Ch. 14 - Synthetic TechniquesWorksheetSee 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
Sections
Synthetic Cheatsheet
Moving Functionality
Alkynide Alkylation
Alkane Halogenation
Retrosynthesis

Solution: Compound A has molecular formula C5H10. When A is treated with BH3, followed by H2O2, NaOH, H2O, a mixture of B and B’ is isolated. B and B’ each have molecular formula C5H12O. Separately, B and B’ are optically active. A 50:50 mixture of B and B’ is optically inactive, however. When the mixture of B and B’ is exposed to the Jones reagent (CrO3, H2SO4, H2O), a single compound C (C5H10O) is produced. Finally, when A is treated with O3 followed by H2O2, acetone (shown below) and Compound D (C2H4O2) are produced. Complete the reaction scheme below by drawing structures for the unknown compounds A, B, B’, C and D. Be sure to show the stereochemistry of B and B’ clearly and unambiguously!

Problem

Compound A has molecular formula C5H10. When A is treated with BH3, followed by H2O2, NaOH, H2O, a mixture of B and B’ is isolated. B and B’ each have molecular formula C5H12O. Separately, B and B’ are optically active. A 50:50 mixture of B and B’ is optically inactive, however. When the mixture of B and B’ is exposed to the Jones reagent (CrO3, H2SO4, H2O), a single compound C (C5H10O) is produced. Finally, when A is treated with O3 followed by H2O2, acetone (shown below) and Compound D (C2H4O2) are produced. Complete the reaction scheme below by drawing structures for the unknown compounds A, B, B’, C and D. Be sure to show the stereochemistry of B and B’ clearly and unambiguously!