Download Chapter 9

Chapter 9
Organic Chemistry
Some Definitions
•
•
•
•
•
•
•
•
Hydrocarbon
Saturated hydrocarbon
Unsaturated hydrocarbon
Cyclic hydrocarbon
Structural formula
Condensed structural formula
Isomer
Functional Group
General Uses of Hydrocarbons
• Halogenated
Teflon: polytetrafluoroethane (PTFE)
– CFCs
– Teflon
– Perfluoro
•
•
•
•
Solvents
Anesthetics
Perfumes, flavorings
Building blocks of the
body
Source: http://www.worldofmolecules.com/pesticides/ddt.htm
Alkanes
• Hydrocarbons that contain
only single bonds
• General formula CnH2n+2
• Named from the number of
carbons
• Can have isomers
• Can be cyclic (different
formula)
Properties of Alkanes
• State of matter
– Less than 5 carbons = gas
– Between 5 and 16 carbons = liquid
– Greater than 16 carbons = solid
• Non-polar molecules (insoluble in water)
• Very flammable: used for combustion
• Physiological effects: dissolve fats, can
act as emollients
Functional Groups
• Any variation on the single carbon chain
• Hydrocarbon stem called an alkyl group
• Additions of bonds, halogens, oxygen or
nitrogen
– Alkene
– Alkyne
– Alcohol
– Carboxylic Acid
– Ester
– Amine
– Amide
Functional Groups
Alkenes
• Hydrocarbons that contain at
least one double bond
• General formula CnH2n
• Named from the number of
carbons
• Can be cyclic
– Aromatic hydrocarbons:
benzene
Alkynes
• Hydrocarbons that contain at
least one triple bond
• General formula CnH2n-2
• Named from the number of
carbons
Properties of Alkenes & Alkynes
• State of matter
– Contain 2-4 carbons = gas
– Contain 5-18 carbons = liquid
– Greater than 18 carbons = solid
• Non-polar molecules
(insoluble in water)
DDT
• Flammable
• Undergo saturation and addition reactions
• Physiological effects: unsaturated fats,
aromatics act as narcotics, many toxic (DDT,
phosgene)
Source: http://www.worldofmolecules.com/pesticides/ddt.htm
Alcohols
• Alkanes that contain an –OH substituted
for any hydrogen
– Called a hydroxyl functional group
• Named according to number of carbons
in alkyl group
• -e on alkane name changes to -ol
Properties of Alcohols
• State of matter
– Liquid
• Soluble in water
• Formed by fermentation or
catalyzed chemical reactions
• Many are toxic!
• Other common alcohols:
Source: http://www.worldofmolecules.com/pesticides/ddt.htm
– Propylene glycol: antifreeze
– Glycerol: moisturizer, food
additive for moisture
Source: http://www.sonarestaurant.com/wine.php
Carboxylic Acids
• Called a carboxyl group
• May see it written as --COOH
• Named from the number of carbons + “oic acid”
– Methanoic acid (in ant and bee stings)
– Ethanoic acid (acetic acid in vinegar)
– Propanoic acid
– Butanoic acid (rancid butter, body odor)
Properties of Carboxylic Acids
• Weak acids
• Sour taste, neutralize
base
• Produce H+ ions in water
• Carboxylic acid salts =
used as anti-mold food
additives
Esters
• Contain a carbon double-bonded to one
oxygen, single bonded to another
• Named according to number of carbons
• 2 words, end in –ate
Source: http://www.iff.com/Ingredients.nsf/0/73944D7BC97392548525699F006C522B
Methyl Butyrate
Source: http://leonlab.bio.uci.edu/images/2D/ethylbutyrate.gif
Ethyl Butyrate
Properties of Esters
• Formed by combination of an
alcohol and an acid
• Some soluble in water, some
insoluble
• Fragrant: used in foods and
perfumes
– Many fruity
• Other important esters:
– Salicylic acid
• Antipyretic
• Analgesic
• Blood thinner
Source: http://www.worldofmolecules.com/pesticides/ddt.htm
Amines
• Contain at least one –N group
– Called an amino functional group
• Named according to number of carbons attached
to the amino
– Names depend on where amino is in chain
• Name examples:
–
–
–
–
–
–
CH3NH2 = methylamine
CH3CH2NH2 = ethylamine
CH3NHCH3 = dimethylamine
CH3CH2CH2NH2 = propylamine
CH3NHCH2CH3 = methylethylamine
CH3CH2NHCH3 = ethylmethylamine
Properties of Amines
• Formed from ammonia by replacing
hydrogens with alkyl groups
• Soluble in water (low MW)
• Many are toxic & carcinogenic
• Unpleasant odors
• Act as weak bases
• Biological importance
– Amino acids
– Proteins
– Drugs
Source: http://www.worldofmolecules.com/pesticides/ddt.htm
Adrenaline
Complex Amines: Heterocyclic
• Carbon rings with nitrogens replacing
carbons
• Hetero = not evenly spaced
Source: http://www.worldofmolecules.com/pesticides/ddt.htm
Purine
Pyrimidine
Amides
• Contain a carbon double-bonded to oxygen,
single bonded to nitrogen
• Soluble in water (low MW)
• High boiling points and melting points
• Most (more than 1 carbon) are solid at room
temperature
• Most important amides are complex
– Proteins
– Nylon, wool, silk
Source: http://www.worldofmolecules.com/pesticides/ddt.htm
Nylon = hydrocarbons with amide linkages
Try It!
H
•
•
•
•
H
H
H
C
C
C
H
H
H
Category?
Properties?
Are isomers possible?
Name?
H
Try It!
H
• Category?
• Properties?
H
H
C
C
N
H
H
H
H
Try It!
H
H
O
C
C
H
• Category?
• Properties?
• Name?
O
H
Of our 8 molecule types, can you…
• Name the 3 types of hydrocarbons?
• Name the hydrocarbon with a triple bond?
• Name the molecules that include any double
bonds?
• Name the molecules that include any
nitrogens?
• Name the molecules that include any oxygens?
• Name the molecules that are soluble in water?
• Name the molecules that are insoluble in
water?
Practice
1. Which of the molecules below:
– Are soluble in water?
– Are saturated hydrocarbons?
– Are isomers of each other?
2. Name each molecule.
Practice
3. Draw a molecule that contains 4 carbons
single bonded to each other, and one
amine group. Hydrogens make up the
rest of the bonds.
– Name 2 physical properties of this
molecule.
4. Draw a molecule of propene.
– Name 3 physical properties of this
molecule.
Practice
5. Which of the molecules
below:
– Are insoluble in water?
– Are unsaturated
hydrocarbons?
– Are hydrocarbons that are
liquid at room temperature?
Practice
6. Draw a molecule that contains 5 carbons
single-bonded to each other and one
hydroxyl group. Hydrogens make up the
rest of the bonds.
– Name this molecule
– Name 2 physical properties of this
molecule.
7. Draw a molecule of pentyne.
– Name 3 physical properties of this
molecule.
Practice
6. Draw a molecule that contains 5 carbons
and one ester group. Hydrogens make
up the rest of the bonds.
– Name 2 physical properties of this
molecule.
7. Draw a molecule of pentyne.
– Name 3 physical properties of this
molecule.
8. Write the molecular formula and name of
an alkene that contains 18 hydrogens.
Practice
H
H
H
C
C
H
H
O
OH
H
H
C
O
C
H
H
H
H
H
C
C
C
H
H
H
H
A
C
B
C
H
D
H
H
H
H
H
C
C
C
C
H
H
H
H
H
H
H
O
C
C
H
E
H
N
H
H
H