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Principles of Chemistry II © Vanden Bout
Today
Organic
Carbon Chemistry
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Principles of Chemistry II © Vanden Bout
Organic
You know more than you think already
What you will needLewis dot, VSEPR
VB, hybrid orbitals, MOelectronegativity
intermolecular forces
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Two hurdles we will deal with
Understanding structuresNomenclature
IbuprofenRS)-2-(4-(2-methylpropyl)phenyl)propanoic acid
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R)-3,4-dihydroxy-5-((S)- 1,2-dihydroxyethyl)furan-2(5H)-oneL-ascorbic acid
vitamin C
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First Structures
Let’s look at a simple moleculebutane C4H10
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A. 0
B. 4
C. 5
D. 6
E. 7
How many carbon atoms does this molecule have?
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A. 6
B. 10
C. 12
D. 14
E. 16
How many hyrdogen atoms does this molecule have?
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How many carbons and hydrogens in the following?
A. 6 C, 14 H
B. 6 C, 15 H
C. 6 C, 16 H
D. 7 C, 15 H
E. 7 C, 14 H
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How many carbons and hydrogens in the following?
A. 6 C, 14 H
B. 6 C, 15 H
C. 6 C, 16 H
D. 7 C, 15 H
E. 7 C, 14 H
3H
3H
3H
2H
1H
1H
1H
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Principles of Chemistry II © Vanden Bout
this is the structure for caffeine
how many hydrogens are not shown?
A. 0
B. 1
C. 2
D. 3
E. 4
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Step 1
Nomenclature
prefix parent suffix
parent is the name of the longest carbon chain. Each length has a given name
1 carbon methane2 carbons ethane5 carbons pentane
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Step 1
Nomenclature
prefix parent suffix
suffix is the name of the "functional group"
-ol alcohol-one ketone-ane alkane
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Principles of Chemistry II © Vanden Bout
Step 1
Nomenclature
prefix parent suffix
prefix is the name of any substituent groups typically a carbon chain(sidechains)
1 carbon methyl2 carbons ethyl5 carbons pentyl
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Names for parent groups
First lets look at alkanes(essentially no functional group)
All single bonds
suffix is ane
methane butane 5-methyloctane
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Principles of Chemistry II © Vanden Bout
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The following compound is
A. butane
B. isobutane
C. pentane
D. hexane
E. heptane
CH3CH2CH2CH2CH2CH3
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What about sidechains?
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The following compound is
A. 3-ethylhexane
B. 3-ethylpropane
C. 4-propylhexane
D. 4-ethylheptane
E. 3-ethylocatne
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Which numbers do I use?
longest main chainlowest possible numbers
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The next simplestadd a functional group
C=C Double bond
suffix -ene
C=C Triple bond
suffix -yne
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Principles of Chemistry II © Vanden Bout
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The following compound is
A. 2-hexene
B. 3-hexene
C. 4-heptene
D. 4-hexene
E. 2 methyl, butene
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The following compound is
A. 5-methyl 2-hexene
B. 2-methyl 5-hexene
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Nomenclature with functional group
Put the number by before the functional group suffix
old system(everyone uses)
1 butene
official IUPACname
but-1-ene
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Name this compound
A. 2-methyl 5-pentene
B. 2-methyl 3-hexene
C. 1,1-dimethyl 2-pentene
D. 5-methyl 3-hexene
E. 5-methyl 4-hexene
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Other side-chains
HalogensF FluoroCl ChloroBr BromoI Iodo
OH grouphydroxy
NH2 groupamino
Benzene Ringphenyl
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Cyclic Hydrocarbonsthe carbon chain connects back to itself
cyclobutane
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Structural Isomers
hexane (C6H14)
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Are these the same molecule?
A. YesB. No
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Structural Isomer(constitutional isomers)
Stereo Isomer(spatial isomers)
Same atoms and bonds, different bonding pattern
Same bonding pattern, different orientations in space
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Structural isomers
n-hexane 2 methyl pentane
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StereoisomersDiastereomer(can interconvert)
cis dichloro ethene trans dichloroethene
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Stereoisomers Enantiomers(chiral molecules)
Molecules cannot be superimposed(left and right hand versions)
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Chiral Center(place where the chirality arises)
Carbon (or other atom)with 4 different substituents
R)-3,4-dihydroxy-5-((S)- 1,2-dihydroxyethyl)furan-2(5H)-oneL-ascorbic acidvitamin C
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IbuprofenRS)-2-(4-(2-methylpropyl)phenyl)propanoic acid
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Dienes
Two double bonds
5 carbon chain, parent penta
no side chains
two double bonds dieneposition 1 and 3
penta-1,3-diene
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Alkyne
Carbon Carbon Triple Bond
Suffix -yne
2 methyl hex-3-yne
1
2345
6
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Other functional groups
RR = Generic representation of the rest of the molecule
OHfunctional group
-OH group is an alcoholsuffix is -ol
CommonEthanol
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Name this compound
A. heptan-2-ol
B. hexan-4-ol
C. 2-ethylbutan-1-ol
D. 2-ethylpentan-1-ol
E. hexan-3-ol
OH
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Ketone
Rcarbon double bonded to an oxygen
bonded to carbons on either sidesuffix is -one
CO
R
CommonAcetone
(nail polish remover)
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Principles of Chemistry II © Vanden Bout
Which of the following is a ketone?
