Assign an IUPAC name to each of the following compounds. a. CH 3 —(CH 2 ) 4 —SH b. CH 3 —(CH 2 ) 4 —OH

Question

Want to see more full solutions like this?

Answer 1

Textbook Question

Chapter 14, Problem 14.139EP

Assign an IUPAC name to each of the following compounds.

a. CH₃—(CH₂)₄—SH
b. CH₃—(CH₂)₄—OH

Chapter 14, Problem 14.139EP, Assign an IUPAC name to each of the following compounds. a. CH3(CH2)4SH b. CH3(CH2)4OH , example 1

Chapter 14, Problem 14.139EP, Assign an IUPAC name to each of the following compounds. a. CH3(CH2)4SH b. CH3(CH2)4OH , example 2

(a)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanethiol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−SH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 1

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is five carbon chain. Hence, the parent alkane is pentane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 2

The suffix -thiol is added to the parent alkane name. This gives the name as pentanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in first carbon atom. Therefore, the IUPAC name of the given compound is 1-pentanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 3

Conclusion

IUPAC name for the given compound is assigned.

(b)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−OH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 4

The longest continuous carbon chain with the hydroxyl group is found to be five carbon chain. Therefore, the parent alkane is pentane. As a hydroxyl group is present the name of the alcohol can be given as pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 5

The numbering has to be given so that the hydroxyl group gets the least numbering. In this case, the hydroxyl group is present in the first carbon atom. Therefore, the IUPAC name can be given as 1-pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 6

Conclusion

IUPAC name for the given compound is assigned.

(c)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanethiol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 7

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 8

The suffix -thiol is added to the parent alkane name. This gives the name as butanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 9

Conclusion

IUPAC name for the given compound is assigned.

(d)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 10

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 11

The suffix -ol is added to the parent alkane name by replacing the suffix “–e”. This gives the name as butanol.

Next step is to number the carbon atoms so that the hydroxyl functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 12

Conclusion

IUPAC name for the given compound is assigned.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Students have asked these similar questions

10. Stereochemistry. Assign R/S stereochemistry for the chiral center indicated on the following compound. In order to recieve full credit, you MUST SHOW YOUR WORK! H₂N CI OH CI カー 11. () Stereochemistry. Draw all possible stereoisomers of the following compound. Assign R/S configurations for all stereoisomers and indicate the relationship between each as enantiomer, diastereomer, or meso. NH2 H HNH, -18

b) 8. Indicate whether the following carbocation rearrangements are likely to occur Please explain your rational using 10 words or less not likely to occur • The double bond is still in the Same position + Likely to oc occur WHY? -3 H3C Brave Chair Conformers. Draw the chair conformer of the following substituted cyclohexane. Peform a RING FLIP and indicate the most stable conformation and briefly explain why using 20 words or less. CI 2 -cobs ?? MUST INDICATE H -2 -2 Br EQ Cl OR AT Br H& most stable WHY? - 4

CH 12 Conformational Analysis. Draw all 6 conformers (one above each letter) of the compound below looking down the indicated bond. Write the letter of the conformer with the HIGHEST and LOWEST in energies on the lines provided. NOTE: Conformer A MUST be the specific conformer of the structure as drawn below -4 NOT HOH OH 3 Conformer A: Br OH A Samo Br H 04 Br H H3 CH₂ H anti stagere Br CH clipsed H Brott H IV H MISSING 2 -2 B C D E F X 6 Conformer with HIGHEST ENERGY: 13. (1 structure LOWEST ENERGY: Nomenclature. a) Give the systematic (IUPAC) name structure. b) Draw the corresponding to this name. HINT: Do not forget to indicate stereochemistry when applicable. a) ८८ 2 "Br {t༐B,gt)-bemn€-nehpརི་ཚ༐lnoa Parent name (noname) 4 Bromo Sub = 2-methylethyl-4 Bromo nonane b) (3R,4S)-3-chloro-4-ethyl-2,7-dimethyloctane # -2 -2

Answer 2

Textbook Question

Chapter 14, Problem 14.139EP

Assign an IUPAC name to each of the following compounds.

