{OH}$ whereas the suffix of the name is ‘thiol’ instead of ‘ol’. If the compound containing other functional group then the $\text{SH}$ group is named as ‘mercapto’ in the prefix (substituent).
3. 19. IUPAC rules for naming sulfides.
   1. xix. Naming is similar to ether; common name with the suffix as ‘sulfide’. If the compound has other functional group then ‘alkylthio’ is added as the substituent in the prefix.
4. 20. IUPAC rules for naming sulfoxide.
   1. xx. Naming is similar to sulfide; common name with the suffix as ‘sulfoxide’.

Answer to Problem 26PP

 IUPAC name is $\text{(E)-2-Ethoxy-3-methyl-2-pentene}$

Explanation of Solution

Predict the IUPAC nomenclature.

The IUPAC name must contain all the details regarding the structure of the compound. The structure of the ether contain a double bond (predict the configuration and include in the beginning of the name). The structure is categorized into larger group ( $\text{3-methylpentene}$) and smaller group (alkoxy- ethoxy). The position of the methyl substituent in the larger group is accounted by numbering the larger group (assign lowest priority for the substituents).

Here the larger group ( $\text{3-methylpentene}$) to be the parent alkane and the smaller group (ethoxy) as an alkoxy substituent. Finally, IUPAC name is $\text{(E)-2-Ethoxy-3-methyl-2-pentene}$.

(f)

Interpretation Introduction

Interpretation: For the given set of molecules the IUPAC name to be predicted.

Concept Introduction:

1. 21. IUPAC rules for naming ethers.
   1. xxi. Choose the larger group to be the parent alkane and naming the smaller group as an alkoxy substituent. Systematic names must be used for the complex ethers that exhibit multiple substituents and/or chirality centers.
2. 22. IUPAC rules for naming thiols.
   1. xxii. The nomenclature of thiol is similar to alcohol; thiol has $\text{SH}$ instead of $\text{OH}$ whereas the suffix of the name is ‘thiol’ instead of ‘ol’. If the compound containing other functional group then the $\text{SH}$ group is named as ‘mercapto’ in the prefix (substituent).
3. 23. IUPAC rules for naming sulfides.
   1. xxiii. Naming is similar to ether; common name with the suffix as ‘sulfide’. If the compound has other functional group then ‘alkylthio’ is added as the substituent in the prefix.
4. 24. IUPAC rules for naming sulfoxide.
   1. xxiv. Naming is similar to sulfide; common name with the suffix as ‘sulfoxide’.

Answer to Problem 26PP

 IUPAC name is $\text{1,2-dimethoxybenzene}$

Explanation of Solution

Predict the IUPAC nomenclature.

The IUPAC name must contain all the details regarding the structure of the compound. The structure is categorized into larger group (benzene) and smaller group (alkoxy- methoxy). The position of the two methoxy substituents in the larger group is accounted by numbering the larger group (assign lowest priority for the substituents).

Here the larger group (benzene) to be the parent alkane and the smaller group (two methoxy) as an alkoxy substituent. Finally, IUPAC name is $\text{1,2-dimethoxybenzene}$.

 (g)

Interpretation Introduction

Interpretation: For the given set of molecules the IUPAC name to be predicted.

Concept Introduction:

1. 25. IUPAC rules for naming ethers.
   1. xxv. Choose the larger group to be the parent alkane and naming the smaller group as an alkoxy substituent. Systematic names must be used for the complex ethers that exhibit multiple substituents and/or chirality centers.
2. 26. IUPAC rules for naming thiols.
   1. xxvi. The nomenclature of thiol is similar to alcohol; thiol has $\text{SH}$ instead of $\text{OH}$ whereas the suffix of the name is ‘thiol’ instead of ‘ol’. If the compound containing other functional group then the $\text{SH}$ group is named as ‘mercapto’ in the prefix (substituent).
3. 27. IUPAC rules for naming sulfides.
   1. xxvii. Naming is similar to ether; common name with the suffix as ‘sulfide’. If the compound has other functional group then ‘alkylthio’ is added as the substituent in the prefix.
4. 28. IUPAC rules for naming sulfoxide.
   1. xxviii. Naming is similar to sulfide; common name with the suffix as ‘sulfoxide’.

Answer to Problem 26PP

 IUPAC name is $\text{Ethyl}\text{propyl}\text{sulfide}$

Explanation of Solution

Predict the IUPAC nomenclature.

The IUPAC name must contain all the details regarding the structure of the compound (including position of substituents, configuration of chiral center and/or double bond). In the nomenclature of the sulfide which the structure is categorized into two substituents one is propyl and other is ethyl group. Nomenclature should contain both substituents arranged in the alphabetical order followed by the suffix ‘sulfide’.

Finally, IUPAC name is $\text{Ethyl}\text{propyl}\text{sulfide}$.