Skip to main content
Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
Chapter 1, Problem 23

Convert the models in Problem 20 to skeletal structures.
a. <IMAGE>
b. <IMAGE>
c. <IMAGE>
d. <IMAGE>

Verified step by step guidance
1
Step 1: Analyze the first model (image a). Identify the atoms and bonds. The structure contains two carbon atoms bonded together, with one carbon attached to three hydrogens and the other bonded to two hydrogens and a chlorine atom. Convert this to a skeletal structure by representing the carbon-carbon bond as a line and omitting hydrogen atoms bonded to carbons.
Step 2: Examine the second model (image b). This structure includes a carbonyl group (C=O) attached to a carbon atom, which is bonded to another carbon atom. The second carbon is bonded to three hydrogens. Convert this to a skeletal structure by representing the carbon-carbon bonds as lines and showing the carbonyl group explicitly.
Step 3: Analyze the third model (image c). This structure contains a carbonyl group (C=O) attached to a carbon atom, which is bonded to a nitrogen atom. The nitrogen atom is bonded to another carbon atom, which is connected to two methyl groups. Convert this to a skeletal structure by representing the carbon-carbon and carbon-nitrogen bonds as lines, showing the carbonyl group explicitly, and representing the methyl groups as branches.
Step 4: Examine the fourth model (image d). This structure contains a triple bond between a carbon and a nitrogen atom. The carbon is bonded to another carbon atom, which is bonded to three hydrogens. Convert this to a skeletal structure by representing the carbon-carbon bond as a line and the carbon-nitrogen triple bond explicitly.
Step 5: Ensure all skeletal structures are drawn correctly by verifying the number of bonds around each atom matches its valency (e.g., carbon forms four bonds, nitrogen forms three bonds, etc.). Double-check that hydrogens are omitted in the skeletal structure unless attached to heteroatoms like oxygen or nitrogen.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
4m
Was this helpful?

Key Concepts

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

Skeletal Structures

Skeletal structures are simplified representations of organic molecules that depict only the carbon backbone and functional groups. In these diagrams, carbon atoms are represented by vertices or ends of lines, while hydrogen atoms attached to carbons are usually omitted for clarity. This method allows chemists to quickly visualize the molecular framework and identify functional groups without the clutter of hydrogen atoms.
Recommended video:
Guided course
04:03
How bondline is different from Lewis Structures.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. They determine the properties and reactivity of organic compounds. Common functional groups include hydroxyl (-OH), carboxyl (-COOH), and amine (-NH2), and recognizing them is crucial for understanding the behavior of organic molecules in chemical reactions.
Recommended video:
Guided course
02:36
Identifying Functional Groups

Bonding and Hybridization

Bonding and hybridization are fundamental concepts in organic chemistry that describe how atoms connect to form molecules. Hybridization involves the mixing of atomic orbitals to create new hybrid orbitals, which can form sigma bonds with other atoms. Understanding the types of bonds (single, double, triple) and the geometry of hybridized orbitals is essential for predicting molecular shapes and reactivity.
Recommended video:
Guided course
10:43
Using bond sites to predict hybridization