Ch. 4 - Alkanes and CycloalkanesWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Solution: Answer the following questions regarding cyclopropane and propane. a. Provide an approximate pKa value for the C-H bond of propane. b. Using pictures and a minimum amount of words, name and describe the types of strain associated with cyclopropane. c. The Csp3 orbitals are able to relieve some of the strain by adjusting slightly. Draw a molecular orbital representation of cyclopropane. d. Please provide a name for the type of “adjusted” bonds you drew in part c. e. Due to the reorganization of the hybrid orbitals in cyclopropane, the s character of the carbon-hydrogen bonds actually increases. Do you think this will increase or decrease the pKa value of a C-H bond in cyclopropane? Why or why not?

Solution: Answer the following questions regarding cyclopropane and propane. a. Provide an approximate pKa value for the C-H bond of propane. b. Using pictures and a minimum amount of words, name and describe

Problem

Answer the following questions regarding cyclopropane and propane.

a. Provide an approximate pKa value for the C-H bond of propane.

b. Using pictures and a minimum amount of words, name and describe the types of strain associated with cyclopropane.

c. The Csp3 orbitals are able to relieve some of the strain by adjusting slightly. Draw a molecular orbital representation of cyclopropane.

d. Please provide a name for the type of “adjusted” bonds you drew in part c.

e. Due to the reorganization of the hybrid orbitals in cyclopropane, the s character of the carbon-hydrogen bonds actually increases. Do you think this will increase or decrease the pKa value of a C-H bond in cyclopropane? Why or why not?