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37 Cards in this Set

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Tautomers
Isomers that can interconvert by exchanging the location of a proton.
Enolization
The process by which the carbonyl oxygen of a ketone gets protonated to form an enol.
Oxidation of Alcohols
Primary alcohols can be oxidized to aldehyde's using PCC and further oxidized to carboxylic acids using KMnO4, NA2CR2O7, or Cr03.

Secondary alcohols can be oxidized to ketones using any of these oxidants.
Resonance
Describes a situation where the atomic connectivity remains unchanged while the electron distribution between the atoms changes.
Phenyl
The term used to describe benzene when it is used as a substituent.
Huckel's Rule
The rule stating that in order for a ring to be aromatic, it must contain 4n+2 conjugated π electrons.
Deactivating Substituents
Deactivating subsituents are electron-withdrawing subsitutents already attached to the aromatic ring.

They decrease the ring's potential to react with other species.

With the exception of halogens (which are ortho/para directing), deactivating species are meta directing.
Benzyl
The term used to describe toluene substituted at the methyl position when it is used as a substituent.
Aromatic Compound
Cyclic, fully conjugated planar compound with 4n+2π electrons.

Each atom in the compound must possess a p orbital in order to allow for maximum conjugation.
Activating Substituents
Electron-donating substituents already attached to the aromatic ring.

They increase the ring's potential to react with other species.

Activating species are ortho/para directing
Sn2 Reactions
Bimolecular nucleophilic substitution reactions occur through a concerted mechanism where the nucleophile attacks as the leaving group starts to leave.

Reactivity increases from tertiary to secondary to primary with decreasing steric effects.
Sn1 Reactions
Unimolecular nucleophilic substitution reactions. The leaving group leaves, forming a carbocation that then reacts with a nucleophile.

Reactivity increases from methyl to primary to secondary to tertiary with increasing carbocation stability.
Nucleophile
A species that tends to donate electrons to another atom.

Nucleophiles are attracted to positive charge. For nucleophiles with the same attacking atom (-OH-, CH3O-) in a protic solvents, nucleophile strength correlates to basicity.

In protic solvents and in situations where the attacking atom is different (OH-, SH-), nucleophile strength correlates to size.
Leaving Group
Atoms that can dissociate to form a stable species after accepting electron pairs.

Weak bases tend to be good leaving groups.
Secondary Carbon
A carbon atom bonded to two other carbon atoms.
Alpha Carbon
Carbon adjacent to the carbon containing the functionality under consideration.
Sterioisomers
Compounds with the same molecular formula and connectivity but different arrangements in space.

Include geometric isomers, diastereomers, enantiomers, conformational isomers, and meso compounds.
Racemic Mixture
A mixture that contains equal amounts of the (+) and (-) enantiomers.

Are not optically active.
Structural Isomers
Compounds with the same molecular formula but different connectivity.

Have different chemical and physical properties.
Meso Compound
A stereoisomer with an internal plane of symmetry.

Optically inactive.
Geometric Isomers
Isomers that differ in the arrangement of substituents around a double bond.

Are often differentiated using either the cis/trans notation for simple compounds or Z/E for more complex compounds.

Can differ in their physical and chemical properties.
Enantiomers
Nonsuperimposable stereoisomers that are mirror images of each other.

Differ in configuration at every chiral center but share the same chemical and physical properties in a nonstereospecific environment.

Optical activity is different.
Diastereomers
Sterioisomers that are not mirror images of each other.

They differ in their configurations in at least one chiral center and share the same configuration in at least one chiral center.

They have the same chemical properties but different physical properties.
Conformational Isomer
Stereoisomers that differ by rotation about one or more single bonds, usually represented using Newman projections.
Chiral Molecule
A molecule that is not superimposable upon its mirror image.

It must have at least one central atom attached to four different atoms.

A molecule with multiple chiral centers can be achiral (ie meso compound)
Ketone
A compound that has a nonterminal carbonyl group.

They are named by replacing the -e in the corresponding alkane with -one.
Imine
A compound that has carbon double bonded to nitrogen
Haloalkanes
Alkanes with a halogen substituent.

The compound can be named either as a haloalkane or as an alkyl halide
Ether
A compound that has an oxygen attached to two alkyl groups (R-O-R').

The compound can be named either as an alkoxyalkane or as an alkyl ether.
Ester
A compound that has a COOR group.

Named as alkyl or aryl alkanoates.
Carboxylic Acid
A compound that has an COOH terminal group.

Named by replacing the -e with -oic acid.

Formic acid and acetic acid are common names for the simplest acids: methanoic acid and ethanoic acid, respectively.
Amine
A compound in which a carbon atom is bonded to a nitrogen atom with a single bond.

They are named by replacing the -e in the corresponding alkane with -amine.

Substituent groups attached to the nitrogen can be named using the prefix N-.
Amide
A compound that has a carbonyl gruop bonded to nitrogen.

They are named by dropping the -oic acid and adding -amide.

Substituents attached to the nitrogen are listed following N-.
Alkynes
Compounds containing carbon-carbon triple bonds.

The compound is named by replacing the -ane in the corresponding alkane with -yne.
Alkenes
Compounds containing carbon-carbon double bonds.

The compound is named by replacing the -ane in the corresponding alkane with -ene.
Alkanes
Compounds consisting of only carbons and hydrogens bonded with sigma bonds.

As chain length increases, boiling point, melting point and density increase.

Chain branching decreases both boiling point and density.
Aldehyde
A compound that has a HC=O as a terminal group.

They are named by replacing the -e with -al.