Quicksheet: Organic Chemistry

carboxylic acid

prefix: carobxy-

suffix: -oic acid

anhydrides

previx: alkanoyloxy- ; carbonyl-

suffix: anhydride

esters

prefix: alkoxycarbonyl-

suffix: -oate

amides

prefix: carbomoyl-

suffix: -amide

aldehydes

prefix: oxo-

suffix: -al

ketones

prefix: oxo-; keto-

suffix: -one

alcohols

prefix: hydroxy-

suffix: -ol

nucleophile

-“nucleus-loving”

-usually lone pairs or pi bonds that can form new bonds to electrophiles

• inc. by increasing electron density

how is nucleophilicity determined

-charge: increases with increasing electron density (more neg charge)

-electronegativity: decreases as electroneg increases b/c these atoms are less likely to chare electron density

-steric hindrance: bulkier molecules are less nucleophillic

-solvent: protic solvents can inhibit nucleophilicity by protonating the nucleophile or through H-bonding

nucleophilicity in aprotic vs protic solvents

-nucleophilicity is parallel bacicity: F>Cl>Br>I

-nucleophilicity is antiparallel: I>Br>Cl>F

electrophile

-“electron loving”;

-usually positive charge or positively polarized atom that accepts an electron pair from a nucleophile

-inc. by increasing the positive charge

most common electrophiles

carbonyl carbon

substrate carbon in an alkane

carbocations

leaving group

-retain the electrons after heterolysis (breaking a bond with both electrons being given to one of the two protons)

-best will be able to stabilize the extra elections

most common leaving groups

weak bases

large groups with resonance

large groups with electron-w/drawing atoms

physical properties

processes that don’t change the composition of matter

• melting point, boiling point, solubility, odor, colo, density

chemical properties

reactivity of the molecule with other molecules

angle strain

stretch or compress angles from normal size

torsinal stran

from eclipsing confomations

nonbonded strain

from interactions with substituents on nonadjacent carbons

• cyclohexane - largest substituent usually takes equatorial position to reduce nonbonded strain

configurational isomers

can only be interchanged by breaking and reforming bonds

• enantiomers, diastereomers, cis-trans

enantiomers

-nonsuperimposable mirror images

-opposite stereochemistry at every chiral carbon

-same chemical and physical properties except for rotation of plane-polarized light and rxns in a chiral environment

• racemic mixtures and meso compounds are optically inactive

Diastereomers

non-mirror image stereoisomers; differ at some, but not all, chiral centers; different chemical and physical properties

Cis-Trans

subtype of diastereomers in which groups differ in position about an immovable bond (such a double bond or in a cycloalkane)

cis-trans

subtype of diastereomers in which groups differ in position about a immovable bond (such as a double bond or ina cycloalkane)

alcohols

• higher boiling points than alkanes due to hydrogen bonding

  • weakly acidic hydroxyl hydrogen

synthesis of alcohols

• addition of water or double bonds

• Sn1 and Sn2 rxns

• reduction of carboxylic acids, aldehydes, ketones, and esters

  • aldehydes and ketones with NaBH4 or LiAlH4

  • esters and carboxylic acids with LiAlH4

oxidation

loss of electrons, fewer bonds to hydrogens, more bonds to heteroatoms (O,N, halogens)

Reduction

gain of electrons, more bonds to hydrogens, fewer bonds of heteroatoms

ubiquinone

also called coenzyme Q and is a vital electron carrier associated with Complexes I, II, and IIII of the elctron transport chain

chromatography

uses a stationary phase and a mobile phase to separate compounds based on polarity and/or size