chapter 4: carbon. carbon overview: carbon—the backbone of biological molecules all living...
TRANSCRIPT
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Chapter 4: CarbonChapter 4: Carbon
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CarbonCarbon
• Overview: Carbon—The Backbone of Biological Molecules
• All living organisms are made up of chemicals based mostly on the element carbon
• Organic chemistry is the study of carbon compounds
• Overview: Carbon—The Backbone of Biological Molecules
• All living organisms are made up of chemicals based mostly on the element carbon
• Organic chemistry is the study of carbon compounds
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The Formation of Bonds with CarbonThe Formation of Bonds with Carbon
Carbon has FOUR unpaired valence electrons
This allows it to form FOUR covalent bonds with a variety of atoms
Carbon has FOUR unpaired valence electrons
This allows it to form FOUR covalent bonds with a variety of atoms
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Versatility of CarbonVersatility of Carbon
• The bonding versatility of carbon
• Allows it to form many diverse molecules, including carbon skeletons
• The bonding versatility of carbon
• Allows it to form many diverse molecules, including carbon skeletons
(a) Methane(a) Methane
(b) Ethane(b) Ethane
((c) Ethene c) Ethene (ethylene)(ethylene)
Molecular Molecular FormulaFormula
Structural Structural FormulaFormula
Ball-and-Ball-and-Stick ModelStick Model
Space-Filling Space-Filling ModelModel
HH
HH
HH
HH
HH
HH
HH
HH
HH
HH
HH HH
HHHH
CC
CC CC
CC CC
CHCH44
CC22HH
66
CC22HH44
Name andName and Comments Comments
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Common Bonding Partners of Carbon
Common Bonding Partners of Carbon
• The electron configuration of carbon
• Gives it covalent compatibility with many different elements
• The electron configuration of carbon
• Gives it covalent compatibility with many different elements
HH OO NN CC
HydrogenHydrogen
(valence = 1)(valence = 1)
OxygenOxygen
(valence = 2(valence = 2))
NitrogenNitrogen
(valence = 3)(valence = 3)
CarbonCarbon
(valence = 4)(valence = 4)
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HH
HHHH
HH
HH
HH HH HH
HH
HH
HH
HH HH HH
HH HH HH
HH HH
HH
HH
HH
HH
HH
HH
HH
HH
HH
HH HH HH HH
HH HH
HH HH
HH HH HH HH
HH HH
HH HH
HHHH
HHHH
HH
HH
HH
CC CC CC CC CC
CC CC CC CC CC CC CC
CCCCCCCCCCCCCCCC
CC
CC
CC
CC
CC
CC
CC
CCCC
CC
CC
CC
HH
HH
HH
HHHH
HH
HH
Length
Branching
Double bonds
Rings
Ethane Propane
Butane2-methylpropane
(commonly called isobutane)
1-Butene 2-Butene
Cyclohexane Benzene
HH HH HH HHHH
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HydrocarbonsHydrocarbons
Hydrocarbons
Are molecules consisting of only carbon (C) and hydrogen (H)
The bonds between the C and H atoms are non-polar covalent
This makes hydrocarbons hydrophobic
Hydrocarbons
Are molecules consisting of only carbon (C) and hydrogen (H)
The bonds between the C and H atoms are non-polar covalent
This makes hydrocarbons hydrophobic
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IsomersIsomers
Isomers
Are molecules with the same molecular formula but different structures and properties
• Three types of isomers are:
• Structural
• Geometric
• Enantiomers
Isomers
Are molecules with the same molecular formula but different structures and properties
• Three types of isomers are:
• Structural
• Geometric
• Enantiomers
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Structural isomers: Structural isomers: BranchingBranching
2-methyl butane2-methyl butanePentanePentane
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Geometric isomers: Geometric isomers: Double Double BondsBonds
ciscis isomer: The two Xs are isomer: The two Xs areon the same side.on the same side.
transtrans isomer: The two Xs areisomer: The two Xs areon opposite sides.on opposite sides.
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Enantiomers: Enantiomers: MirroredMirrored ImagesImages
AsymmetricAsymmetric Carbon Carbon
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The Functional GroupsThe Functional Groups
Functional groups
Are the chemically reactive groups of atoms within an organic molecule
They behave consistently and characteristically, giving unique properties to the molecules possessing them.
Functional groups
Are the chemically reactive groups of atoms within an organic molecule
They behave consistently and characteristically, giving unique properties to the molecules possessing them.
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STRUCTURE
EXAMPLE
NAME OFCOMPOUND
FUNCTIONALPROPERTIES
Methyl
5-Methyl cytidine is a component of DNA that has been modified by addition of the methyl group.
5-Methyl cytidine
Methylated compounds
Addition of a methyl group to DNA, or to molecules bound to DNA, affects expression of genes.
Arrangement of methyl groups in male and female sex hormones affectstheir shape and function.
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HydroxylHydroxyl
Composition: Oxygen bonded to a Hydrogen atom as well as a Carbon
Structure: -C-OH
Methanol:
Can also be seen as HO-C-
Not to be confused with hydroxide ion (OH-)
Compounds containing hydroxyl groups are called alcohols
Makes molecules polar (hydrophilic)
Composition: Oxygen bonded to a Hydrogen atom as well as a Carbon
Structure: -C-OH
Methanol:
Can also be seen as HO-C-
Not to be confused with hydroxide ion (OH-)
Compounds containing hydroxyl groups are called alcohols
Makes molecules polar (hydrophilic)
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CarbonylCarbonyl
Composition: Oxygen double bonded to a Carbon
Structure: -C=O
Aldehyde: If at end of carbon skeleton
Ketone: If in middle of carbon skeleton
Composition: Oxygen double bonded to a Carbon
Structure: -C=O
Aldehyde: If at end of carbon skeleton
Ketone: If in middle of carbon skeleton
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STRUCTURE
EXAMPLE
NAME OFCOMPOUND
FUNCTIONALPROPERTIES
Carboxyl
Acetic acid, which gives vinegar its sour taste
Carboxylic acids, or organic acids
Has acidic propertiesbecause the covalent bond between oxygen and hydrogen is so polar; for example,
Acetic acid Acetate ion
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STRUCTURE
EXAMPLE
NAME OFCOMPOUND
FUNCTIONALPROPERTIES
Amino
Because it also has a carboxyl group, glycine is both an amine anda carboxylic acid; compounds with both groups are called amino acids.
Amines
Acts as a base; can pick up an H+ from the surrounding solution (water, in living organisms).
Ionized, with a charge of 1+, under cellular conditions.
(ionized)(nonionized)
Glycine
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STRUCTURE
EXAMPLE
NAME OFCOMPOUND
FUNCTIONALPROPERTIES
Sulfhydryl
(may be written HS—)
Cysteine
Cysteine is an important sulfur-containing amino acid.
Thiols
Two sulfhydryl groups can react, forming a covalent bond. This “cross-linking” helps stabilize protein structure.
Cross-linking ofcysteines in hairproteins maintains the curliness or straightness of hair. Straight hair can be “permanently” curled by shaping it around curlers, then breakingand re-forming thecross-linking bonds.
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STRUCTURE
EXAMPLE
NAME OFCOMPOUND
FUNCTIONALPROPERTIES
Phosphate
In addition to taking part in many important chemical reactions in cells, glycerol phosphate provides the backbone for phospholipids, the most prevalent molecules in cell membranes.
Glycerol phosphate
Organic phosphates
Contributes negative charge to the molecule of which it is a part (2– when at the end of a molecule; 1– when located internally in a chain of phosphates).
Has the potential to react with water, releasing energy.