Why Study Organic Chemistry?
What drug has
the worst
withdrawal
most abused symptoms?
What substance is considered the
What is the
most addictive?
What percentage of North
Americans use caffeine
everyday?
drug?
What is the most
used drug
worldwide?
What class of drug is
responsible for the most
reported poisonings of
any substance?
What class of drug is the
most commonly prescribed?
What is the original source for the drugs
Vicodin, Percocet, Oxycodone, Oxycontin,
and Percodan?
What is the
What percentage
most
of Americans takes consumed
at least one
psychoactive
prescription drug
substance in
daily?
the world?
Why Study Organic Chemistry?
Nicotine
Caffiene
90%
Opium poppy
Alcohol,
followed by
benzodiazapines
and then opiates
Marijuana
Opioid
analgesics such
Nearly 70%
as morphine,
hydrocodone, Lipid regulators,
oxycodone,
followed by
methadone
antidepressants
and then narcotic
analgesics
Caffiene
How Important is Organic Chemistry
in Daily Life?
What is the
What is the starting
material used to
produce most
pharmaceuticals?
What is
the most
recycled
material
in the
United
States?
What class of drug is
responsible for the most
poisoning deaths of any
substance?
What is the most
explosive non-nuclear
substance?
What is the strongest
substance known?
most toxic
substance
known?
Where does
asphalt come from
(and basketballs,
lipstick, contact
lenses, nylon)?
What is the world’s most
abundant organic
compound?
How Important is Organic Chemistry
Botulinum toxin is a
in Daily Life?
protein and
neurotoxin produced
Of accidental deaths in the US, by the bacterium
poisoning is the #1 cause; 89% Clostridium
botulinum
Petroleum
http://www.petroleum.co.uk/
other-uses-of-petroleum
Asphalt, steel, and
automotive lead
batteries, depending
on how it’s measured
of poisoning deaths were due
to drugs, and 77% of these
deaths were unintentional;
opioid analgesics account for
40% of these deaths
OCTANITOCUBANE
http://news.softpedia.com/news/The-MostPowerful-Non-nuclear-Explosives-in-the-World58104.shtml
Carbyne
http://cleantechnica.com/2013
/10/10/carbyne-strongestmaterial-yet-known-possessesnumber-useful-propertiesresearch-finds/
http://io9.com/5861680/10of-the-most-dangerouschemicals-in-the-world
http://someinterestingfacts.n
et/top-10-most-deadliestsubstance-known-to-man/
Petroleum
http://whgbetc.com/petroproducts.pdf
Cellulose
Types of Organic Compounds
• Vast majority of over 20 million known
compounds are based on C: organic
compounds.
• Generally contain C and H + other elements
• Great variety of compounds
Hydrocarbons
• Compounds of C and H
• Subgroups:
–Alkanes: C-C single bonds
–Alkenes: C=C double bonds
–Alkynes: carbon-carbon triple bonds
–Aromatic: based on benzene
Hydrocarbons
•
•
•
•
•
•
Alkanes have the general formula CnH2n+2
CH4 = methane
C2H6 = ethane
C3H8 = propane
C4H10 = butane
C5H12 = pentane
Hydrocarbons: Alkanes
Alkanes are colorless gases, liquids, and
solids
Generally unreactive (but undergo
combustion)
Not polar (or low polarity) and so are not
soluble in water.
• HOW TO NAME THEM (refer to equations
book)….
CH3CH2 CH2CH2 CH3
Pentane
Hydrocarbons
& Structural
Isomerism
CH3
CH3CHCH2CH3
2-Methylbutane
CH3
H3CCCH3
CH3
2,2-Dimethylpropane
Note names of isomers
Isomers of C5H12?
C4H10 has 2 strucural
isomers
C5H12 has 3
C6H14 has 5
C7H14 has 9
C8H18 has 18
Isomerism
• Isomers have identical composition but
different structures
• Two forms of isomerism
– Constitutional or structural
– Stereoisomerism or geometric
• Structural
– Same empirical formula but different atom-toatom connections
• Geometric
– Same atom-to-atom connections but different
arrangement in space.
Structural Isomers
Stereoisomers: Geometric
Geometric isomers can occur when there is a
C=C double bond.
Cis-2-butene
Trans-2-butene
Alkenes: Compounds with C=C
Double Bonds
• How many isomers are possible for a
compound with the formula C4H8?
