Ch. 15 - Analytical Techniques: IR, NMR, Mass SpectWorksheetSee 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: If you did not know the regioselectivity leading to the major product in the Birch reduction of toluene, but you did know that a 1,4-cyclohexadiene is formed, the structural formulas of the two possib

Problem

If you did not know the regioselectivity leading to the major product in the Birch reduction of toluene, but you did know that a 1,4-cyclohexadiene is formed, the structural formulas of the two possible major products are given to the right. To learn which one is indeed the major product, one could record the proton-decoupled 13C NMR spectrum of the isolated major product of the reaction. Clearly and concisely describe how you can learn from a quick, and not very involved analysis, of the proton-decoupled 13C NMR spectrum whether the major product is 1-methyl-1,4-cyclohexadiene or 3-methyl-1,4-cyclohexadiene. Most obviously, how would the proton-decoupled 13C NMR spectrum of 1-methyl-1,4-cyclohexadiene differ from the proton-decoupled 13C NMR spectrum of 3-methyl-1,4- cyclohexadiene?