Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
bartleby

Videos

Textbook Question
Chapter 2, Problem 2.28P

Explain why each is an incorrect IUPAC name and write the correct IUPAC name for the intended compound.

  1. (a) 1,3-Dimethylbutane
  2. (b) 4-Methylpentane
  3. (c) 2,2-Diethylbutane
  4. (d) 2-Ethyl-3-methylpentane
  5. (e) 2-Propylpentane
  6. (f) 2,2-Diethylheptane
  7. (g) 2,2-Dimethylcyclopropane
  8. (h) 1-Ethyl-5-methylcyclohexane

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

  1. 1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
  2. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
  4. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
  6. 6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
  7. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1,3-Dimethylbutane

Correct IUPAC name:

The structure of 1,3-Dimethylbutane is,

Organic Chemistry, Chapter 2, Problem 2.28P , additional homework tip  1

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

  1. 1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
  2. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
  4. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
  6. 6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
  7. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

4-Methylpentane

Correct IUPAC name:

The structure of 4-Methylpentane is,

Organic Chemistry, Chapter 2, Problem 2.28P , additional homework tip  2

The given IUPAC name is incorrect because in the above structure, the pentane is numbered wrongly.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

  1. 1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
  2. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
  4. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
  6. 6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
  7. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylbutane

Correct IUPAC name:

The structure of 2,2-Diethylbutane is,

Organic Chemistry, Chapter 2, Problem 2.28P , additional homework tip  3

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group and one ethyl group at the third position

Hence, the correct IUPAC name is 3-ethyl-3-methylpentane.

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

  1. 1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
  2. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
  4. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
  6. 6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
  7. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2-Ethyl-3-methylpentane

Correct IUPAC name:

The structure of 2-Ethyl-3-methylpentane is,

Organic Chemistry, Chapter 2, Problem 2.28P , additional homework tip  4

The given IUPAC name is incorrect because in the above structure, the longest chain is hexane.

The main carbon chain has six carbon atoms and two methyl group at the third and fourth position

Hence, the correct IUPAC name is 3,4-dimethylhexane.

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

  1. 1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
  2. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
  4. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
  6. 6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
  7. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituents must be chosen as parent chain.

Explanation of Solution

Given data:

2-Propylpentane

Correct IUPAC name:

The structure of 2-Propylpentane is,

Organic Chemistry, Chapter 2, Problem 2.28P , additional homework tip  5

The given IUPAC name is incorrect because in the above structure, the longest chain is heptane.

The main carbon chain has seven carbon atoms and one methyl group at the fourth position

Hence, the correct IUPAC name is 4-methylheptane.

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

  1. 1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
  2. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
  4. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
  6. 6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
  7. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylheptane

Correct IUPAC name:

The structure of 2,2-Diethylheptane is,

Organic Chemistry, Chapter 2, Problem 2.28P , additional homework tip  6

The given IUPAC name is incorrect because in the above structure, the longest chain is octane.

The main carbon chain has eight carbon atoms and one methyl group and one ethyl group are at the second carbon.

Hence, the correct IUPAC name is 3-ethyl-3-methyloctane.

(g)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

  1. 1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
  2. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
  4. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
  6. 6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
  7. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Dimethylcyclopropane

Correct IUPAC name:

The structure of 2,2-Dimethylcyclopropane is,

Organic Chemistry, Chapter 2, Problem 2.28P , additional homework tip  7

The ring is numbered incorrectly for the above structure.

The main core of the given compound has a cyclic three membered ring with two methyl groups at one carbon.

Hence, the correct IUPAC name is 1,1-dimethylcylcopropane.

(h)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

  1. 1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
  2. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
  4. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
  6. 6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
  7. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1-Ethyl-5-methylcyclohexane

Correct IUPAC name:

The structure of 1-Ethyl-5-methylcyclohexane is,

Organic Chemistry, Chapter 2, Problem 2.28P , additional homework tip  8

The main core of the given compound has a cyclic six membered ring with one ethyl groups at first carbon and one methyl group at third carbon.

The main carbon chain has six carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 1-ethyl-3-methylcyclohexane.

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
The structure below has the formula C6H14 . Please name it according to IUPAC rules.
1-Propylamine, propan-1-ol, acetic acid, and butane have about the same molar masses. Which would you expect to have the (a) highest boiling point, (b) lowest boiling point, (c) least solubility in water, and (d) least chemical reactivity? Have each member of your group chose a part to answer, andthen discuss with each other why those answers were chosen.
predict the organic product when 1-pentanol is heated in the presence of a strong acid, H+. Include all hydrogen atoms.

