Download A Crash Course In Organic Chemistry

A Crash Course
In Organic
Chemistry
Organic Chem
Study of organic chemistry and life
 Study of organic compounds in life
 Study of hydrocarbon compounds in
and their uses in life

Alkanes (CnH2n+2)
Number of
Carbons
Prefix
Structure
1
Methane
CH4
2
Ethane
CH3CH3
3
Propane
CH3CH2CH3
4
Butane
CH3(CH2)2CH3
5
Pentane
CH3(CH2)3CH3
6
Hexane
CH3(CH2)4CH3
7
Heptane
CH3(CH2)5CH3
8
Octane
CH3(CH2)6CH3
9
Nonane
CH3(CH2)7CH3
10
Decane
CH3(CH2)8CH3
11
Undecane
CH3(CH2)9CH3
12
Dodecane
CH3(CH2)10CH3
Naming Branched Alkanes






Find the longest carbon chain and name alkane
Number the carbon from the end with nearest
substituent (side group)
Determine the name of substituent and add –yl;
halogens are chloro, fluoro, iodo
Put the names in alphabetical order
Identify the positions of all substituents in the
name by placing the carbon number where the
substituent attaches to the parent chain in front
of it.
Arrange in alphabetical order and list each one
Naming
2,2,4-trimethyl-3-propylhexane
3-ethyl-3-methyl-4,5-dipropyloctane
6-ethyl-4,5-dipropylnonane
Naming
http://www.sciencegeek.net/APchemistry/APtaters/alkanes.htm
4-ethyl-3-methyl-4-propyloctane
2,2,3-trimethylpentane
4,4-diethyl-2,3-dimethylheptane
Reactions of Alkanes
1.Combustion: reaction with O2 in the
presence of sparks
Natural gas
CH4(g) + 2 O2(g)
disposable cigarette lighters
2 C4H10(g) + 13 O2(g)
charcoal lighter fluid
C5H12(g) + 8 O2(g)
hydrocarbons in gasoline
2 C8H18(l) + 25 O2(g)
CO2(g) + 2 H2O(g)
8 CO2(g) + 10 H2O(g)
5 CO2(g) + 6 H2O(g)
16 CO2(g) + 18 H2O(g)
2. Halogenation: reaction with halogens
(I, Br, F, Cl) to form alkyl halides
In the presence of light, or at high temperatures, alkanes
react with halogens to form alkyl halides:
light
CH4(g) + Cl2(g)
CH3Cl(g) + HCl(g)
light
CH4(g) + Br2(l)
CH3Br(g) + HBr(g)
Halogenation



A substitution reaction where H is
substituted by a halogen
The reactivity of the halogens is
F2>Cl2>Br2>I2
The reaction of halogen with methane or
ethane will form on product since the
reactivity of all of the hydrogens is exactly
the same
C2H6
C2H5-Cl + HCl
Halogenation
Halogenation of propane up to decane
generate more than one alkyl halides since
the Hs in the alkanes exhibit different
reactivities to halogen
 The reactivity of the Hs:
3o >2o >1o
1o- a C bound to one C
2o- a C bound to two C
H
o- a C bound to three C
3
CH3-C-CH -CH3

