Organic Chemistry Lecture Notes

Practice Tests Overview

• Focus on reactions and mechanisms
• Multiple choice questions format

Question 1: Aldehyde Oxidation

• Reaction involves an aldehyde and silver oxide
• Silver ion (Ag⁺) can oxidize aldehydes to carboxylic acids
• Major product determined by acidic conditions (H₃O⁺) leading to protonated carboxylic acid
• Correct answer: B

Question 2: Radical Bromination

• Bromine in presence of UV light causes radical bromination
• Tertiary radicals are more stable than secondary
• Correct answer: C (bromine on tertiary carbon)

Bromination Reactions Review

• Br₂ with UV light or NBS is used for radical bromination
• Br₂ in dichloromethane results in anti-addition to double bonds
• Br₂ with FeBr₃ used for bromination of benzene rings

Question 3: Proton with Lowest pKa

• Comparison of acidity based on structure and functional groups
• Carboxylic acids generally have lower pKa than ketones
• Protonated acids are even more acidic
• Correct answer: D

Question 4: IR Spectra Analysis

• Identify functional groups based on IR peaks
• Carboxylic acids show broad OH peak (2500-3300 cm⁻¹) and carbonyl peak (~1700 cm⁻¹)
• Correct answer: B

Question 5: Para Nitro Benzoic Acid Synthesis

• Strategy focuses on directing groups and reaction sequence
• Ortho-para directors influence substitution pattern
• Correct answer: A (proper sequence of steps)

Conversion of Functional Groups

• Acid chloride to ester via alcohol reaction

Question 6: Ester Formation

• Acid chloride reacts with alcohol to form ester
• Grignard and Gilman reagents lead to different products
• Correct answer: C

Question 7: Wittig Reaction

• Converts ketones to alkenes
• Correct placement of double bond in final product
• Correct answer: D

Question 8: Diels-Alder Reaction

• Identifies diene and dienophile matching product
• Recognizes bicyclic product formation from cyclic diene
• Correct answer: B

Intramolecular Aldol Reaction

• Formation of rings via aldol condensation
• Heat causes dehydration and formation of enone

Question 9: Intramolecular Aldol Reaction

• Recognizes product formation based on aldol reaction conditions
• Correct answer: C

Question 10: Kinetic vs Thermodynamic Control

• Choice of base and temperature affects product outcome
• LDA and low temperature favor kinetic product
• Correct answer: A

Question 11: Electrophilic Aromatic Substitution

• Identifying more reactive aromatic ring for substitution
• Correct answer: B (bromination directed by stronger activator)

NMR Spectroscopy Basics

• Recognizing signals based on symmetry and hydrogen environments

Question 12: NMR Signal Counting

• Analysis based on number of unique hydrogen environments
• Correct answer: D

Question 13: Imines and Enamines

• Formation depends on primary vs secondary amine
• Correct answer: A

Aromaticity Criteria

• Huckel's rule (4n+2 rule)
• Planarity and conjugation necessary for aromaticity

Question 14: Aromatic vs Non-aromatic

• Identifying non-aromatic compound based on hybridization
• Correct answer: D

Question 15: Proton NMR Analysis

• Identifying compound based on NMR signal patterns
• Correct answer: D

General Tips

• Understand the role of reagents and conditions in reaction outcomes
• Pay attention to directing effects and hybridization in structural analysis
• Practice interpreting spectra and identifying functional groups