Chapter 2 Solutions

Organic Chemistry

Ch. 2.5 - Draw a chair conformation of...Ch. 2.6 - Which cycloalkanes show cis, trans isomerism? For...Ch. 2.6 - Following is a planar hexagon representation for...Ch. 2.6 - Here is one cis,trans isomer of...Ch. 2.6 - Prob. AQCh. 2.6 - Prob. BQCh. 2.6 - Prob. CQCh. 2.7 - Arrange the alkanes in each set in order of...Ch. 2 - Write a line-angle formula for each condensed...Ch. 2 - Write the molecular formula of each alkane.Ch. 2 - Using parentheses and subscripts, provide an even...Ch. 2 - Which statements are true about constitutional...Ch. 2 - Prob. 2.20PCh. 2 - Each member of the following set of compounds is...Ch. 2 - Each of the following compounds is an amine...Ch. 2 - Each of the following compounds is either an...Ch. 2 - Draw structural formulas and write IUPAC names for...Ch. 2 - Draw structural formulas for all of the following....Ch. 2 - Write IUPAC names for these alkanes and...Ch. 2 - Write structural formulas and line-angle formulas...Ch. 2 - Explain why each is an incorrect IUPAC name and...Ch. 2 - For each IUPAC name, draw the corresponding...Ch. 2 - Write the IUPAC name for each compound.Ch. 2 - Prob. 2.31PCh. 2 - Torsional strain resulting from eclipsed CH bonds...Ch. 2 - How many different staggered conformations are...Ch. 2 - Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a...Ch. 2 - Consider 1-bromo-2-methylpropane and draw the...Ch. 2 - trans-1,4-Di-tert-butylcyclohexane exists in a...Ch. 2 - From studies of the dipole moment of...Ch. 2 - Prob. 2.38PCh. 2 - Following are the alternative chair conformations...Ch. 2 - Prob. 2.40PCh. 2 - Prob. 2.41PCh. 2 - Draw line-angle formulas for the cis and trans...Ch. 2 - Name and draw structural formulas for all...Ch. 2 - Using a planar pentagon representation for the...Ch. 2 - Gibbs free energy differences between...Ch. 2 - Prob. 2.46PCh. 2 - Calculate the difference in Gibbs free energy in...Ch. 2 - Draw the alternative chair conformations for the...Ch. 2 - Use your answers from Problem 2.48 to complete the...Ch. 2 - There are four cis,trans isomers of...Ch. 2 - Draw alternative chair conformations for each...Ch. 2 - 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans...Ch. 2 - Prob. 2.53PCh. 2 - What generalization can you make about the...Ch. 2 - What unbranched alkane has about the same boiling...Ch. 2 - Complete and balance the following combustion...Ch. 2 - Following are heats of combustion per mole for...Ch. 2 - Following are structural formulas and heats of...Ch. 2 - Without consulting tables, arrange these compounds...Ch. 2 - Which would you predict to have the larger (more...Ch. 2 - Following are structural formulas for 1,4-dioxane...Ch. 2 - Following is a planar hexagon representation of...Ch. 2 - On the left is a stereorepresentation of glucose...Ch. 2 - Prob. 2.64PCh. 2 - Prob. 2.65P
Knowledge Booster
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
    • SEE MORE QUESTIONS
    Recommended textbooks for you
  • Chemistry
    Chemistry
    ISBN:9781305957404
    Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
    Publisher:Cengage Learning
    Chemistry
    Chemistry
    ISBN:9781259911156
    Author:Raymond Chang Dr., Jason Overby Professor
    Publisher:McGraw-Hill Education
    Principles of Instrumental Analysis
    Chemistry
    ISBN:9781305577213
    Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
    Publisher:Cengage Learning
  • Organic Chemistry
    Chemistry
    ISBN:9780078021558
    Author:Janice Gorzynski Smith Dr.
    Publisher:McGraw-Hill Education
    Chemistry: Principles and Reactions
    Chemistry
    ISBN:9781305079373
    Author:William L. Masterton, Cecile N. Hurley
    Publisher:Cengage Learning
    Elementary Principles of Chemical Processes, Bind...
    Chemistry
    ISBN:9781118431221
    Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
    Publisher:WILEY
  • Chemistry
    Chemistry
    ISBN:9781305957404
    Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
    Publisher:Cengage Learning
    Chemistry
    Chemistry
    ISBN:9781259911156
    Author:Raymond Chang Dr., Jason Overby Professor
    Publisher:McGraw-Hill Education
    Principles of Instrumental Analysis
    Chemistry
    ISBN:9781305577213
    Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
    Publisher:Cengage Learning
    Organic Chemistry
    Chemistry
    ISBN:9780078021558
    Author:Janice Gorzynski Smith Dr.
    Publisher:McGraw-Hill Education
    Chemistry: Principles and Reactions
    Chemistry
    ISBN:9781305079373
    Author:William L. Masterton, Cecile N. Hurley
    Publisher:Cengage Learning
    Elementary Principles of Chemical Processes, Bind...
    Chemistry
    ISBN:9781118431221
    Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
    Publisher:WILEY
    07 Physical Properties of Organic Compounds; Author: Mindset;https://www.youtube.com/watch?v=UjlSgwq4w6U;License: Standard YouTube License, CC-BY