Organic Chemistry II Laboratory

Course Description

CHM2211L – Organic Chemistry II Laboratory is a 1-credit-hour laboratory course that accompanies CHM2211 (Organic Chemistry II lecture). Continuing the laboratory work begun in CHM2210L, this course advances students' competency in organic laboratory techniques and broadens experimental experience to include reactions and methods central to the second-semester organic chemistry curriculum: aromatic substitution, carbonyl chemistry, amines, biomolecules, multi-step synthesis, and advanced spectroscopic characterization.

Students perform more complex synthetic experiments — typically including multi-step syntheses requiring planning, execution across multiple lab sessions, and integrated characterization. The course emphasizes deeper engagement with NMR spectroscopy, IR spectroscopy, and chromatographic techniques, and develops scientific writing through more substantial laboratory reports approaching scientific publication style. Many programs also introduce literature searching and integration of primary scientific sources.

CHM2211L is a Florida common course offered at approximately 34 Florida institutions. It is required for chemistry majors, biochemistry majors, biology majors planning graduate study, and pre-medical, pre-dental, pre-pharmacy, pre-veterinary, and similar pre-health professional pathways. It is typically taken concurrently with CHM2211 (Organic Chemistry II lecture). It transfers as the equivalent course at all Florida public postsecondary institutions per SCNS articulation policy.

Learning Outcomes

Required Outcomes

Upon successful completion of this course, students will be able to:

• Continue to apply laboratory safety practices for organic chemistry, including expanded experience with reagents and procedures characteristic of second-semester organic.
• Apply fundamental organic laboratory techniques at expert level, including extraction, recrystallization, distillation, and chromatography.
• Plan and execute multi-step synthesis, including stepwise procedure development, intermediate characterization, and final product purification.
• Conduct experiments illustrating aromatic substitution (electrophilic aromatic substitution, including nitration, halogenation, Friedel-Crafts reactions where included).
• Conduct experiments illustrating carbonyl chemistry, including aldol reactions, Wittig reactions, Grignard additions, esterifications, and reduction/oxidation chemistry.
• Conduct experiments illustrating amines and amine-derived chemistry, including amine synthesis and acylation.
• Conduct experiments with biomolecules at the introductory level, which may include isolation of natural products, peptide chemistry, or carbohydrate chemistry.
• Apply infrared spectroscopy to confirm functional groups in synthetic products and starting materials.
• Apply proton NMR spectroscopy at intermediate level to determine structures, including chemical shift, integration, multiplicity, and coupling constants. Apply carbon-13 NMR at the introductory level (where instrumentation is available).
• Apply chromatographic techniques at intermediate level, including TLC for reaction monitoring and purity assessment, column chromatography for separations, and (where instrumentation available) gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS).
• Calculate and analyze yields for multi-step syntheses, including overall yield calculation and identification of limiting steps.
• Communicate experimental results in laboratory reports approaching scientific publication style, including appropriate format, scientific terminology, citation of primary sources, and discussion of results.
• Apply principles of green chemistry to organic laboratory practice where applicable.

Optional Outcomes

• Apply computational chemistry at intermediate level to predict properties, model reactions, and interpret spectra.
• Conduct literature-based investigation requiring database searching (SciFinder, Reaxys, Web of Science) and integration of primary scientific sources.
• Conduct an independent investigation or guided-inquiry project, possibly extending across multiple lab sessions.
• Engage with advanced spectroscopic instrumentation (FT-IR, NMR, GC-MS, HPLC, UV-vis) where institutional resources allow.
• Engage with biological and pharmaceutical applications of organic chemistry techniques.

