Organic Chem 1 Flashcards
Major functional groups - Polar or Hydrophlic
- alcohols - amines - carbonyl derivatives all soluble in water
Major functional groups - Nonpolar or Hydrophobic Groups
- alkyls - aromatics all soluble in oil
Alcohols
- contain hydroxyl groups bound to carbons - are polar because the oxygen has two pairs of non-bonded electrons.
Hydroxyls suffix
- OH
Primary Alcohol
RCH2OH ie: ethanyl alcohol CH3CH2OH
Secondary Alcohol
R2CHOH isopropyl alcohol (CH3)2CHOH
Tertiary Alcohol
R3COH tertiary butyl alcohol (CH3)3COH
Quaternary Alcohol
doesn’t exist :)
Properties of Alcohols
- can give up a proton - not acidic - only ionize under strong basic conditions (ie: propofol pKa of 11 poorly ionizes)
If the alcohol contains electron withdrawing groups it will ______
become more acidic ie: (CF3)2CHOH is more acidic than (CH3)2CHOH hexafluoroisopropanol is more acidic than isopropanol because of the highly electronegative fluorine substituents
Types of Amines: Primary
RNH2 (one group)
Types of Amines: Secondary
R2NH2 (two groups)
Types of Amines: Tertiary
R3N (three groups)
Types of Amines: quaternary ammonium ion
R4N+
Cyclic amines can be ____
secondary, tertiary, or quaternary
Amines are derivatives of ammonia
Examples: NH3 - ammonia CH3NH2 - methylamine CH3NHCH3 - dimethylamine CH3N(CH3)CH3 - trimethalamine
Amines have a lone pair of _______ electrons on the nitrogen atom
non-bonded
Cation
nitrogen with four substituents
pKa of amines
basic with a pKa of 8-11
Properties of Alkyl Functional Groups
1. Nonpolar (or lipophilic). electrons are more equally shared between atoms, no unbound outer shell electrons, atoms not charged
2. Poorly miscible in water (or aqueous phases). The addition of these groups to a molecule will decrease water solubility of a molecule.
Hydrocarbon
molecule contains only hydrogen and carbon
Alkyl functional groups
saturated, non-aromatic hydrocarbon groups.
Common alkyl groups:
“n”
“n” = normal. It means a straight hydrocarbon chain, no branching
“iso”
“Iso” = same. It means a branched hydrocarbon chain having branches that are the same.
Prefixes that designate the numbers of carbons:
Meth = 1
eth = 2
prop = 3
but = 4
pent = 5
oct = 6
Major polar groups
Why are the major polar groups “polar”?
These groups are polar because of the unbound electrons on the oxygen atom which allows interactions with water and other polar groups
Polarity and ionization of functional groups have major effects on the behavior of molecules…
Not all polar groups readily ionize, but they are hydrophilic because the groups are polar. For example, hydroxyls, ethers, esters and amides poorly ionize.
Carboxylic acids
tend to give up a proton and become ionized and in doing so
become ionized
Amines are basic and
tend to acquire a proton and in doing so they become ionized
Carboxylic acids and amines can both
readily ionize
Fatty acids
combine the extremes of lipophilicity and hydrophilicity in the same molecule - ie, a long alkyl side chain and a highly polar carboxylic acid group on one end.
They have the property of soaps
saturated
hydrocarbon molecule containing only single carbon-carbon bonds
unsaturated
hydrocarbon molecules containing double or triple carbon-carbon bonds
conjugated
denotes alternations of double-single bonds
ene
denotes a double bond