a. CH₃—(CH₂)₄—SH
b. CH₃—(CH₂)₄—OH

Chapter 14, Problem 14.139EP, Assign an IUPAC name to each of the following compounds. a. CH3(CH2)4SH b. CH3(CH2)4OH , example 1

Chapter 14, Problem 14.139EP, Assign an IUPAC name to each of the following compounds. a. CH3(CH2)4SH b. CH3(CH2)4OH , example 2

(a)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanethiol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−SH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 1

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is five carbon chain. Hence, the parent alkane is pentane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 2

The suffix -thiol is added to the parent alkane name. This gives the name as pentanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in first carbon atom. Therefore, the IUPAC name of the given compound is 1-pentanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 3

Conclusion

IUPAC name for the given compound is assigned.

(b)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−OH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 4

The longest continuous carbon chain with the hydroxyl group is found to be five carbon chain. Therefore, the parent alkane is pentane. As a hydroxyl group is present the name of the alcohol can be given as pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 5

The numbering has to be given so that the hydroxyl group gets the least numbering. In this case, the hydroxyl group is present in the first carbon atom. Therefore, the IUPAC name can be given as 1-pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 6

Conclusion

IUPAC name for the given compound is assigned.

(c)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanethiol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 7

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 8

The suffix -thiol is added to the parent alkane name. This gives the name as butanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 9

Conclusion

IUPAC name for the given compound is assigned.

(d)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 10

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 11

The suffix -ol is added to the parent alkane name by replacing the suffix “–e”. This gives the name as butanol.

Next step is to number the carbon atoms so that the hydroxyl functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 12

Conclusion

IUPAC name for the given compound is assigned.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 3

Textbook Question

Chapter 14, Problem 14.139EP

Assign an IUPAC name to each of the following compounds.

a. CH₃—(CH₂)₄—SH
b. CH₃—(CH₂)₄—OH

Chapter 14, Problem 14.139EP, Assign an IUPAC name to each of the following compounds. a. CH3(CH2)4SH b. CH3(CH2)4OH , example 1

Chapter 14, Problem 14.139EP, Assign an IUPAC name to each of the following compounds. a. CH3(CH2)4SH b. CH3(CH2)4OH , example 2

(a)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanethiol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−SH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 1

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is five carbon chain. Hence, the parent alkane is pentane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 2

The suffix -thiol is added to the parent alkane name. This gives the name as pentanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in first carbon atom. Therefore, the IUPAC name of the given compound is 1-pentanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 3

Conclusion

IUPAC name for the given compound is assigned.

(b)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−OH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 4

The longest continuous carbon chain with the hydroxyl group is found to be five carbon chain. Therefore, the parent alkane is pentane. As a hydroxyl group is present the name of the alcohol can be given as pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 5

The numbering has to be given so that the hydroxyl group gets the least numbering. In this case, the hydroxyl group is present in the first carbon atom. Therefore, the IUPAC name can be given as 1-pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 6

Conclusion

IUPAC name for the given compound is assigned.

(c)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanethiol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 7

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 8

The suffix -thiol is added to the parent alkane name. This gives the name as butanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 9

Conclusion

IUPAC name for the given compound is assigned.

(d)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 10

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 11

The suffix -ol is added to the parent alkane name by replacing the suffix “–e”. This gives the name as butanol.

Next step is to number the carbon atoms so that the hydroxyl functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 12

Conclusion

IUPAC name for the given compound is assigned.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Textbook Question

Chapter 14, Problem 14.139EP

Assign an IUPAC name to each of the following compounds.

a. CH₃—(CH₂)₄—SH
b. CH₃—(CH₂)₄—OH

Chapter 14, Problem 14.139EP, Assign an IUPAC name to each of the following compounds. a. CH3(CH2)4SH b. CH3(CH2)4OH , example 1

Chapter 14, Problem 14.139EP, Assign an IUPAC name to each of the following compounds. a. CH3(CH2)4SH b. CH3(CH2)4OH , example 2

(a)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanethiol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−SH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 1

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is five carbon chain. Hence, the parent alkane is pentane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 2

The suffix -thiol is added to the parent alkane name. This gives the name as pentanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in first carbon atom. Therefore, the IUPAC name of the given compound is 1-pentanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 3

Conclusion

IUPAC name for the given compound is assigned.

