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First Point of Difference Rule

answer

Rule that states that you number a carbon chain from the side that yields the lowest numbers for substituents

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Cracking

answer

Cleaving large hydrocarbons to yield smaller ones for petroleum

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Reforming

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Conversion of long aliphatic hydrocarbons to aromatics and branched alkanes, which tend not to knock (preignite)

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Conformers/Rotamers

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Different conformations of the same molecule

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Staggered Conformation

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Conformation in which C-H bonds are arranged such that each one bisects the angle defined by two C-H bonds on an adjacent carbon

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Eclipsed Conformation

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Conformation in which C-H bonds are arranged such that each one is aligned with the C-H bonds on an adjacent carbon

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Anti

answer

Torsion angle of 180°

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Gauche

answer

Torsion angle of 60°

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Torsion Angle

answer

Angle between C-H bonds on adjacent carbons; also known as dihedral angle

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Torsional Strain

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Destabilization associated with eclipsed bonds on adjacent atoms

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Steric Hindrance

answer

Also known as van der Waals strain; the destabilization of a molecule that results when two of its atoms are too close to each other, like the flagpole hydrogens in cyclohexane's boat conformation

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Angle Strain

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Strain that a molecule experiences because one of more of its bond angles deviate from the ideal value (usually 109.5°)

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Chair Conformation

answer

Most stable conformation of cyclohexane; nearly free of angle and torsional strain (all bonds are staggered)

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Axial

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Bonds that are parallel to an axis of symmetry that passes through a ring's center

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Equatorial

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Bonds that are located approximately at the center of the molecule of a ring

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1,3-Diaxial Repulsions

answer

Repulsions between axial substituents on the same side of a ring

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Cyclopentane

answer

Has planar, envelope, and half-chair conformations

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Spirocyclic Compounds

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Compounds that have one carbon atom common to two different rings

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Substitutive Nomenclature

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Naming that treats alkane chain as the base of the molecule (example: 1-chloropentane; butanone)

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Radicofunctional Nomenclature

answer

Naming that treats the functional group as the base of the molecule (example: pentylchloride; ethylmethylketone)

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Alkyloxonium

answer

Conjugate acid of an alcohol of general form ROH₂⁺

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Alkoxide

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Conjugate base of an alcohol of general form RO⁻

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Concerted Reaction

answer

A reaction that proceeds by way of a single elementary step

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Inductive Effect

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Electron-donating or electron-withdrawing effect of a group that is transmitted by the polarization of electrons in sigma bonds

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Hammond's Postulate

answer

The statement that if two states, such as a transition state and an intermediate derived from it, are similar in energy, then they are similar in structure

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Regioselectivity

answer

Reactions in which more than one constitutional/structural isomer can be formed from a single reactant, but in which one isomer predominates

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Vinyl

answer

Common name for the ethenyl group (CH₂=CH-)

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Allyl

answer

Common name for the propenyl group (CH₂=CHCH₂-)

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Methylene

answer

CH₂ group

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Methine

answer

CH group

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Zusammen

answer

"Together"; higher priority substituents are on the same side of the double bond

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Entgegen

answer

"Opposite"; higher priority substituents are on the opposite side of the double bond

question

Cahn Ingold Prelog Priority Rules

answer

Rules of priority for substituents used in the EZ and SR notation systems

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Zaitsev's Rule

answer

Rule stating that the alkene formed in the greatest amount by beta-elimination is the one that corresponds to the removal of the hydrogen from the carbon having the fewest hydrogen substituents

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Syn Addition

answer

Reactions in which electrophiles add to the same face of a double bond

question

Anti Addition

answer

Reactions in which electrophiles add to opposite faces of a double bond

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Stereoselectivity

answer

Reactions in which a single starting material can give two or more stereoisomeric products but in which one of them predominates

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Stereospecificity

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Reactions in which, when carried out with stereoisomeric starting materials, products are formed from one reactant that are stereoisomers of the products formed from the other reactant

question

Markovnikov's Rule

answer

Rule that states that when an unsymmetrically substituted alkene reacts with a hydrogen halide, the hydrogen adds to the carbon that has the greater number of hydrogen substituents, and the halogen adds to the carbon having fewer hydrogen substituents

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Peroxide Effect

answer

Conditions in which free radical addition of HBr to alkenes yields anti-Markovnikov products