A. A
B. B
C. C
D. A & B
E. all three
O O O
O
A B C
butan-3-one
H
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Aldehyde
Rcarbon double bonded to an oxygen
bonded to carbon on one side (like a ketone at the end of a chain)
suffix is -al
CO
H
CommonFormaldehyde
(Fetal Pig Storage)
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Name this compound
A. hex-3-enal
B. hex-3-en-1-al
C. hex-3-en-6-al
D. hex-6-al-3-ene
E. hexene6-3-al
O
No need to number aldehydeits always at the end
H shown to emphasize thefunctional group
H
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Carboxylic Acid
Rcarbon double bonded to an oxygen
bonded to carbon on one side OH on the other side
suffix is -oic acid
CO
OH
CommonAcetic Acid(vinegar)
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Name this compound
A. methanoic acid
B. ethanoic acid
C. propanoic acid
D. 3 hydroxy propan-2-one
E. propanol
OH
No need to number carboxylic acidits always at the end
this compound is alsocommonly known as acetic acid
O
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Ester
Rcarbon double bonded to an oxygen
bonded to carbon on one side OR on the other side
suffix is -oic acid
CO
O
Commonlots of flavorings
R'
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Name this compound
A. ethyl butanoate
B. butyl methanoate
C. methyl heptanoate
D. butyl ethanoate
E. pentyl ethanoate
O
No need to number estername the two sides
part with the carboxyl (C=O)is the parent
other part is like the side chain
O
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Ether
R
carbon oxygen in the middle of the chainsuffix is -ether
ODiethyl Ether
(knocks you out)
R'
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O
Treat as two "side chains"
methyl ethyl ether
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Primary Amine
R NH2
-NH2 group is an aminesuffix is -amine
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Amide
Rcarbon double bonded to an oxygen
bonded to carbon on one side N on the other side
suffix is -amide
CO
N R'R"
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Naming amide Treat part with C=O as parentparts on the N as sidechains
O
NH2
pentanamide
O
N
N-ethyl-N-methylpentanamide
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NH2
O
O
O
N
Amine
Ether
Ketone
Amide
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OH
O
O
O
Alcohol
Carboxylic Acid
Ester
Alkene
OH
OH
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Important Reaction for Biochemistry
Formation of an Amide
The don't call them functional groups for nothing
Carboxylic Acid
RC
O
OH
Primary Amine
NH
R'H
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Carboxylic Acid
RC
O
OH
Primary Amine
NH
R'H
Amide + Water
RC
O
N R'H
+ H2O
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Amino Acid
CC
O
OH
R
H2N
Carboxylic End and Amine EndCan react with itself
(or similar molecules) in a chain
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Polypeptide
Two distinct endsN-terminus is an amine
C-terminus is a carboxylic acid
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Carboxylic Acid
RC
O
OH
Alcohol
OH
R'
Ester + Water
RC
O
O R' + H2O
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Triglycerides
Gylcerol
OHOH
HO
Fatty Acid(carboxylic acid with long chain)
C12H25COOH
Makes Trigylceride
OCC12H25
OCC12H25
C12H25COO
OO
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The three fatty acids canall be the same or different
High levels of triglycerides is linked tobuild up of plaque in the arteries
= heart disease
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Alcohol
ROH
Alcohol
HOR'
Ether + Water
RO
R' + H2O
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Sugars
Glucose(key factor for sugars lots of hydroxyls)
They can react to form chains of sugarspolysaccharide
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Celluose
Very long ether chain(pretty much all plant material)
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Polysaccharide (Starch)
Sugars, Carbohydratesmonosaccharides (one)
disaccharides (two)polysaccharides (many)
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Condensation Reactions(two molecules make one + water)
Carboxylic Acid + Amine = Amide + water
Carboxylic Acid + Alcohol = Ester + water
Alcohol + Alcohol = Ether + water