(b)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−OH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 4

The longest continuous carbon chain with the hydroxyl group is found to be five carbon chain. Therefore, the parent alkane is pentane. As a hydroxyl group is present the name of the alcohol can be given as pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 5

The numbering has to be given so that the hydroxyl group gets the least numbering. In this case, the hydroxyl group is present in the first carbon atom. Therefore, the IUPAC name can be given as 1-pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 6

Conclusion

IUPAC name for the given compound is assigned.

(c)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanethiol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 7

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 8

The suffix -thiol is added to the parent alkane name. This gives the name as butanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 9

Conclusion

IUPAC name for the given compound is assigned.

(d)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 10

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 11

The suffix -ol is added to the parent alkane name by replacing the suffix “–e”. This gives the name as butanol.

Next step is to number the carbon atoms so that the hydroxyl functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 12

Conclusion

IUPAC name for the given compound is assigned.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Textbook Question

Answer 6

Textbook Question

Answer 7

(a)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanethiol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−SH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 1

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is five carbon chain. Hence, the parent alkane is pentane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 2

The suffix -thiol is added to the parent alkane name. This gives the name as pentanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in first carbon atom. Therefore, the IUPAC name of the given compound is 1-pentanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 3

Conclusion

IUPAC name for the given compound is assigned.

(b)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−OH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 4

The longest continuous carbon chain with the hydroxyl group is found to be five carbon chain. Therefore, the parent alkane is pentane. As a hydroxyl group is present the name of the alcohol can be given as pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 5

The numbering has to be given so that the hydroxyl group gets the least numbering. In this case, the hydroxyl group is present in the first carbon atom. Therefore, the IUPAC name can be given as 1-pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 6

Conclusion

IUPAC name for the given compound is assigned.

(c)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanethiol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 7

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 8

The suffix -thiol is added to the parent alkane name. This gives the name as butanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 9

Conclusion

IUPAC name for the given compound is assigned.

(d)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 10

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 11

The suffix -ol is added to the parent alkane name by replacing the suffix “–e”. This gives the name as butanol.

Next step is to number the carbon atoms so that the hydroxyl functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 12

Conclusion

IUPAC name for the given compound is assigned.

Answer 8

(a)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanethiol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−SH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 1

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is five carbon chain. Hence, the parent alkane is pentane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 2

The suffix -thiol is added to the parent alkane name. This gives the name as pentanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in first carbon atom. Therefore, the IUPAC name of the given compound is 1-pentanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 3

Conclusion

IUPAC name for the given compound is assigned.

Answer 9

(a)

Expert Solution

Answer 10

(a)

Expert Solution

Answer 11

Expert Solution

Answer 12

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer 13

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanethiol.

Answer 14

Explanation of Solution

Given structure of compound is CH3−(CH2)4−SH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 1

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is five carbon chain. Hence, the parent alkane is pentane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 2

The suffix -thiol is added to the parent alkane name. This gives the name as pentanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in first carbon atom. Therefore, the IUPAC name of the given compound is 1-pentanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 3

Answer 15

Conclusion

IUPAC name for the given compound is assigned.

Answer 16

(b)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanol.

Explanation of Solution

Given structure of compound is CH3−(CH2)4−OH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 4

The longest continuous carbon chain with the hydroxyl group is found to be five carbon chain. Therefore, the parent alkane is pentane. As a hydroxyl group is present the name of the alcohol can be given as pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 5

The numbering has to be given so that the hydroxyl group gets the least numbering. In this case, the hydroxyl group is present in the first carbon atom. Therefore, the IUPAC name can be given as 1-pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 6

Conclusion

IUPAC name for the given compound is assigned.

Answer 17

(b)

Expert Solution

Answer 18

(b)

Expert Solution

Answer 19

Expert Solution

Answer 20

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer 21

Answer to Problem 14.139EP

IUPAC name for the given compound is 1-pentanol.

