Organic Chemistry Chapter 03. Organic Chemistry 2Outline Organic vs Inorganic Functional Groups and...
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Transcript of Organic Chemistry Chapter 03. Organic Chemistry 2Outline Organic vs Inorganic Functional Groups and...
Organic Chemistry
Chapter 03
2Organic ChOrganic Chemistryemistry
OutlineOutline
Organic vs InorganicOrganic vs Inorganic
Functional Groups and IsomersFunctional Groups and Isomers
MacromoleculesMacromolecules
CarbohydratesCarbohydrates
LipidsLipids
ProteinsProteins
Nucleic AcidsNucleic Acids
3Organic ChOrganic Chemistryemistry
Organic MoleculesOrganic Molecules
Inorganic – Chemistry of elements other than carbonInorganic – Chemistry of elements other than carbonOrganic – Carbon-based chemistryOrganic – Carbon-based chemistry
Usually associatedUsually associatedliving systemsliving systems
Often associated with Often associated with nonliving matternonliving matter
Often quite large, withOften quite large, withmany atomsmany atoms
Always withAlways withfew atomsfew atoms
AlwaysAlwayscovalent bondingcovalent bonding
UsuallyUsuallyionic bondingionic bonding
Always containAlways containcarbon and hydrogencarbon and hydrogen
Usually withUsually with+ & - ions+ & - ions
OrganicOrganicInorganicInorganic
4Carbohydrates as structural materials
5Organic ChOrganic Chemistryemistry
Carbon AtomCarbon Atom
Carbon atoms:Carbon atoms:
Contain a total of 6 electronsContain a total of 6 electrons
Only four electrons in the outer shellOnly four electrons in the outer shell
Very diverse as one atom can bond with up to Very diverse as one atom can bond with up to four other atomsfour other atoms
Often bonds with other carbon atoms to make Often bonds with other carbon atoms to make hydrocarbonshydrocarbons
Can produce long carbon chains like octaneCan produce long carbon chains like octane
Can produce ring forms like cyclohexaneCan produce ring forms like cyclohexane
6Octane & Cyclohexane
7Organic ChOrganic Chemistryemistry
Functional Groups and IsomersFunctional Groups and Isomers
Functional groupsFunctional groups::
Specific combinations of bonded atomsSpecific combinations of bonded atoms
Attached as a group to other moleculesAttached as a group to other molecules
Always react in the same manner, regardless of Always react in the same manner, regardless of where attachedwhere attached
Determine activity and polarity of large organic Determine activity and polarity of large organic moleculesmolecules
Many functional groups, but only a few are of Many functional groups, but only a few are of major biological importancemajor biological importance
8Organic ChOrganic Chemistryemistry
Polar; some sugarsPolar; some sugarsExample: AcetoneExample: Acetone
Polar, forms H-bonds; some sugarsPolar, forms H-bonds; some sugarsand amino acids Example: Ethanoland amino acids Example: EthanolR OH
RHCO
R RCO
ROHCO
RHN H
R SH
Biologically ImportantBiologically ImportantFunctional GroupsFunctional Groups
ThiolsThiols
PhosphatePhosphate
AminesAminesAminoAmino
CarboxylicCarboxylicAcidsAcidsCarboxylCarboxyl
KetonesKetones
AldehydesAldehydesCarbonylCarbonyl
AlcoholsAlcoholsHydroxylHydroxylCompoundCompoundStructureStructureGroupGroup
SulfhydrylSulfhydryl
R RCO
OH
OrganicOrganicPhosphatesPhosphates
SignificanceSignificance
Polar; some sugarsPolar; some sugarsExample: FormaldehydeExample: Formaldehyde
Polar, acidic; fats and amino acidsPolar, acidic; fats and amino acidsExample: Acetic acidExample: Acetic acid
Polar, basic; amino acidsPolar, basic; amino acidsExample: TryptophanExample: Tryptophan
Disulfide Bonds; some amino acidsDisulfide Bonds; some amino acidsExample: EthanethiolExample: Ethanethiol
Polar, acidic; some amino acidsPolar, acidic; some amino acidsExample: Adenosine triphosphateExample: Adenosine triphosphate
Polar, forms H-bonds; some sugarsPolar, forms H-bonds; some sugarsand amino acids; Example: Ethanoland amino acids; Example: Ethanol
Polar; some sugarsPolar; some sugarsExample: FormaldehydeExample: Formaldehyde
Polar; some sugarsPolar; some sugarsExample: AcetoneExample: Acetone
Polar, acidic; fats and amino acidsPolar, acidic; fats and amino acidsExample: Acetic acidExample: Acetic acidPolar, acidic; some amino acidsPolar, acidic; some amino acidsExample: Adenosine triphosphateExample: Adenosine triphosphate
