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Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
All textbooksBruice 8th EditionCh. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)Problem 22a,b
Chapter 2, Problem 22a,b

Change the following condensed structures to Kekulé structures:
a. CH3NH(CH2)2CH3
b. (CH3)2CHCl

Verified step by step guidance
1
Step 1: Understand the problem. The goal is to convert condensed structures into Kekulé structures, which are detailed representations showing all bonds explicitly, including single, double, and triple bonds, as well as lone pairs where applicable.
Step 2: For part (a), CH3NH(CH2)2CH3: Start by identifying the functional groups and connectivity. The molecule contains a methyl group (CH3), an amine group (NH), two methylene groups ((CH2)2), and another methyl group (CH3). Arrange these groups in a linear chain with explicit bonds.
Step 3: Draw the Kekulé structure for part (a). Begin with the central chain: CH3-NH-CH2-CH2-CH3. Represent all single bonds explicitly between the atoms, and show the lone pair on the nitrogen atom in the amine group.
Step 4: For part (b), (CH3)2CHCl: Identify the functional groups and connectivity. The molecule contains two methyl groups (CH3), a central carbon atom (C), and a chlorine atom (Cl). The central carbon is bonded to the two methyl groups and the chlorine atom.
Step 5: Draw the Kekulé structure for part (b). Represent the central carbon atom bonded to two methyl groups and one chlorine atom explicitly. Show all single bonds and the lone pairs on the chlorine atom.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Kekulé Structures

Kekulé structures are a way of representing organic molecules, particularly aromatic compounds, using lines to depict bonds between atoms. In these structures, carbon atoms are typically shown as vertices of lines, with hydrogen atoms implied. This representation helps visualize the connectivity and arrangement of atoms in a molecule, making it easier to understand its chemical properties and reactivity.
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Condensed Structural Formulas

Condensed structural formulas provide a simplified way to represent the structure of a molecule by grouping atoms together. In these formulas, atoms are written in a linear format, often indicating the connectivity without showing all the bonds explicitly. Understanding how to convert these condensed formulas into Kekulé structures is essential for visualizing the three-dimensional arrangement of atoms and the overall molecular geometry.
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Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups, such as amines or alkyl halides, is crucial when converting condensed structures to Kekulé structures, as they influence the bonding and overall structure of the compound. Identifying these groups helps in predicting the behavior and reactivity of the organic compounds.
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Related Practice
Textbook Question

Put a number in each of the blanks:

a. ___ s orbital and ___ p orbitals form ____ sp3 orbitals.

b. ___ s orbital and ___ p orbitals form ____ sp2 orbitals.

c. ___ s orbital and ___ p orbitals form ____ sp orbitals.

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1
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Textbook Question

Draw the lone-pair electrons that are not shown in the following condensed structures:

a. CH3CH2NH2

b. CH3NHCH3

c. CH3CH2OH

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Textbook Question

Draw condensed structures for the compounds represented by the following models (black = C, gray = H, red = O, blue = N, and green = Cl):

c. <IMAGE>

d. <IMAGE>

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Textbook Question

Draw condensed structures for the compounds represented by the following models (black = C, gray = H, red = O, blue = N, and green = Cl):

a. <IMAGE>

b. <IMAGE>

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Textbook Question

For each of the given species:

a. Draw its Lewis structure.

b. Describe the orbitals used by each carbon atom in bonding and indicate the approximate bond angles.

1. H2CO2

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Textbook Question

Explain why a σ bond formed by overlap of an s orbital with an sp3 orbital of carbon is stronger than a σ bond formed by overlap of an s orbital with a p orbital of carbon.

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