Answer 22

Explanation of Solution

Given structure of compound is CH3−(CH2)4−OH. This can be drawn in expanded form as shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 4

The longest continuous carbon chain with the hydroxyl group is found to be five carbon chain. Therefore, the parent alkane is pentane. As a hydroxyl group is present the name of the alcohol can be given as pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 5

The numbering has to be given so that the hydroxyl group gets the least numbering. In this case, the hydroxyl group is present in the first carbon atom. Therefore, the IUPAC name can be given as 1-pentanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 6

Answer 23

Conclusion

IUPAC name for the given compound is assigned.

Answer 24

(c)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanethiol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 7

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 8

The suffix -thiol is added to the parent alkane name. This gives the name as butanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 9

Conclusion

IUPAC name for the given compound is assigned.

Answer 25

(c)

Expert Solution

Answer 26

(c)

Expert Solution

Answer 27

Expert Solution

Answer 28

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming thioalcohols that contain single thiol group:

• Longest carbon chain has to be identified that contains thiol group also. The chain name is obtained by adding the suffix “-thiol”. If the compound contains an unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the thiol group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the thiol group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.

IUPAC rules for naming thioalcohols that contain more than one thiol group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of thiol groups that is present.

Answer 29

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanethiol.

Answer 30

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 7

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 8

The suffix -thiol is added to the parent alkane name. This gives the name as butanethiol.

Next step is to number the carbon atoms so that the thiol functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanethiol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 9

Answer 31

Conclusion

IUPAC name for the given compound is assigned.

Answer 32

(d)

Expert Solution

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanol.

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 10

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 11

The suffix -ol is added to the parent alkane name by replacing the suffix “–e”. This gives the name as butanol.

Next step is to number the carbon atoms so that the hydroxyl functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 12

Conclusion

IUPAC name for the given compound is assigned.

Answer 33

(d)

Expert Solution

Answer 34

(d)

Expert Solution

Answer 35

Expert Solution

Answer 36

Interpretation Introduction

Interpretation:

IUPAC name for the given compound has to be assigned.

Concept Introduction:

IUPAC rules for naming alcohols that contain single hydroxyl group:

• Longest carbon chain has to be identified that contains hydroxyl group also. The chain name is obtained by replacing the letter “-e” in alkane with “-ol”. If the compound contains a unsaturated bond, then the respective name has to be changed with regard to alkane.
• The numbering has to be given so that the hydroxyl group gets the least numbering.
• Name and location of any other substituent present in the chain has to be identified.
• If in a ring the hydroxyl group is present, then that carbon is numbered 1 and the numbering then proceeds counterclockwise or clockwise in a way that substituents present if any gets the least numbering.
• Hydroxyl group as a substituent in a molecule is named as hydroxy group rather than hydroxyl group.
• If the compound contains bulky groups on same side of the double bond, then it is a cis isomer and if the bulkyl groups are present on opposite side of the double bond, then it is a trans isomer.
• In case of cycloalkane compounds, if the substitutions are present on same side of the ring of carbon atoms, it is a cis isomer. If the substitutions are present above and below the ring, then it is a trans isomer.

IUPAC rules for naming alcohols that contain more than one hydroxyl group:

• The same rules said above is followed but the prefix di-, tri-, tetra etc is added corresponding to the number of hydroxyl groups that is present.

Answer 37

Answer to Problem 14.139EP

IUPAC name for the given compound is 3-methyl-2-butanol.

Answer 38

Explanation of Solution

Given structure of compound is shown below,

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 10

First step is to identify the longest continuous carbon chain. In the given structure, it is found that the longest carbon chain is four carbon chain. Hence, the parent alkane is butane.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 11

The suffix -ol is added to the parent alkane name by replacing the suffix “–e”. This gives the name as butanol.

Next step is to number the carbon atoms so that the hydroxyl functional group gets the least numbering. In this case, it is in second carbon atom. Methyl group is present as substituent in the third carbon atom. Therefore, the IUPAC name of the given compound is 3-methyl-2-butanol.

Study Guide with Selected Solutions for Stoker's General, Organic, and Biological Chemistry, 7th, Chapter 14, Problem 14.139EP , additional homework tip 12