Disulfide Bonds; some amino acidsDisulfide Bonds; some amino acidsExample: EthanethiolExample: Ethanethiol
Polar, basic; amino acidsPolar, basic; amino acidsExample: TryptophanExample: Tryptophan
9Organic ChOrganic Chemistryemistry
IsomersIsomers
IsomersIsomers - organic molecules that have: - organic molecules that have: Identical molecular formulas, butIdentical molecular formulas, butDiffering internal arrangement of atomsDiffering internal arrangement of atoms
10Organic ChOrganic Chemistryemistry
MacromoleculesMacromolecules
Some molecules called macromolecules because of Some molecules called macromolecules because of their large sizetheir large size
Usually consist of many repeating unitsUsually consist of many repeating units Resulting molecule is a polymer (many parts)Resulting molecule is a polymer (many parts) Repeating units are called monomersRepeating units are called monomers
Some examples:Some examples:
NucleotideNucleotideDNA, RNADNA, RNANucleic AcidsNucleic Acids
Amino acidAmino acidPolypeptidePolypeptideProteinsProteins
MonosaccharideMonosaccharidePolysaccharidePolysaccharideCarbohydratesCarbohydrates
Glycerol & fatty acidsGlycerol & fatty acidsFatFatLipidsLipids
Subunit(s)Subunit(s)ExampleExampleCategoryCategory
11Common Foods
12Organic ChOrganic Chemistryemistry
Dehydration and HydrolysisDehydration and Hydrolysis
DehydrationDehydration - Removal of water molecule - Removal of water moleculeUsed to connect monomers together to make Used to connect monomers together to make polymerspolymers
Polymerization of glucose monomers to make Polymerization of glucose monomers to make starchstarch
HydrolysisHydrolysis - Addition of water molecule - Addition of water moleculeUsed to disassemble polymers into monomer Used to disassemble polymers into monomer partsparts
Digestion of starch into glucose monomersDigestion of starch into glucose monomers
Specific enzymes required for each reactionSpecific enzymes required for each reactionAccelerate reactionAccelerate reactionAre not used in the reactionAre not used in the reaction
13Synthesis and Degradationof Polymers
14Organic ChOrganic ChemistryemistryFour Classes of Organics:Four Classes of Organics:
1 - Carbohydrates1 - Carbohydrates
MonosaccharidesMonosaccharides::Single sugar moleculeSingle sugar moleculeGlucose, ribose, deoxyriboseGlucose, ribose, deoxyribose
DisaccharidesDisaccharides::Contain two monosaccharides joined during Contain two monosaccharides joined during dehydration reactiondehydration reaction
SucroseSucrose
PolysaccharidesPolysaccharides::
Polymers of monosaccharidesPolymers of monosaccharidesStarch, cellulose, chitinStarch, cellulose, chitin
15Popular Models for Representing
Glucose Molecules
16Synthesis and Degradation
of Maltose, a Disaccharide
17Organic ChOrganic ChemistryemistryCarbohydrates Examples:Carbohydrates Examples:
MonosaccharidesMonosaccharides
Single sugar moleculesSingle sugar molecules
Quite soluble and sweet to tasteQuite soluble and sweet to taste
ExamplesExamplesGlucoseGlucose (blood), fructose (fruit) and galactose (blood), fructose (fruit) and galactose HexosesHexoses - Six carbon atoms - Six carbon atoms
Isomers of CIsomers of C66HH1212OO66
RiboseRibose and and deoxyribosedeoxyribose (in nucleotides) (in nucleotides) PentosesPentoses – Five carbon atoms – Five carbon atoms
CC55HH1010OO5 & 5 & CC55HH1010OO44
18Organic ChOrganic ChemistryemistryCarbohydrates Examples:Carbohydrates Examples:
DisaccharidesDisaccharides
Contain two monosaccharides joined by Contain two monosaccharides joined by dehydration reactiondehydration reaction
Soluble and sweet to tasteSoluble and sweet to taste
ExamplesExamplesSucroseSucrose Table sugar, maple sugarTable sugar, maple sugar One glucose and one fructose joined by One glucose and one fructose joined by dehydrationdehydration
MaltoseMaltoseMalt sugarMalt sugar Two glucoses joined by dehydrationTwo glucoses joined by dehydration
19Organic ChOrganic ChemistryemistryCarbohydrates Examples:Carbohydrates Examples:
Polysaccharides (1)Polysaccharides (1)
Polymers of monosaccharidesPolymers of monosaccharidesLow solubility; not sweet to tasteLow solubility; not sweet to tasteExamplesExamples
StarchStarchPolymer of glucosePolymer of glucoseUsed for short-term energy storageUsed for short-term energy storage
Plant starchPlant starchOften branched chainOften branched chain