Major Topics

Required Topics

• Continued Laboratory Safety: Reinforcement of safety habits; expanded experience with hazards (acid baths, strong oxidizers, lithium aluminum hydride and other reactive reagents, anhydrous solvents); emergency procedures.
• Advanced Laboratory Techniques: Inert atmosphere techniques (Schlenk line awareness, syringe technique); refluxing under inert atmosphere; vacuum filtration of reactive materials; Dean-Stark traps and azeotropic water removal; advanced extraction techniques.
• Multi-Step Synthesis: Planning a multi-step synthesis; managing intermediates; characterization at each step; stepwise yield analysis; troubleshooting failed steps; the role of multi-step synthesis in pharmaceutical and natural product chemistry.
• Aromatic Substitution Reactions: Electrophilic aromatic substitution experiments (nitration of methyl benzoate or similar; bromination; Friedel-Crafts acylation or alkylation where included); regiochemistry assessment; identifying products by spectroscopic methods.
• Aldol Reactions: Crossed aldol condensations; double aldol condensations; identifying products by spectroscopy.
• Wittig Reactions: Phosphonium ylide preparation; Wittig olefination; E/Z stereochemistry analysis (where applicable).
• Grignard Reactions: Preparation of Grignard reagents (with strict moisture exclusion); addition to carbonyl compounds (aldehydes, ketones, esters, CO₂); managing the air- and moisture-sensitive nature of the reaction.
• Esterification and Saponification: Fischer esterification; transesterification; basic hydrolysis (saponification); applications in soap-making and pharmaceutical chemistry.
• Reduction and Oxidation: Sodium borohydride reduction; lithium aluminum hydride reduction (where included); oxidation of alcohols (Jones, Swern at conceptual level, more commonly PCC, Dess-Martin); recognizing oxidation states.
• Amines: Reductive amination; amine acylation; imine and enamine chemistry; sulfonamide formation (where included).
• Diazonium Salt Chemistry (Where Included): Diazotization of aromatic amines; coupling reactions producing azo dyes; applications.
• Heterocyclic Chemistry (Introduction): Common heterocyclic ring systems (pyridine, pyrrole, furan, thiophene, indole, imidazole); their importance in pharmaceutical chemistry.
• Biomolecules: Carbohydrate chemistry experiments (where included — e.g., glucose oxidation, mutarotation); peptide chemistry (where included); natural product isolation (caffeine from tea, eugenol from cloves, limonene from citrus).
• Spectroscopy at Intermediate Level — IR: Functional group confirmation in synthetic products; comparing IR spectra of starting materials and products; identifying key diagnostic bands.
• Spectroscopy at Intermediate Level — Proton NMR: Assigning structures to NMR spectra; chemical shift databases; multiplicity analysis (n+1 rule); coupling constants and stereochemistry; advanced features (diastereotopic protons, conformational averaging at conceptual level).
• Spectroscopy at Intermediate Level — Carbon-13 NMR (Where Available): Carbon NMR concepts; DEPT experiments at conceptual level; combining proton and carbon NMR for structural elucidation.
• Mass Spectrometry (Introduction): Mass spectrometry concepts; molecular ion peak; common fragmentation patterns; relationship to molecular structure.
• Advanced Chromatography: Column chromatography for difficult separations; flash chromatography; gas chromatography (GC) and GC-MS interpretation (where instrumentation available).
• Scientific Writing: Lab reports approaching scientific publication format (Abstract, Introduction with literature context, Experimental, Results, Discussion with comparison to literature, Conclusion); citing primary scientific sources using ACS style; presenting spectra and chromatograms.

Optional Topics

• Computational Chemistry: Molecular modeling for predicting NMR shifts, IR frequencies, conformational analysis.
• Literature-Based Investigation: SciFinder or Reaxys searching; reading and citing primary literature; comparing experimental results to literature values.
• Independent or Guided-Inquiry Project: Extended student-driven investigation possibly across multiple lab sessions.
• Pharmaceutical Applications: Synthesis of pharmaceutical intermediates; structure-activity relationship discussions.
• Natural Product Isolation: More extensive natural product chemistry; steam distillation; large-scale isolation.

