Organic and Biological Molecules
Chapter 22
Organic chemistry is difficult. Those who study it have alkynes of troubles.
Ha! Ha! Ha! What a joke. Amine that is really funny!
Hydrocarbon Derivatives
Functional groups – additional atoms or groups added to hydrocarbons
Alcohols -OH replace the –e in the name with -ol
Hydrocarbon Derivatives - Alcohols
Classified by number of hydrocarbon fragments (R)
Primary
R
CH2OH
R
Secondary
CHOH
R’
R
Tertiary
R’
C OH
R”
Hydrocarbon Derivatives - Alcohols
Higher boiling points than molecules of similar molar mass
C
O
H
65 C
32 g/mol
Hydrogen Bonds
C
C
-89 C
30 g/mol
London Dispersion
Hydrocarbon Derivatives - Alcohols
Methanol = wood alcohol
CO + 2H2
400 C
ZnO / Cr2O3
CH3OH
Used as starting material for many products
Toxic – causes blindness
hydrogenation of CO
Hydrocarbon Derivatives - Alcohols
Ethanol = grain alcohol
C6H12O6
yeast
CH3 CH2 OH + 2 CO2
Only proceeds until alcohol content is 13%
Then yeast can’t survive
Higher % is achieved through distillation
Commercial production
C
C
+
H2O
acid
catalyst
C
C
O
H
Hydrocarbon Derivatives - Alcohols
Try naming
CH3CH CH2 CH3
OH
Cl CH2 CH2 CH2 OH
Br
OH
Hydrocarbon Derivatives – Aldehydes
Carbonyl group
C
O
Aldehydes
Naming: remove –e, add –al
the aldehyde carbonyl is always #1
O
C
R
H
Aldehydes have strong odors
Formaldehyde
cinnamaldehyde
vanillin
butraldehyde
Hydrocarbon Derivatives – Ketones
Carbonyl group
C
O
Ketones
Naming: remove –e, add –one
the number indicates the
position of the carbonyl
O
C
R
R
Useful solvent properties such as acetone
2-propanone
dimethylketone
Hydrocarbon Derivatives – Aldehydes and Ketones
Production of aldehydes and ketones
Oxidation of alcohols
primary alcohols produce aldehydes
O
CH3 CH2 OH
CH3
H
secondary alcohols produce ketones
CH3 CH CH3
CH3 C CH3
OH
O
Hydrocarbon Derivatives – Aldehydes and Ketones
Hydrocarbon Derivatives – Carboxylic Acids
O
Carboxyl group
C
R-COOH
weak acids
OH
Naming: drop the –e, add –oic acid
CH3 COOH ethanoic acid (acetic acid)
C
O
Production – oxidation of primary alcohol
CH3CH2OH
KMnO4
CH3COOH
Hydrocarbon Derivatives – Esters
O
Carboxyl group
R
sweet, fruity odors
C
O-R
Naming: change the –oic acid of the parent acid to –oate
parent alcohol chain is named first
Production – carboxylic acid reacts with an alcohol
H-O
H
ethanoic acid
ethanol
n-ethylethanate
Hydrocarbon Derivatives – Esters Examples
Banana scent
n-amyl acetate
Orange scent
n-octyl acetate
Aspirin
Salicylic acid
acetic acid
acetylsalicylic acid
Hydrocarbon Derivatives – Amines
Derivatives of ammonia N-H is replaced with N-C
Primary
Secondary
:
H
:
:
C
N
Tertiary
H
C
N
C
H
Common names are often used for simple amines
NH2
CH3 CH CH2 CH3
amino
2-amino butane
NH2
Fish-like odors
associated with decaying animal tissue
putrescine H2N(CH2)3NH2
cadaverine H2N(CH2)5NH2
Used to make dyes
Some are carcinogenic
C
N
C
C
Hydrocarbon Derivatives – Amines