AmyloseAmylose, corn starch, corn starchAnimal starchAnimal starch
UnbranchedUnbranchedGlycogenGlycogen in liver and muscles in liver and muscles
20Organic ChOrganic ChemistryemistryCarbohydrates Examples:Carbohydrates Examples:
Polysaccharides (2)Polysaccharides (2)
More polysaccharide examplesMore polysaccharide examplesCelluloseCellulose Long, coiled polymer of glucoseLong, coiled polymer of glucose Glucoses connected differently than in starchGlucoses connected differently than in starch Structural element for plantsStructural element for plantsMain component of wood and many natural Main component of wood and many natural fibersfibers Indigestible by most animalsIndigestible by most animals
ChitinChitin Polymer of glucosePolymer of glucose Each glucose with an amino groupEach glucose with an amino group Very resistant to wear and digestionVery resistant to wear and digestion Arthropod exoskeletons, cell walls of fungiArthropod exoskeletons, cell walls of fungi
21StarchStructure and
Function
22GlycogenStructure and
Function
23CelluloseStructure and
Function
24Organic ChOrganic ChemistryemistryFour Classes of Organics:Four Classes of Organics:
2 - Lipids2 - Lipids
Insoluble in waterInsoluble in water Long chains of repeating CHLong chains of repeating CH22 units units Renders molecule nonpolarRenders molecule nonpolar
Types of LipidsTypes of Lipids
MedicinesMedicinesComponent of plasma Component of plasma membrane; hormonesmembrane; hormonesSteroidsSteroids
No-stick pan sprayNo-stick pan sprayComponent of plasma Component of plasma membranemembranePhospholipidsPhospholipids
Cooking oilsCooking oilsLong-term energy storage in Long-term energy storage in plants and their seedsplants and their seedsOilsOils
Butter, lardButter, lardLong-term energy storage & Long-term energy storage & thermal insulation in animalsthermal insulation in animalsFatsFats
Human UsesHuman UsesOrganismal UsesOrganismal UsesTypeType
Candles, polishesCandles, polishesWear resistance; retain waterWear resistance; retain waterWaxesWaxes
25Blubber
26Types of Lipids:Triglycerides
27Organic ChOrganic ChemistryemistryTypes of Lipids:Types of Lipids:
Triglycerides (1)Triglycerides (1)
TriglyceridesTriglycerides (Fats) (Fats)Long-term energy storageLong-term energy storageBackbone of one Backbone of one glycerolglycerol molecule molecule Three-carbon Three-carbon alcoholalcohol Each has an OHEach has an OH-- group group
Three fatty acids attached to each glycerol Three fatty acids attached to each glycerol moleculemolecule Long hydrocarbon chainLong hydrocarbon chain
SaturatedSaturated - no double bonds between carbons - no double bonds between carbons UnsaturatedUnsaturated - - 1 double bonds between carbons1 double bonds between carbons
Carboxylic acid at one endCarboxylic acid at one end Carboxylic acid connects to –OH on glycerol in Carboxylic acid connects to –OH on glycerol in dehydration reactiondehydration reaction
28Dehydration Synthesis of Triglyceridefrom Glycerol and Three Fatty Acids
29Organic ChOrganic ChemistryemistryTypes of Lipids:Types of Lipids:
Phospholipids (2)Phospholipids (2)
PhospholipidsPhospholipidsDerived from triglyceridesDerived from triglycerides
GlycerolGlycerol backbone backboneTwo fatty acids attached instead of threeTwo fatty acids attached instead of threeThird fatty acid replaced by Third fatty acid replaced by phosphate groupphosphate group The fatty acids are nonpolar and hydrophobicThe fatty acids are nonpolar and hydrophobic The phosphate group is polar and hydrophilicThe phosphate group is polar and hydrophilic
Molecules self arrange when placed in waterMolecules self arrange when placed in waterPolar Polar phosphate phosphate ““headsheads”” next to water next to waterNonpolar Nonpolar fatty acid fatty acid ““tailstails”” overlap and overlap and exclude waterexclude water
Spontaneously form double layer & a sphereSpontaneously form double layer & a sphere
30Phospholipids Form Membranes
31Organic ChOrganic ChemistryemistryTypes of Lipids:Types of Lipids:
Steroids & Waxes (3)Steroids & Waxes (3)
SteroidsSteroids
Cholesterol, testosterone, estrogenCholesterol, testosterone, estrogen
Skeletons of four fused carbon ringsSkeletons of four fused carbon rings
WaxesWaxes
Long-chain fatty acid bonded to a long-chain Long-chain fatty acid bonded to a long-chain alcoholalcohol