Resources & Tools

• Common Lab Manuals: Continuation of CHM2210L manuals — Macroscale and Microscale Organic Experiments (Williamson/Masters), Organic Chemistry Laboratory Manual (Pavia/Lampman/Kriz), Modern Projects and Experiments in Organic Chemistry (Mohrig)
• Lab Equipment: Standard organic chemistry equipment plus equipment for advanced techniques — Schlenk line or inert atmosphere setups (some institutions); GC and GC-MS instrumentation; HPLC (some institutions); UV-vis spectrophotometer; FT-IR; NMR (proton at minimum; many institutions have proton + carbon)
• Computational Resources: ChemDraw or comparable; Spartan, Avogadro, or institutional computational chemistry tools; SDBS Spectral Database for confirmation
• Reference Resources: SDBS (free); PubChem (free); ChemSpider (free); SciFinder (institutional); Reaxys (institutional); ACS Style Guide; Vogel's Textbook of Practical Organic Chemistry
• Reference Standards: American Chemical Society (ACS) Committee on Chemical Safety; OSHA Laboratory Standard (29 CFR 1910.1450); ACS Style Guide for chemical writing

Career Pathways

CHM2211L completes the standard organic chemistry laboratory sequence, the foundation for chemistry, biochemistry, life-science, and pre-health professional pathways. Specific career pathways supported include:

• Chemist (SOC 19-2031) — Industrial chemist roles in pharmaceuticals, agrochemicals, materials, food, cosmetics, petrochemicals.
• Biochemist and Biophysicist (SOC 19-1021) — Research and applied roles in biotechnology and pharmaceuticals.
• Pharmaceutical and Biotechnology Industry — Florida pharmaceutical and biotechnology employers.
• Pre-Health Professional Pathways — Required for pre-medical (MCAT covers organic chemistry), pre-dental, pre-veterinary, pre-pharmacy, pre-physician assistant pathways.
• Forensic Science — Forensic chemistry, drug analysis, toxicology.
• Environmental Chemistry — Water quality, soil testing, environmental remediation.
• Quality Control Chemistry — Manufacturing QC.
• Education — Foundation for high school and college chemistry teaching.
• Graduate Study in Chemistry, Biochemistry, and Allied Sciences — CHM2211L is foundational for graduate-level laboratory work in chemistry and life sciences.

Special Information

General Education and Transfer

CHM2211L is a Florida common course number that transfers as the equivalent course at all Florida public postsecondary institutions per SCNS articulation policy. Together with CHM2211 (Organic Chemistry II lecture), it satisfies the second-semester organic chemistry requirement at most Florida programs.

Concurrent Enrollment with CHM2211

CHM2211L is typically taken concurrently with or immediately after CHM2211 (Organic Chemistry II lecture). Concurrent enrollment is the standard pathway. Some institutions require simultaneous enrollment.

Course Sequence

CHM2211L (with CHM2211) is the second half of the standard two-semester organic chemistry lab sequence (CHM2210L + CHM2211L). Students continuing in chemistry typically progress to physical chemistry, analytical chemistry, biochemistry, and instrumental analysis courses.

Prerequisite Requirements

Students entering CHM2211L typically must have completed:

• CHM2210 (Organic Chemistry I lecture) with grade of C or better
• CHM2210L (Organic Chemistry I lab) with grade of C or better
• Co-enrollment in CHM2211 (Organic Chemistry II lecture)

Lab Safety Considerations

CHM2211L involves work with reagents that pose more substantial hazards than those typically encountered in CHM2210L (acid baths for nitration, lithium aluminum hydride for some reductions, anhydrous solvents and inert atmosphere for organometallic reactions). Strict adherence to safety protocols is essential. Students with allergies, sensitivities, or other medical concerns should consult their instructor at the start of the term. Pregnant students should consult their healthcare provider regarding specific exposure concerns.

Course Format

CHM2211L typically meets weekly for 3-4 hours of laboratory work. The course is offered primarily in face-to-face format due to the hands-on nature of the work and the importance of using advanced instrumentation; fully online versions are uncommon.