Questions and Answers
What is the definition of an aldehyde?
What is a constitutional isomer?
A compound with the same atoms but different atoms bonded to each other.
What are stereoisomers?
Molecules with the same atoms differing only in 3D configuration.
What are enantiomers?
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What are diastereomers?
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What does 'R' represent in stereochemistry?
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What does 'S' represent in stereochemistry?
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What does 'cis' mean in stereochemistry?
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What does 'trans' mean in stereochemistry?
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What does 'E' indicate in reference to alkenes?
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What does 'Z' indicate in reference to alkenes?
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What is ortho substitution?
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What is meta substitution?
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What is para substitution?
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What is the protocol for naming esters?
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What is the difference between benzyl and phenyl?
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What is aniline?
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What is Huckel's equation?
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Do lone pairs contribute to hybridization?
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How do you draw a Lewis structure?
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How is free energy related to acidity?
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What is the Gibbs free energy equation for an acid reaction?
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What factors influence acidity?
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How do electron withdrawing groups influence acidity?
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In terms of stability, which orbital holds a lone pair best?
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Which is more stable for an acid: resonance in a ring or resonance with a carbonyl?
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In an acid, does a smaller pKa mean more or less acidic?
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What is a racemic mixture?
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What is a meso compound?
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What is the difference between conformations and configurations?
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Is the boiling point of a racemic mixture the same as that of each pure enantiomer?
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What types of reactions do strong bases tend towards?
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Rank the stability of carbocations from most to least stable.
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Greater size = ________ nucleophile
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How do allyl or benzyl groups affect the speed of an SN2 reaction?
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Do phenols undergo substitution reactions?
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How does protonation affect epoxide reactions?
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The H atom in an elimination in a ring must be in the same plane as the leaving group.
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How do polar protic solvents affect SN1, SN2, E1, and E2 reactions?
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How does the size of a molecule affect nucleophilicity in polar protic vs polar aprotic solvents?
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Do non-polar solvents favor unimolecular or bimolecular mechanisms in substitution elimination reactions?
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Does heat favor substitution or elimination?
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What is an imine and how is it formed?
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What is an enamine and how is it formed?
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What is the first step in acetal formation?
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What are the substituents of an acetal?
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Can ethers be hydrolyzed under mildly acidic conditions?
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Can NaBH4 reduce carboxylic acids/esters?
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Weaker bases lead to more 1,4 or 1,2 additions in vinyl ketones?
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Is a nitrogen atom with three different groups chiral?
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How do organocuprates react with carbonyl carbons and alkenes?
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When are chromium agents used for oxidation and manganese agents?
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What types of chromium agents partially oxidize and give examples?
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What is the haloform reaction?
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How does ozone react with alkenes?
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What does periodic acid cleave?
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Study Notes
Functional Groups and Basic Terminology
- Aldehyde: Compound with the -al suffix.
- Alcohol: Compound with the -ol or hydroxy- prefix.
- Ketone: Compound with the -one suffix.
- Carboxylic acid: Compound ending in -oic acid.
- Ester: Compound with the -oate suffix.
- Ether: Compound with the ether or alkoxy- prefix.
- Alkyl halides: Compounds including halogen atoms (i.e., Iodo-, Bromo-).
- Amide: Compounds ending in -amide.
- Amine: Compounds with amino- or -amine groups.
Isomerism
- Constitutional isomer: Compounds with the same atoms but different bonding arrangements.
- Stereoisomers: Molecules differing only in three-dimensional arrangement of atoms.
- Enantiomers: Stereoisomers that are non-superimposable mirror images at all stereogenic centers.
- Diastereomers: Stereoisomers with changes in configuration at some, but not all, stereogenic carbons.
Stereochemical Notation
- R: Clockwise configuration at a stereogenic center.
- S: Counterclockwise configuration at a stereogenic center.
- cis: Refers to groups on the same side in a double bond or ring.
- trans: Refers to groups on opposite sides in a double bond or ring.
- E: Trans configuration in alkenes.
- Z: Cis configuration in alkenes.
- Ortho: 1,2 substitution pattern on a benzene ring.
- Meta: 1,3 substitution pattern on a benzene ring.
- Para: 1,4 substitution pattern on a benzene ring.
Naming Protocols
- Esters: Named using the alkyl from the alcohol first, followed by the alkyl from the carbonyl ending in "-oate."
- Substituted amides: Begin with the name of the nitrogen-substituted group followed by the carbonyl group ending in "-amide."
Huckel's Rule
- Equation: Huckel's numbers = 4n + 2.
- Significance: Determines the number of pi electrons in aromatic systems.
Lewis Structures
- Draw by calculating total valence electrons and arranging to complete octets around each atom.
Acidity Concepts
- Relationship between free energy and acidity: Lower free energy in proton loss indicates higher acidity.
- Gibbs free energy equation for acids: ΔG = -RTln([A-][H3O+]/[HA][H2O]).
- Acidity factors: Analyzed using MARIO minus M (Atom, Resonance, Induction, Orbitals).
Nucleophilicity and Mechanisms
- Strong bases prefer SN2 or E2 reactions.
- Nucleophilicity improves with molecule size in polar protic solvents; larger nucleophiles are favored.
- Non-polar solvents enhance bimolecular mechanisms by preventing charged leaving groups from departing.
Reaction Dynamics
- Heat favors elimination reactions over substitution.
- Protonation of epoxides allows for nucleophile attack at more substituted carbons.
- Racemic mixtures have different boiling points compared to pure enantiomers.
Specialized Compounds
- Imine: Formed from carbonyl carbon and ammonia, results in C=N bond.
- Enamine: Alkene connected to a substituted amine through carbonyl attack.
Oxidation Agents Usage
- Chromium agents are effective in acidic conditions; manganese agents are used in basic conditions.
- Anhydrous chromium agents like PCC provide partial oxidation compared to complete oxidation from others.
Reactions and Cleavage
- Haloform reaction converts methyl ketones into carboxylic acids via halogenation and neutralization.
- Ozone cleavage of alkenes produces ketones and aldehydes.
- Periodic acid cleaves cis-1,2-diols.
Miscellaneous
- The first step in acetal formation involves protonation of oxygen.
- Stability potential of lone pairs follows sp > sp2 > sp3 in hybridization, influencing acidity trends.
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Description
This study guide consists of flashcards designed to help students review essential concepts in organic chemistry, including functional groups and isomer types. Whether you're preparing for an exam or looking to reinforce your understanding, these flashcards cover key terms and definitions that are crucial for first-semester organic chemistry.