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Principle of Microscopic Reversibility

answer

In any equilibrium process, the sequence of intermediates and transition states encountered as reactants proceed to products in one direction must also be encountered in precisely the reverse order in the opposite direction

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Hydroboration Oxidation

answer

Reaction of alkenes with boranes, and then subsequently with hydrogen peroxide and base to yield anti-Markovnikov alcohols

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Vicinal

answer

Adjective that describes substituents on adjacent carbons

question

Geminal

answer

Adjective that describes substituents on the same carbon

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Ozonolysis

answer

Reaction of alkenes with ozone to yield ozonides, which are then cleaved by water to yield two carbonyls

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Enantiomers

answer

Stereoisomers that are nonsuperimposable mirror images of each other

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Specific Rotation

answer

The quantity that describes the tendency of an enantiomer to rotate plane-polarized light

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Optical Purity

answer

Percent enantiomeric excess

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Diastereomers

answer

Stereoisomers that are not enantiomers (one stereocenter's configuration differs the other, but the second stereocenters have the same configuration, like RR and RS)

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Erythro

answer

Diastereomer in which like substituents are on the same side of the Fischer projection

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Threo

answer

Diastereomer in which like substituents are on opposite sides of the Fischer projection

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Meso

answer

A combination of stereocenters that yields this type of compound compound that is achiral (it has a plane of symmetry that passes through the molecule)

question

Resolution

answer

Separation of a racemic mixture into its enantiomeric components

question

Isotactic

answer

Polymers in which side groups are all on the same side of the polymer chain

question

Syndiotactic

answer

Polymers in which side groups are on alternating sides of the polymer chain

question

Atactic

answer

Polymers in which side groups are randomly distributed on both sides of the polymer chain

question

Inversion of Configuration

answer

Back-side attack; nucleophile attacks a substrate from the side opposite from that of the leaving group; also known as Walden _____

question

Solvolysis

answer

Substitution reactions in which the nucleophile is the solvent

question

Cyclooctyne

answer

Smallest stable cycloalkyne

question

Carbanion

answer

Conjugate base of a hydrocarbon or a compound with negatively charged carbon

question

Lindlar Catalyst

answer

Catalyst used for the semihydrogenation of alkynes to alkenes; palladium on calcium carbonate combination with PbC₂H₃O₂ and quinoline that poison the catalyst

question

Isolated

answer

Dienes in which the double bonds are separated from each other by one or more sp³ hybridized carbons

question

Conjugated

answer

Dienes in which the double bonds are connected to each other by a single bond

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Cumulated

answer

Dienes in which one carbon atom is common to two carbon-carbon double bonds

question

Allenes

answer

Cumulated dienes

question

1,2 Addition

answer

Direct addition to conjugated dienes; no allylic shift occurs

question

1,4 Addition

answer

Conjugate addition to conjugated dienes; allylic shift occurs

question

Diels Alder Reaction

answer

Conjugate addition of an alkene (dienophile) to a diene; always forms a ring

question

Pericyclic

answer

One-step reaction that proceeds through a cyclic transition state

question

Electrocyclic

answer

Reaction in which a sigma bond is formed between the ends of a conjugated π electron system (or the reverse)

question

Arenes

answer

Common name for aromatic hydrocarbons

question

Birch Reduction

answer

Dissolving metal reductions; reaction of benzene with metal to yield cyclohexadiene and the metal's cation

question

Hückel's Rule

answer

Among planar, monocyclic, fully conjugated polyenes, only those possessing (4n + 2) π electrons will have special aromatic stability

question

Annulene

answer

Completely conjugated monocyclic hydrocarbons

question

Pyridine

answer

Basic heterocyclic aromatic compound with formula C₅H₅N

question

Pyrrole

answer

Weakly basic heterocyclic aromatic compound with formula C₄H₅N

question

Furan

answer

Heterocyclic aromatic compound with formula C₄H₄O

question

Thiophene

answer

Heterocyclic aromatic compound with formula C₄H₄S

question

Electrophilic Aromatic Substitution

answer

Reaction of aromatic compounds: ArH + EY → ArE + HY

question

Cyclohexadienyl

answer

Also known as the arenium ion, of form C₆H₆E⁺ where E is an electrophile

question

Friedel Crafts Reaction

answer

Synthetic method of alkylation of benzene from an alkyl halide in the presence of a Lewis acid, such as AlCl₃ or FeBr₃

