Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 2, Problem 2.27P

Write structural formulas and line-angle formulas for the following alkanes and cycloalkanes.

  1. (a) 2,2,4-Trimethylhexane
  2. (b) 2,2-Dimethylpropane
  3. (c) 3-Ethyl-2,4,5-trimethyloctane
  4. (d) 5-Butyl-2,2-dimethylnonane
  5. (e) 4-(1-Methylethyl)octane
  6. (f) 3,3-Dimethylpentane
  7. (g) trans-1,3-Dimethylcyclopentane
  8. (h) cis-1,2-Diethylcyclobutane

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formula and line–angle formula of the given compound has to be written.

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 compound:

2,2,4-Trimethylhexane

Structural formula and line–angle formula:

From the name, it is known that the main carbon chain has six carbon atoms and it has two methyl groups at the second carbon and one methyl group at the fourth carbon.

The structural formula and line–angle formula of the given compound is,

Organic Chemistry, Chapter 2, Problem 2.27P , additional homework tip  1

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formula and line–angle formula of the given compound has to be written.

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 compound:

2,2-Dimethylpropane

Structural formula and line–angle formula:

From the given name, it is clear that the main carbon chain has three carbon atoms and two methyl groups are at the second carbon.

The structural formula and line–angle formula of the given compound is,

Organic Chemistry, Chapter 2, Problem 2.27P , additional homework tip  2

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formula and line–angle formula of the given compound has to be written.

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 compound:

3-Ethyl-2,4,5-trimethyloctane

Structural formula and line–angle formula:

From the given name, it is clear that the main carbon chain has eight carbon atoms.  Three methyl groups are at second, fourth and fifth carbon and one ethyl group is at third carbon.

The structural formula and line–angle formula of the given compound is,

Organic Chemistry, Chapter 2, Problem 2.27P , additional homework tip  3

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formula and line–angle formula of the given compound has to be written.

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 compound:

5-Butyl-2,2-dimethylnonane

Structural formula and line–angle formula:

From the given name, the main carbon chain nine carbon atoms.  Two methyl groups are present at second carbon and one butyl groups is present at fifth carbon atom.

The structural formula and line–angle formula of the given compound is,

Organic Chemistry, Chapter 2, Problem 2.27P , additional homework tip  4

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formula and line–angle formula of the given compound has to be written.

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 compound:

4-(1-Methylethyl)octane

Structural formula and line–angle formula:

From the given name, it is clear that the main carbon chain has eight carbon atoms.  At the fourth carbon (1-methylethyl) group is attached.

The structural formula and line–angle formula of the given compound is,

Organic Chemistry, Chapter 2, Problem 2.27P , additional homework tip  5

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formula and line–angle formula of the given compound has to be written.

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 compound:

3,3-Dimethylpentane

Structural formula and line–angle formula:

From the name, it is clear that the main carbon chain has five carbon atoms and two methyl groups are attached at the third carbon.

The structural formula and line–angle formula of the given compound is,

Organic Chemistry, Chapter 2, Problem 2.27P , additional homework tip  6

(g)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formula and line–angle formula of the given compound has to be written.

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 compound:

trans-1,3-Dimethylcyclopentane

Structural formula and line–angle formula:

From the name of the compound, it is clear that the main core of the compound is a five membered cyclic ring.  Two methyl groups are attached at first and third carbon atom in such a way that both the methyl groups are in opposite direction of orientation with each other.

The structural formula and line–angle formula of the given compound is,

Organic Chemistry, Chapter 2, Problem 2.27P , additional homework tip  7

(h)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structural formula and line–angle formula of the given compound has to be written.

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 compound:

cis-1,2-Diethylcyclobutane

Structural formula and line–angle formula:

From the name of the compound, it is clear that the main core of the compound is a four membered cyclic ring.  Two ethyl groups are attached at first and second carbon atom in such a way that both the ethyl groups are in same direction of orientation with each other.

The structural formula and line–angle formula of the given compound is,

Organic Chemistry, Chapter 2, Problem 2.27P , additional homework tip  8

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(b) Draw structures corresponding to the following IUPAC names. (a) 3,4-Dimethylnonane (c) 2,2-Dimethyl-4-propyloctane (d) 2,2,4-Trimethylpentane (b) 3-Ethyl-4,4-dimethylheptane
Write condensed structures for the following compounds:(a) 4-tert-Butyl-2-methylheptane(b) 2,4-Dimethylpentane(c) 4,4-Diethyl-3-methyloctane(d) 3-Ethyl-1-isopropyl-5-methylcycloheptane(e) 1,1,3-Trimethylcyclopentane
Draw structures for the following molecules. (a) 2-iodo-2,3-dimethylheptane  (b) 4-cyclopropyl-3-ethyl-2-methyloctane  (c) 1-ethyl-2,4-dimethylcyclopentane

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
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