CH3
2
Halogenation


Halogenation of an alkane with more than
one type of H will generate more than one
alkyl halide called isomers
Same chemical formula but different
structures
CH3-CH2-CH3 + Cl2 ——> 45% CH3-CH2-CH2Cl + 55% CH3-CHCl-CH3
CH3-CH2-CH3 + Br2 ——> 3% CH3-CH2-CH2Br + 97% CH3-CHBr-CH3
(CH3)3CH + Cl2 ——> 65% (CH3)3CCl + 35% (CH3)2CHCH2Cl
Alkenes (CnH2n)
Number of Carbons
Prefix
Structure
2
Ethene
CH2=CH2
3
Propene
CH2=CHCH3
4
Butene
CH2=CHCH2CH3
5
Pentene
CH2=CH(CH2)2CH3
6
Hexene
CH2=CH(CH2)3CH3
7
Heptene
CH2=CH(CH2)4CH3
8
Octene
CH2=CH(CH2)5CH3
9
Nonene
CH2=CH(CH2)6CH3
10
Decene
CH2=CH(CH2)7CH3
11
Undecene
CH2=CH(CH2)8CH3
12
Dodecene
CH2=CH(CH2)9CH3
Naming Alkenes
1. Name the longest carbon chain that contains the
double bond
2. The name for the alkenes ends in ene instead of
–ane
3. Number the main chain from the end nearest the
double bond.
4. Indicate the position of the double bond with the
number of the first unsaturated carbon.
5. Place the number and names of substituents in
front of the alkene name.
6. Cyclic alkenes are named as cycloalkenes.
Naming Alkenes
2-methyl-2-pentene
CH3
CH3
CH2
CH
CH
CH2
3-methyl-1-pentene
Reactions of Alkenes
REACTANT REACTION
H2
Hydrogenation
(catalyzed by
metals)
H2O
Hydration
(catalyzed by
acid)
X2
Halogenation
HX
Hydrohalogenation
KmnO4,
Oxidation
H2O, and
OH-
EXAMPLE
CH2=CH2 → H-CH2-CH2-H
CH2=CH2 → H-CH2-CH2-OH
CH2=CH2 → Cl-CH2-CH2-Cl
CH2=CH2 → Cl-CH2-CH2-H
CH2=CH2 → OH-CH2-CH2-OH
Alkynes (CnH2n-2)
Number of Carbons
Prefix
Structure
2
Ethyne
CHΞCH
3
Propyne
CHΞCCH3
4
Butyne
CHΞCCH2CH3
5
Pentyne
CH ΞC(CH2)2CH3
6
Hexyne
CH ΞC(CH2)3CH3
7
Heptyne
CH ΞC(CH2)4CH3
8
Octyne
CH ΞC(CH2)5CH3
9
Nonyne
CH ΞC(CH2)6CH3
10
Decyne
CH ΞC(CH2)7CH3
11
Undecyne
CH ΞC(CH2)8CH3
12
Dodecyne
CH ΞC(CH2)9CH3
Naming Alkynes
1. Name the longest carbon chain that contains the
triple bond
2. The name for the alkenes ends in yne instead of
–ane
3. Number the main chain from the end nearest the
triple bond.
4. Indicate the position of the triple bond with the
number of the first unsaturated carbon.
5. Place the number and names of substituents in
front of the alkyne name.
Reactions of Alkynes
REACTANT REACTION
H2
Hydrogenation
(catalyzed by
metals)
H2O
Hydration
(catalyzed by
acid)
X2
Halogenation
HX
Hydrohalogenation
KmnO4,
Oxidation
H2O, and
OH-
EXAMPLE
CHΞCH → CH2=CH2
CHΞCH → CH2=CH-OH
CHΞCH → Cl-CH=CH-Cl
CHΞCH → Cl-CH=CH2
CHΞCH → OH-CH=CH-OH
Derivatives of
Hydrocarbons
A functional group is a reactive
portion of a molecule that undergoes
predictable reactions.
 All other organic compounds can be
considered to be derivatives of
hydrocarbons

Organic Functional Gps
Organic Compounds
Containing Oxygen

Many of the important functional groups
in organic compounds contain oxygen

Examples are
 alcohols
 ethers
 aldehydes
 ketones
 carboxylic acids
 esters
Alcohols

An alcohol is a compound obtained by
substituting a hydroxyl group (-OH) for
a –H atom on a carbon atom of a
hydrocarbon group.
• Some examples are
CH3 OH
methanol
CH3 CH2 OH
ethanol
OH
CH3
CH
CH3
2-propanol
Alcohols

An ether is a compound with an
oxygen “bridge” between two alkyl
groups.
• An example is
CH3 CH2 O CH2 CH3
diethyl ether

An aldehyde is a compound containing
a carbonyl group with at least one H
atom attached to it.
• An example is
O
CH3 CH
ethanal

A ketone is a compound containing a
carbonyl group with two hydrocarbon
groups attached to it.
• An example is
O
CH3 CH2 C CH3
2-butanone

A carboxylic acid is a compound
containing the carboxyl group, -COOH.
• An example is
O
CH3
C
OH
ethanoic acid

An ester is a compound formed from a
carboxylic acid, RCOOH, and an alcohol,
R’OH.
• The general structure is
O
R
C
O
R'

Most organic bases are amines, which
are compounds that are structurally
derived by replacing one or more
hydrogen atoms of ammonia with
hydrocarbon groups.
H
H
N
R'
R'
R
primary amine
H
N
R
secondary amine
R"
N
R
tertiary amine

Amides are compounds derived from
the reaction of ammonia, or of a
primary or secondary amine, with a
carboxylic acid.
• The general formula for a common
amide is
R
O
H
C
N
H
Groupings of Organic Compounds
Organic Comounds
Aliphatic compounds
contain straight or branched chains or
rings containing single carbon bonds
Aromatic compounds
carbon-based rings or multi-rings with
alternating single & double carbon bonds
Aromatic Compounds





ring compounds: bonds alternate between
single & double ones (bonds actually
resonate)
most common is benzene
when one hydrogen is replaced: name by
placing the name of the substituent first,
followed by -benzene
when two hydrogens replaced: ortho (o-),
meta (m-) or para (p-) used
when more hydrogens replaced: use
numbering system for positions on the
Benzene
benzene
naphthalene
Polycyclic Aromatic
Hydrocarbons (PAHs)





two or more benzene rings fused
together, sharing pairs of carbon atoms
PNAs: polynuclear aromatic compounds
PCBs: Polychlorinated biphenyls
PCDDs: Polychlorinated dibenzodioxins
PCDFs: Polychlorinated dibenzofurans
anthracene
General
Anesthetics
Ether and Chloroform

These agents are the anesthetics
from hell
Have negative side effects
 Flammable and very toxic

