ACS Organic Chemistry Flashcards
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Questions and Answers

What is the definition of an aldehyde?

  • Alcohol
  • Compounds with a carbonyl group at the end of the carbon chain (correct)
  • Ketone
  • Carboxylic acid

    • 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?

    <p>Stereoisomers with exactly opposite stereochemical designations at all stereogenic carbons.</p> Signup and view all the answers

    What are diastereomers?

    <p>Stereoisomers with several changes in the stereochemical designations of stereogenic carbons.</p> Signup and view all the answers

    What does 'R' represent in stereochemistry?

    <p>Clockwise.</p> Signup and view all the answers

    What does 'S' represent in stereochemistry?

    <p>Counterclockwise.</p> Signup and view all the answers

    What does 'cis' mean in stereochemistry?

    <p>Same.</p> Signup and view all the answers

    What does 'trans' mean in stereochemistry?

    <p>Different.</p> Signup and view all the answers

    What does 'E' indicate in reference to alkenes?

    <p>Trans.</p> Signup and view all the answers

    What does 'Z' indicate in reference to alkenes?

    <p>Cis.</p> Signup and view all the answers

    What is ortho substitution?

    <p>1,2 substitution.</p> Signup and view all the answers

    What is meta substitution?

    <p>1,3 substitution.</p> Signup and view all the answers

    What is para substitution?

    <p>1,4 substitution.</p> Signup and view all the answers

    What is the protocol for naming esters?

    <p>Identify alkyl from substituted alcohol, followed by alkyl from carbonyl ending in '-oate'.</p> Signup and view all the answers

    What is the difference between benzyl and phenyl?

    <p>Benzyl: ring + CH2; Phenyl: ring.</p> Signup and view all the answers

    What is aniline?

    <p>Ring + NH2.</p> Signup and view all the answers

    What is Huckel's equation?

    <p>4n + 2.</p> Signup and view all the answers

    Do lone pairs contribute to hybridization?

    <p>True</p> Signup and view all the answers

    How do you draw a Lewis structure?

    <p>Determine the number of valence electrons, attempt to form octets.</p> Signup and view all the answers

    How is free energy related to acidity?

    <p>Decreasing free energy implies more stability in products, indicating higher acidity.</p> Signup and view all the answers

    What is the Gibbs free energy equation for an acid reaction?

    <p>Delta G = -RTln([A-][H3O+]/[HA][H2O]).</p> Signup and view all the answers

    What factors influence acidity?

    <p>MARIO minus M (Atom, Resonance, Induction, Orbitals).</p> Signup and view all the answers

    How do electron withdrawing groups influence acidity?

    <p>Increase an acid's ability to donate a proton.</p> Signup and view all the answers

    In terms of stability, which orbital holds a lone pair best?

    <p>sp &gt; sp2 &gt; sp3.</p> Signup and view all the answers

    Which is more stable for an acid: resonance in a ring or resonance with a carbonyl?

    <p>Carbonyl.</p> Signup and view all the answers

    In an acid, does a smaller pKa mean more or less acidic?

    <p>More acidic.</p> Signup and view all the answers

    What is a racemic mixture?

    <p>Equal concentrations of enantiomers.</p> Signup and view all the answers

    What is a meso compound?

    <p>A molecule with two or more stereocenters containing an internal mirror plane.</p> Signup and view all the answers

    What is the difference between conformations and configurations?

    <p>Conformations are rotated molecules around single bonds; configurations require bond breaking.</p> Signup and view all the answers

    Is the boiling point of a racemic mixture the same as that of each pure enantiomer?

    <p>False</p> Signup and view all the answers

    What types of reactions do strong bases tend towards?

    <p>SN2 or E2.</p> Signup and view all the answers

    Rank the stability of carbocations from most to least stable.

    <p>Tertiary &gt; Secondary &gt; Primary &gt; Methyl.</p> Signup and view all the answers

    Greater size = ________ nucleophile

    <p>Stronger.</p> Signup and view all the answers

    How do allyl or benzyl groups affect the speed of an SN2 reaction?

    <p>Increase speed.</p> Signup and view all the answers

    Do phenols undergo substitution reactions?

    <p>False</p> Signup and view all the answers

    How does protonation affect epoxide reactions?

    <p>If the oxygen is protonated, the nucleophile will attack the more substituted carbon.</p> Signup and view all the answers

    The H atom in an elimination in a ring must be in the same plane as the leaving group.

    <p>True</p> Signup and view all the answers

    How do polar protic solvents affect SN1, SN2, E1, and E2 reactions?

    <p>Stabilize carbocation intermediates in SN1 and E1; do not hinder E2, but block SN2.</p> Signup and view all the answers

    How does the size of a molecule affect nucleophilicity in polar protic vs polar aprotic solvents?

    <p>Larger size in polar protic increases nucleophilicity; smaller size in polar aprotic increases nucleophilicity.</p> Signup and view all the answers

    Do non-polar solvents favor unimolecular or bimolecular mechanisms in substitution elimination reactions?

    <p>True</p> Signup and view all the answers

    Does heat favor substitution or elimination?

    <p>False</p> Signup and view all the answers

    What is an imine and how is it formed?

    <p>An imine is C=N:-H, formed via attack of a carbonyl carbon by ammonia or a derivative.</p> Signup and view all the answers

    What is an enamine and how is it formed?

    <p>An enamine is an alkene + a (substituted, usually) amine formed when an amine attacks a carbonyl.</p> Signup and view all the answers

    What is the first step in acetal formation?

    <p>Protonation of the oxygen.</p> Signup and view all the answers

    What are the substituents of an acetal?

    <p>-OR, -OR, -R, -H.</p> Signup and view all the answers

    Can ethers be hydrolyzed under mildly acidic conditions?

    <p>No.</p> Signup and view all the answers

    Can NaBH4 reduce carboxylic acids/esters?

    <p>False</p> Signup and view all the answers

    Weaker bases lead to more 1,4 or 1,2 additions in vinyl ketones?

    <p>1,4.</p> Signup and view all the answers

    Is a nitrogen atom with three different groups chiral?

    <p>False</p> Signup and view all the answers

    How do organocuprates react with carbonyl carbons and alkenes?

    <p>Organocuprates react with alkenes but not carbonyl carbons.</p> Signup and view all the answers

    When are chromium agents used for oxidation and manganese agents?

    <p>Chromium in acidic conditions, manganese in basic conditions.</p> Signup and view all the answers

    What types of chromium agents partially oxidize and give examples?

    <p>Anhydrous chromium agents such as PCC; others fully oxidize.</p> Signup and view all the answers

    What is the haloform reaction?

    <p>Converting methyl ketones to carboxylic acids using a diatomic halide followed by neutralization.</p> Signup and view all the answers

    How does ozone react with alkenes?

    <p>Ozone cleaves alkenes to form ketones and aldehydes.</p> Signup and view all the answers

    What does periodic acid cleave?

    <p>Cis-1,2-diols.</p> Signup and view all the answers

    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.

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