OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305582439
Author: Brown, William H.; Iverson, Brent L.; Anslyn, Eric; Foote, Christopher S.
Publisher: Cengage Learning
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Chapter 2, Problem 2.29P

For each IUPAC name, draw the corresponding structural formula and line-angle formula.

  1. (a) Ethanol
  2. (b) Butanal
  3. (c) Butanoic acid
  4. (d) Ethanoic acid
  5. (e) Heptanoic acid
  6. (f) Propanoic acid
  7. (g) Octanal
  8. (h) Cyclopentene
  9. (i) Cyclopentanol
  10. (j) Cyclopentanone
  11. (k) Cyclohexanol
  12. (l) Propanone

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Ethanol

Structural formula and line–angle formula:

From the name it is known that the compound has two carbon atoms.  The name ends with suffix –ol which indicates that there will be an alcoholic OH group in the compound.

The structural formula and line–angle formula for ethanol is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  1

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Butanal

Structural formula and line–angle formula:

From the name it is known that the compound has four carbon atoms.  The name ends with suffix –al which indicates that there will be an aldehyde CHO group in the compound.

The structural formula and line–angle formula for Butanal is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  2

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Butanoic acid

Structural formula and line–angle formula:

From the name it is known that the compound has four carbon atoms.  The name ends with suffix –oic acid which indicates that there will be an acid -COOH group in the compound.

The structural formula and line–angle formula for butanoic acid is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  3

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Ethanoic acid

Structural formula and line–angle formula:

From the name it is known that the compound has two carbon atoms.  The name ends with suffix –oic acid which indicates that there will be an acid -COOH  group in the compound.

The structural formula and line–angle formula for ethanoic acid is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  4

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Heptanoic acid

Structural formula and line–angle formula:

From the name it is known that the compound has seven carbon atoms.  The name ends with suffix –oic acid which indicates that there will be an acid -COOH  group in the compound.

The structural formula and line–angle formula for Heptanoic acid is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  5

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Propanoic acid

Structural formula and line–angle formula:

From the name it is known that the longest chain has three carbon atoms.  The name ends with suffix –oic acid which indicates that there will be an acid -COOH group in the compound.

The structural formula and line–angle formula for Propanoic acid is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  6

(g)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Octanal

Structural formula and line–angle formula:

From the name it is known that the longest chain has eight carbon atoms.  The name ends with suffix –al which indicates that there will be an aldehyde group in the compound.

The structural formula and line–angle formula for Octanal is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  7

(h)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Cyclopentene

Structural formula and line–angle formula:

From the name it is known main core of the compound has a five membered cyclic ring.  The name ends with suffix –ene which indicates that there will a double in the ring structure.

The structural formula and line–angle formula for Cyclopentene is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  8

(i)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Cyclopentanol

Structural formula and line–angle formula:

From the name it is known that the main core of the compound has a five membered cyclic ring.  The name ends with suffix –ol which indicates that there will be an alcoholic OH group in the compound.

The structural formula and line–angle formula for Cyclopentanol is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  9

(j)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Cyclopentanone

Structural formula and line–angle formula:

From the name it is known that the main core of the compound has five membered cyclic ring structure.  The name ends with suffix –one which indicates that there will be a ketone -C=O group in the compound.

The structural formula and line–angle formula for Cyclopentanone is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  10

(k)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Cyclohexanol

Structural formula and line–angle formula:

From the name it is known that the main core of the compound has six membered cyclic ring structure.  The name ends with suffix –ol which indicates that there will be an alcoholic -OH group in the compound.

The structural formula and line–angle formula for Cyclohexanol is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  11

(l)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

For the given IUPAC name, the corresponding structural formula and line–angle formula has to be drawn.

Concept Introduction:

Condensed structural formula:

Structural formula in which grouping of atoms are done and in which the central atoms along with the other atoms are connected to them are treated as group is known as Condensed structural formula.

Line–angle formula:

Structural formula where a line represent carbon‑carbon bond and the carbon atom is considered to be present in each point and the end of lines is known as Line-angle structural formula. This is a shorthand representation of an organic molecule with lines which represents its molecular bonding. In line–angle formula, hydrogen atoms are not shown.

Explanation of Solution

Given data:

Propanone

Structural formula and line–angle formula:

From the name it is known that the longest chain has three carbon atoms.  The name ends with suffix –one which indicates that there will be a ketone -C=O group in the compound.

The structural formula and line–angle formula for Propanone is drawn below.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.29P , additional homework tip  12

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Chapter 2 Solutions

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition

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
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