Biochemistry What does Organic Mean? Biochemistry: Packet #3 - Organic Chem.
Organic and Biochemistry
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Transcript of Organic and Biochemistry
Organic and Biochemistryorganic chemistry:
-- molecular shape is crucial
3-D structure ofsalicylic acid
3-D structure ofacetylsalicylic acid
(asp
irin)
the study of carbon-containing compounds
biochemistry: the chemistry of living things
Carbon is unique amongthe elements because:
it can have up to four bonds per C atom --
single, double, or triple bonds
--
--
it can form REALLY long chains of C atoms
its bonds are strong
–C–C– C=C –C=C–
Basic Definitions
hydrocarbons: compounds containing only __ and __
alkanes: hydrocarbons having only ______ bonds single
-- ALKANES = FUEL
–C–C–C–
–C–
H H
HHH
H
HHHH
–C–C–C–C–
H H HH
H HH H HH
H C
-- very stable; no rxn w/acids, bases, strong oxidizers
-- –anes are saturated
structural isomers: same molecular formula, different…bonding arrangements
alkenes: hydrocarbons having at least one ____ bond C=C
alkynes: hydrocarbons having at least one ____ bond C=C
C=CH
C
H
HH H
H
H–C–C=C–C–C–C–H
H
H
H H H
H H H
CH2CHCH3
CH3CC(CH2)2CH3
The simplest alkyne,ethyne (i.e., acetylene)– C2H2 – is the fuel in oxyacetylene torches.
aromatic hydrocarbons: benzene and compounds w/a benzene-related structure
-- –enes, –ynes,and aromaticsare __________ unsaturated
6 C atoms in a planar ringw/“tweener” bonds (C6H6)
August Kekule(1829–1896), whoclaimed that a dreamgave him insight into the structure of benzene.
“Finer-Point” Definitions
Straight-chain compounds have…
a single carbon backbone.
Branched-chain compounds have…
a main carbon backboneAND one or more branches
Substituted compounds have…
one or more H atomsremoved, with otheratoms in their place(s)(often halogens) Br
CH3(CH2)3CH3
C8H18
C5H11Br
C5H12
CH3CH2CH2CH2CH3
Branches and H-replacing atoms/groupsare collectively called… substituents.
–C–C–C–C–C–C–
HCl
HH
HCl
HH
HCl
HHPolyvinylchloride (PVC) is a material
made of long-chain carbons that havemany chloride substituents.
Functional group: a characteristic pattern that makes up a portion of a larger m’cule
-- specific atoms, specific bonding arrangements
-- importance: fgs largely determine the behaviorof their m’cules
–OH
alcohols ketones carboxylic acids
–C–
=
O
–C–
=
O
OH
-- several examples of fgs:
O O
OH
–COOH
Many organic compoundsare combinations ofseveral categories.
Cl
OH
Cl
O
OH
O Br
C6H11Br
Brsub.
br. + sub.
C10H21Cl
fg + sub.
C6H13OCl
fg
C6H12O2
fg + sub. + br.
C9H17OBr
Organic Nomenclature
Memorize the prefixes that tellthe # of C atoms in a chain.
1 =2 =3 =4 =5 =6 =7 =8 =9 =
10 =
meth–eth–prop–but–pent–hex–hept–oct–non–dec–
pent–
non–
dec–
hept–
Naming Straight-Chain Alkanes
1. Find the longest continuous chain of C atoms. Choose the appropriate prefix.
2. The name ends with –ane.
Provide the counterpart to the given.
propane
heptane
(C3H8)
(C7H16)
Alkanes: modification for substituent hydrocarbon (HC) groups
1. Number the “longest chain” carbons. Start with the end nearest a branch.
2. Name and give the #ed location of each substituent.
-- HC substituent groups use the prefixes, but end in –yl.
3. List substituents in alphabetical order.
(i.e., branches)
Provide each counterpart.
4-ethyl-2-methylhexane
octane
1
2
3
4
5
6
7
8
5-ethyl-3-methyl
(C11H24)
(C9H20)
Alkanes: modification for non-HC substituents
1. The “longest chain” MUST contain the substituent.
-- example substituents:
–NO2 –NH2 –F –Br –I nitro amino fluoro bromo iodo
2. Number the chain carbons, starting with the end nearest a substituent.
-- A non-HC substituent takes precedence over an HC branch.
3. Name and give the #ed location of each substituent.
-- If necessary, choose #s so that their sum is as low as possible.
Provide each counterpart.
3-bromo-2-chlorohexane
heptane
2-methyl-1-nitrobutane
heptane2-amino-6-nitro-3-propyl
2-ethyl-1,1-diiodo I
I
Cl
Br
NO2
NH2 NO2
Alkanes: modification for cycloalkanes
-- Use the cyclo- prefix before the word “alkane.”
Provide each counterpart.
1-bromo-1-chloro-2-methylcyclopentane
ethyl
Br
Cl
(C6H10BrCl)
(C8H16)
cyclohexane