question

Grignard Reagents

answer

Organometallic reagents of form RMgX, useful in the preparation of alcohols

question

Retrosynthetic Analysis

answer

Method of synthesis in which one reasons backwards from the target molecule to suitable starting materials, championed by E. J. Corey

question

Gilman Reagents

answer

Organometallic reagents of form R₂CuLi, useful in synthesizing large organic molecules

question

Simmons Smith Reaction

answer

Synthetic reaction for the preparation of cyclopropanes from alkenes using iodomethylzinc iodide (ICH₂ZnI)

question

Carbene

answer

Neutral molecules in which one of the carbon atoms has six valence electrons (two bonds and one lone pair)

question

Carbenoids

answer

Molecules that behave like carbenes in chemical reactions

question

Oxymercuration Demercuration

answer

Conversion of alkenes to alcohols using mercury (II) acetate by way of β-hydroxyalkylmercury (II) acetate

question

Hydroxylation

answer

Addition of two hydroxyl groups to a double bond forming a diol, such as the reaction of alkenes with osmium tetraoxide (OsO₄)

question

Fischer Esterification

answer

Acid-catalyzed condensation of an alcohol and a carboxylic acid

question

Mercapto

answer

Formal name for the sulfhydryl group (known as thiol when it is the main functional group), -SH

question

Disulfides

answer

Name for the functional group R-S-S-R

question

Alkoxy

answer

Substitutive name for the ether functional group, R-O-R

question

Crown Ethers

answer

Macrocyclic polyethers, cyclic compounds containing 4 or more ether linkages in a ring of 12 or more atoms; useful for dissolving ions in nonpolar solvents

question

Williamson Ether Synthesis

answer

Synthesis of ethers by the nucleophilic substitution of an alkyl halide by an alkoxide anion

question

Sulfone

answer

Functional group containing the unit R-SO₂-R

question

Sulfonium

answer

Ions of the general form R₃S⁺

question

Hydroformylation

answer

Reaction converting alkenes to aldehydes containing an additional carbon atom; reacted with CO and H₂ in the presence of a cobalt or rhodium based catalyst

question

Cyanohydrin

answer

Compounds containing cyano and hydroxyl groups bonded to the same carbon

question

Hemiacetal

answer

Compound containing a hydroxyl group and an ether bonded to the same carbon

question

Acetal

answer

Compound containing geminal ether groups (geminal diethers), prepared by the treatment of aldehydes with alcohols

question

Carbinolamine

answer

Compound containing a hydroxyl group and an amine group on the same carbon

question

Imine

answer

Compound containing a carbon double bonded to a nitrogen (R₂C=NR)

question

Enamine

answer

Compound containing a carbon double bonded to another carbon and single bonded to an amine group (R₂C=CR(NR₂))

question

Wittig Reaction

answer

Synthesis of alkenes from the reaction of aldehydes or ketones with phosphorus ylides

question

Ylide

answer

Neutral molecules that have two oppositely charge atoms, each with an octet of electrons, directly bonded to each other

question

Baeyer-Villiger Oxidation

answer

Reaction of ketones and peroxy acids to yield esters and carboxylic acids

question

Enolate

answer

Conjugate base of a carbonyl compound (R₂C=CRO⁻)

question

Aldol Addition

answer

Reaction of two aldehydes to yield a compound containing both an aldehyde functional group and a hydroxyl group

question

Aldol Condensation

answer

Reaction of aldol addition followed by an elimination reaction, yield α,β-unsaturated aldehydes and water

question

Nucleophilic Substitution

answer

Reaction of the form Nu + R₃C(Lg) → NuCR₃ + Lg

question

Lipophilic

answer

Fat-loving

question

Nitriles

answer

Alkyl cyanides, of the form RCN

question

Decarboxylation

answer

Reaction of carboxylic acids to yield alkanes and carbon dioxide

question

Carboxamides

answer

Name for acyl amines

question

Lactones

answer

Cyclic esters

question

Lactams

answer

Cyclic Amides

question

Imide

answer

Two acyl groups bonded to a single nitrogen

question

Carbamic Acid

answer

Carboxylic acids in which the R group is an amine

question

Aniline

answer

Amino-substituted derivatives of benzene

question

Kolbe Synthesis

answer

Reaction of sodium phenoxide with carbon dioxide to yield salicylic acid

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