Chem 341 Review for Finals Structure Determination

1
Chem 341 Review for FinalsStructure Determination

• NMR
• Chemical shifts, splitting patterns,
  integrations
• IR
• ROH, CO
• Formula gt of Rings Pi-Bonds

2
Chem 341 Review for FinalsStructure and Bonding

• s- Bonds p-Bonds
• Resonance Structures
• Aromaticity
• Heterocycles
• Pyramidal Amines Flat Amides
• Cyclohexane

3
Chem 341 Review for FinalsPhysical
PropertiesBoiling Points and Water Solubility

• Hydrocarbons
• weak forces, van der Waals Attraction
• Ethers, Ketones, Esters, Halides
• medium strength attraction dipoles
• Alcohols, Acids, Amides
• strong attraction hydrogen bonds

4
Chem 341 Review for FinalsIsomers

• Structural Isomers
• Stereoisomers
• Enantiomers (Chirality R/S nomenclature)
• Diastereomers (meso isomers)
• epimers and anomers
• tautomers ketones and enols

5
Chem 341 Review for FinalsClasses of Compounds

• Synthetic Polymers
• Polyesters, Polyamides,
• Radical Polymerization of alkenes
• Lipids and Detergents
• Fats, Waxes, Soaps, Detergents, miceles,
  Phospholipid bi-layers
• Carbohydrates
• hexose, pentose, furanose, pyranose, aldose,
  ketose,
• di- and polysaccharides, anomeric center

6
Chem 341 Review for FinalsClasses of Compounds

• Amino Acids
• acidic, basic, neutral
• isoelectric point
• peptides and proteins
• Nucleotides and Nucleic Acids
• purine and pyrimidine bases
• ribose and deoxyribose
• phosphate links between sugars
• hydrogen bonding of base pairs

7
Chem 341 Review for FinalsAcidity

• pKa and pH relationships
• Alcohols - phenols - carboxylic acids
• Alkyl amines - aryl amines
• Amino Acids
• Isoelectric point

8
Chem 341 Review for FinalsReaction Types

• Reaction Energy Diagrams
• Additions to Alkenes
• H2, HBr, Br2
• Electrophilic Aromatic Substitution
• (ortho/para vs meta directing groups)
• - Nitration, bromination, alkylation,
  sulfonation, alkylation, acylation

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Chem 341 Review for FinalsReaction Types

• Reaction Energy Diagrams
• Additions to Alkenes
• H2, HBr, Br2
• Reactions of Organic Halides
• Sn1, Sn2, E2
• Carbocation stabilities

10
Chem 341 Review for FinalsReaction Types

• Reactions of Alcohols
• Dehydration, conversion to alkyl halides
• Oxidation of alcohols to aldehydes or acids
• Concept of oxidizing and reducing agents
• Ether Synthesis
• Epoxide ring opening

11
Chem 341 Review for FinalsReaction Types

• RMgBr (Grignard Reagents)
• Preparation from alkyl halides
• Reactions with aldehydes, ketones, and esters
• Nucleophilic Addition to Ketones
• Irreversible additions LiAlH4 RMgBr
• Reversible additions alcohols gt hemiacetal
  acetal
• Addition-Elimination amines gt imines

12
Chem 341 Review for FinalsReaction Types

• Reactions involving Enol Intermediates
• Exchange of ketone a-hydrogens with D2O
• Aldol condensation addition of enolate anion
  to an aldehyde carbonyl carbon
• Carboxylic acid derivatives
• Relative reactivity
• Acid halides gt Anhydrides gt Esters gt Amides gt
• Synthesis and Hydrolysis of Esters and Amides
• Reactions of Esters with RMgBr and LiAlH4

13
Chem 341 Review for FinalsReaction Types

• Reactions of Amines
• Carbohydrates
• Reactions interconverting aldehydes and cyclic
  hemiacetals, the anomeric center

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Chem 341 Review for FinalsKey Reactions
Mechanisms

• Electrophilic Addition to Alkenes
• HBr Addition to 1-hexene
• SN2 Reaction
• amine reaction with 1 halide
• SN1 Reaction
• water reaction with 3 halide

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Chem 341 Review for FinalsKey Reactions
Mechanisms

• E2 Elimination
• base reaction with a 2 halide to give alkene
• Electrophilic Aromatic Substitution
• nitration of benzene
• Hemiacetal Formation
• Acid catalyzed reaction of alcohols with
  aldehydes to give hemiacetal (sugars)

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Chem 341 Review for FinalsKey Reactions
Mechanisms

• Nucleophilic addition to Carbonyl Groups
• Base catalyzed hydrolysis of esters
• Acid Catalyzed Esterification
• Synthesis of esters from acids and alcohols
• Aldol Condensation
• enolate anion addition to carbonyl carbon