CH3-CH2-O-CH2-CH3
Non Halogenated
Hydrocarbons



all of these will work, and the longer the
chain, the higher the potency.
However, they have a tendency to produce
cardiovascular toxicity.
Cyclopropane (U.S.P.) is the only one still
in use, and it is explosive.
Ethers



Like hydrocarbons, the longer the
chain, the more potent the
anesthetic.
However, increasing chain length also
increases toxicity and reduces induction
time.
Ethyl ether is seldom used, and divinyl
ether is explosive and produces deep
anesthesia too quickly.
CH3-CH2-O-CH2-CH3
Halogenated Hydrocarbons-Cl




Addition of a halogen can reduce or eliminate
flammability, and can also increase potency.
Depending on the halogen, some of these
compounds can cause arrhythmias and/or
renal or hepatic toxicity.
Compounds containing only bromine are
generally not useful. Compounds containing
only chlorine are subject to limited use, are
toxic, and can cause arrhythmias.
The best of the chlorinated agents are ethyl
chloride and trichloroethylene
Chlorinated
ethylchloride
trichloroethylene
Halogenated-F




Fluorinated hydrocarbons are the most useful
of the general anesthetics
Were first discovered as offshoots of the
nuclear weapons program
Addition of a fluorine decreases flammability,
boiling point and the incidence of catecholinduced arrhythmias (these increase as the
size of the halogen increases, and F is the
smallest halogen).
The structures of a few representative
fluorinated hydrocarbon general anesthetics
are shown
Halogenated
Chlorinated and Fluorinated
(these are inhaled)
halothane
isoflurane
sevoflurane
enflurane
desflurane
Fluorinated




Halothane, USP (Fluothane) - the first fluorinated
hydrocarbon to be introduced, is a poor muscle
relaxant, and has some toxicity and propensity to
cause catechol-induced arrhythmias.
Methoxyflurane (Penthrane) - this analog is
somewhat better, but still causes some arrhythmias
and other toxicity. It also causes a slow induction
period.
Enflurane, U.S.P. (Enthrane) - good anesthetic, but
has unsatisfactory analgesia in Stage I.
Isoflurane (Forane) - the best general anesthetic so
far, it has no commonly observed ill effects.
Nitrous Oxide




This is the least toxic anesthetic
It is the least potent anesthetic
It causes good analgesia, but is a poor
muscle relaxant.
It is an NMDA receptor antagonist so
prevent transmission of signals between
neurons in the brain
N2O
Barbiturates (IV)



Derivatives of barbit acid
act as central nervous
system depressants,
produce a wide spectrum
of effects, from mild
Barbituric acid
sedation to anesthesia
Activate the GABA
receptor. GABA is the
M
principal inhibitory
neurotransmitter in the et
h Na thiopental
mammalian Central
Nervous System (CNS).oh
e
Methohexital
Benzodiazepines (IV)



Psychoactive drugs
Used before certain
medical procedures such
as endoscopies or dental
work and prior to some
unpleasant medical
procedures in order to
induce sedation and
amnesia for the procedure
Activates the GABA
receptor
diazepam
midazolam
lorazepam
Propofol
a short-acting
intravenous anesthetic
agent
used for the induction
of general anesthesia
in adult patients and
pediatric patients older
than 3 years of age
Activates the GABA
receptor-inhibits signal
transmission in the
brain
Etomidate
short acting
intravenous anesthetic
agent
used for the induction
of general anaesthesia
and for sedation for
short procedures
Ketamine HCl (IV)





deriv of phencyclidine
acts like a volatile
anesthetic agent
It is potent, rapid acting
and has a short duration
Patients older than 16 will
often (27%) have wild
dreams and hallucinations
during emergence, and so
only indicated for children
less than 16 years old.
NMDA receptor antagonist
Local
Anesthetics
Local Anesthetics



Local anesthetics are agents which
prevent transmission of nerve impulses
without causing unconsciousness.
They act by binding to fast sodium
channels from within (in an open state).
Local anesthetics can be either ester or
amide based.
Local Anesthetics

Have the following general structure:
 Aromatic-benzene ring-hydrophobic
 Intermediate-amide or ester portion
 Amino portion-hydrophyllic
Amino Esters
procaine
tetracaine
chloroprocaine
cocaine
Amino Amides
bupivicaine
cinchocaine
prilocaine
levobupivicaine
lidocaine
ropivacaine
Common Local Anesthetics
Duration w/o
Epi,
min
Duration W/
Epi,
min
Maximum
Dose w/o Epi,
mg/kg
Maximum
Dose W/ Epi,
mg/kg
Cocaine
45
-
2.8
-
Procaine
15-30
30-90
7.1
8.5
Chloroprocaine
30-60
-
11.4
14.2
120-240
240-480
1.4
-
Lidocaine
30-120
60-400
4.5
7
Mepivacaine
30-120
30-120
4.5
7
Bupivacaine
120-240
240-480
2.5
3.2
Etidocaine
200
240-360
4.2
5.7
Prilocaine
30-120
60-400
5.7
8.5
Anesthetic
Esters
Tetracaine
Amides