MCAT organic chemistry 1-4

1. carboxylic acid

2. anhydride

3. ester

4. amide

5. aldehyde

6. ketone

7. alcohol

8. alkene or alkyne

9. alkane

functional group priority groups

alkane

ane

Alkene

ene

alkyne

yne

alcohol

-ol

hydroxy-

aldehyde

-al

oxo-

ketone

-one

oxo-

amide

ester

-oate

alkoxycarbonyl-

annhydride

reactive toward nucleophiles

carboxylic acid

-oic acid

carboxy-

structural, conformational, configurational, enantiomers, diastereomers, cis/trans

isomers

differ around a rotation on a sigma bond

conformational isomers

have to make/break bonds

configurational isomers

equatorial bond

a bond to a chair conformation of cyclohexane that extends from the ring roughly perpendicular to the imaginary axis through the center of the ring; a bond that lies roughly along the equator of the ring

axial bond

a bond of the chair conformer of cyclohexane that points directly up or directly down

relative configuration

gives the stereochemistry of a compound in comparison to another molecule

absolute configuration

-determined by the 3D arrangement of the groups attached to the chiral carbon

t-butyl

isopropyl

neopentyl

isobutyl

sec-butyl

bronstead-lowry acid

proton donor

bronstead lowry base

proton acceptor

lewis acid

electron acceptor

lewis base

electron pair donor

pKa = -logKa

pKa equation

high pKa

weak acid, strong base

low pKa

strong acid and weak base

Alkane, alkene, hydrogen, alkyne, ester, ketone/aldehyde, alcohols, carboxylic acid, hydronium ion

weak to strong acids

determined by 4 factors : charge, electronegativity, steric hinderance, solvent

Nucleophilicity

anions, lone pairs and pi bonds

nucleophiles have

protic solvents

water, methanol, ethanol, ammonia, acetic acid

aprotic solvent

one that cannot donate protons (hydrogen ions) in an acid-base reaction

examples of aprotic solvents

DMF, DMSO, acetone

nucleophilicity increases down periodic table

trends in protic solvent

Electrophile

electron pair acceptor

leaving group

Atom or group that departs during a reaction.

carbonyl carbon

common reactive site

oxidation

increase in oxygen bonds, decrease in hydrogen bonding

Primary alcohol to aldehyde

PCC

primary alcohol to carboxylic acid

H2CrO4