Textbook Question
Change the following condensed structures to Kekulé structures:
a. CH3NH(CH2)2CH3
b. (CH3)2CHCl
1647
views
Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
All textbooks
Bruice 8th EditionCh. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)Problem 32(1)
Bruice 8th EditionCh. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)Problem 32(1)Chapter 2, Problem 32(1)
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
Verified step by step guidance1
Step 1: Draw the Lewis structure for H₂CO₂. Start by identifying the total number of valence electrons. Carbon has 4 valence electrons, each hydrogen has 1 valence electron, and each oxygen has 6 valence electrons. Add these together to determine the total number of valence electrons available for bonding.
Step 2: Arrange the atoms with carbon as the central atom (since it is less electronegative than oxygen). Attach the two hydrogens and two oxygens to the carbon atom using single bonds. Distribute the remaining electrons to satisfy the octet rule for each atom, starting with the outer atoms (oxygen) and then the central atom (carbon).
Step 3: Check for formal charges on each atom. If necessary, adjust the structure by converting lone pairs on oxygen into double bonds with carbon to minimize formal charges and achieve the most stable structure. This will result in one oxygen atom being double-bonded to carbon and the other oxygen being single-bonded to carbon with a hydrogen attached to it.
Step 4: Describe the orbitals used by each carbon atom in bonding. Carbon in H₂CO₂ is sp² hybridized because it forms three sigma bonds (one with the double-bonded oxygen, one with the single-bonded oxygen, and one with a hydrogen atom) and has one unhybridized p orbital that participates in the π bond of the C=O double bond.
Step 5: Indicate the approximate bond angles. Since the carbon atom is sp² hybridized, the geometry around it is trigonal planar, and the bond angles are approximately 120°.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
6mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Lewis Structures
Lewis structures are diagrams that represent the bonding between atoms in a molecule and the lone pairs of electrons that may exist. They help visualize the arrangement of electrons and the connectivity of atoms, allowing for a better understanding of molecular geometry and reactivity. In the case of H2CO2, drawing the Lewis structure involves determining the total number of valence electrons and distributing them to satisfy the octet rule for each atom.
Recommended video:
Guided course
04:12
Drawing the Lewis Structure for N2H4.
Hybridization
Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate bonding. For carbon atoms in H2CO2, the hybridization can be determined based on the number of sigma bonds and lone pairs. For example, a carbon atom involved in double bonding typically exhibits sp2 hybridization, which influences the geometry and bond angles around the atom.
Recommended video:
Guided course
10:43Using bond sites to predict hybridization
Bond Angles
Bond angles are the angles formed between adjacent bonds in a molecule, which are influenced by the hybridization of the central atom and the presence of lone pairs. In H2CO2, the bond angles can be approximated based on the hybridization of the carbon atoms; for instance, sp2 hybridized carbon typically has bond angles around 120 degrees. Understanding bond angles is crucial for predicting the three-dimensional shape of the molecule.
Recommended video:
Guided course
02:46What is angle strain?
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.
1463
views
1
rank
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.
3. CCl4
1417
views
1
rank
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.
2. HCN
1137
views
1
rank
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.
4. H2CO3
1380
views
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.
2102
views