3 4
CH2CH3
H
1
C
H
1
C
2
C
H
H
1-butene
3
CH3
H
1
H 3C
2
C
4
CH3
2
C
CH3
2-methylpropene
(isobutene)
H
4
CH3
H
3
C
2
C
H
cis-2-butene
1
H3 C
3
C
H
trans-2-butene
Alkenes—
Many Occur Naturally
Reactions of Alkenes:
ADDITION REACTIONS
• Alkenes are unsaturated — more
bonds can form to the C atoms
• Molecules such as Br2, H2, HCl, HBr, and
H2O add to the double bond
H
C C + Br2
H
H
H
Br Br
H C C H
H H
1,2-dibromoethane
An Addition Reaction
Fat placed in Br2
vapor
• The fat in bacon is partially unsaturated.
The fat adds Br2 to the C=C bonds.
• Fats can be “hydrogenated” with H2.
An Addition Reaction
• Fats can be “hydrogenated” with H2.
Peanut butter has partially hydrogenated
vegetable oil.
CH3(CH2)7CH=CH(CH2)7CO2H
Trans Fatty Acids
tend to raise total blood
cholesterol
Alkynes
• Alkynes have carbon-carbon triple bonds.
• C2H2: common name = acetylene
systematic name = ethyne
Preparation:
CaC2(s) + H2O(liq) -->
C2H2 (g) + Ca(OH)2(s)
∆Hfo(C2H2, g) = +226.7 kJ/mol
∆Hrxn for C2H2 + O2
= –1300 kJ/mol
Aromatic Compounds
• Benzene, C6H6, in the
top 25 chemicals
produced in the U.S.
• Starting point for
hundreds of other
compounds.
Resonance in Benzene
• C6H6 has two resonance structures with alternating
double bonds.
• The π electrons are delocalized over the ring.
Resonance in Benzene
• C–C single bond = 154 pm
C=C bond = 134 pm
• CC bonds in benzene = 139 pm
π electrons delocalized
Functional Groups
Alcohols
• Characterized by –OH group
• Name: add –ol to name of hydrocarbon
Methanol
Butanol
Structures of Alcohols
C3H5OH: how many structural isomers?
H
H
H
H
C
C
C
H
H
H
1-propanol
OH
H
H
OH H
C
C
C
H
H
H
H
2-propanol
Naming: Add -ol to name of 3-C hydrocarbon. Indicate position of OH with number.
Alcohol Properties
• Alcohols are a derivative of water
• Many alcohols dissolve in water
Methanol dissolves in
water.
Butanol is NOT soluble in water.
GLYCOLS
Alcohols with Two OH Groups
Ethylene
glycol
Propylene
glycol
Amines
Alcohols are derivatives of H2O (R–OH) and
amines are derivatives of NH3.
Methylamine
Dimethylamine
Trimethylamine
Amines
Amines generally have terrible odors!
Cadaverine
Pyridine
Amines
Amines, like NH3, are bases
Amines
Many natural
products and
drugs (such as
nicotine and
cocaine) are
bases.
H+
Nicotine
O
C
Aldehyde
Compounds with
Carbonyl Group
Carboxylic acid
Ketone
Structures of Aldehydes
Cinnamaldehyde
Odors from aldehydes and
ketones
Carboxylic Acids
Acetic acid
Acids are found in
many natural
substances: bread,
fruits, milk, wine
Benzoic acid
Carboxylic acid group
with acidic H+
All are WEAK acids
Carboxylic Acids
H
O
O
C
O
Formic acid,
HCO2H, gives the
sting to ants.
C
CH3
O
Aspirin, acetylsalicylic acid
Acids + Alcohols --> ESTERS
Esters have generally pleasant odors
Acids + Alcohols --> ESTERS
3-methylbutanol
Acetic acid
O
H3C
C
CH3
O
CH2 CH2CHCH3
3-methylbutylacetate
Many fruits such as
bananas and strawberries
contain esters.
H2C
HC
H2C
O
O CR
O
O CR
O
O CR
Fats and Oils
Fats with C=C bonds are usually LIQUiDS
Oleic acid: a
monounsaturated
fatty acid
C=C bond
H2C
HC
H2C
O
O CR
O
O CR
O
O CR
Fats and Oils
Fats with saturated acids (no C=C bonds) are
SOLIDS.
Saturated fats are
more common in
animals.
Fats and Oils: Saponification
Glyceryl stearate, a fat + NaOH
O
CH2 O CR
O
+ 3 NaOH
O CR
CH
O
CH2 O CR
R = —(CH2 )16CH3
CH2 O—H
CH O—H
CH2 O—H
Glycerol
O
+ 3 RC—O- Na+
Sodium stearate, a soap
Acids + Amines --> AMIDES
N-methylacetamide
Acids + Amines --> AMIDES
Acetoaminophen
Tylenol, Datril, Momentum, ...