High melting pointHigh melting point
WaterproofWaterproof
Resistant to degradationResistant to degradation
32Steroid Diversity
33Waxes
34Organic ChOrganic ChemistryemistryFour Classes of Organics:Four Classes of Organics:
3 -Proteins3 -Proteins
FunctionsFunctions
Support – CollagenSupport – Collagen
Enzymes – Almost all enzymes are proteinsEnzymes – Almost all enzymes are proteins
Transport – Hemoglobin; membrane proteinsTransport – Hemoglobin; membrane proteins
Defense – AntibodiesDefense – Antibodies
Hormones – Many hormones; insulinHormones – Many hormones; insulin
Motion – Muscle proteins, microtubulesMotion – Muscle proteins, microtubules
35Organic ChOrganic ChemistryemistryProtein Subunits:Protein Subunits:
The Amino AcidsThe Amino Acids
Proteins are polymers of Proteins are polymers of amino acidsamino acidsEach amino acid has a central carbon atom Each amino acid has a central carbon atom
(the alpha carbon) to which are attached(the alpha carbon) to which are attached a hydrogen atom,a hydrogen atom, an an amino groupamino group –NH –NH22,, A carboxylic acid group –COOH,A carboxylic acid group –COOH, and one of 20 different types of –and one of 20 different types of –RR
(remainder) (remainder) groupsgroupsThere are 20 different amino acids that make There are 20 different amino acids that make
up proteinsup proteinsAll of them have basically the same structure All of them have basically the same structure
except for what occurs at the placeholder except for what occurs at the placeholder RR
36Structural Formulas for the
20 Amino Acids
37Organic ChOrganic ChemistryemistryProteins:Proteins:
The Polypeptide BackboneThe Polypeptide Backbone
Amino acids joined together end-to-endAmino acids joined together end-to-end
COOH of one AA covalently bonds to the NHCOOH of one AA covalently bonds to the NH22 of the next AAof the next AA
Special name for this bond - Special name for this bond - Peptide BondPeptide Bond
Two AAs bonded together – Two AAs bonded together – DipeptideDipeptide
Three AAs bonded together – Three AAs bonded together – TripeptideTripeptide
Many AAs bonded together – Many AAs bonded together – PolypeptidePolypeptide
Characteristics of a protein determined by Characteristics of a protein determined by composition and sequence of AA’scomposition and sequence of AA’s
Virtually unlimited number of proteinsVirtually unlimited number of proteins
38Synthesis and Degradation of a Peptide
39Organic ChOrganic ChemistryemistryProtein Molecules:Protein Molecules:
Levels of StructureLevels of Structure
PrimaryPrimary:: Literally, the sequence of amino acidsLiterally, the sequence of amino acids A string of beads (up to 20 different colors)A string of beads (up to 20 different colors)
SecondarySecondary:: The way the amino acid chain coils or foldsThe way the amino acid chain coils or folds Describing the way a knot is tiedDescribing the way a knot is tied
TertiaryTertiary:: Overall three-dimensional shape of a polypeptideOverall three-dimensional shape of a polypeptide Describing what a knot looks like from the outsideDescribing what a knot looks like from the outside
QuaternaryQuaternary:: Consists of more than one polypeptideConsists of more than one polypeptide Like several completed knots glued togetherLike several completed knots glued together
40Levels of Protein Organization
41Examples of Fibrous Proteins
42Organic ChOrganic Chemistryemistry
Protein-folding DiseasesProtein-folding Diseases
Assembly of AA’s into protein extremely Assembly of AA’s into protein extremely complexcomplex
Process overseen by “Process overseen by “chaperonechaperone” molecules” molecules
Inhibit incorrect interactions between Inhibit incorrect interactions between RR groups as polypeptide growsgroups as polypeptide grows
Defects in these chaperones can corrupt the Defects in these chaperones can corrupt the tertiary structure of proteinstertiary structure of proteins
Mad cow disease could be due to mis-folded Mad cow disease could be due to mis-folded proteinsproteins
43Organic ChOrganic ChemistryemistryFour Classes of Organics:Four Classes of Organics:
4 -Nucleic Acids4 -Nucleic Acids
Polymers of nucleotidesPolymers of nucleotides
Very specific cell functionsVery specific cell functionsDNADNA ( (deoxyribonucleic aciddeoxyribonucleic acid)) Double-stranded helical spiral (twisted ladder)Double-stranded helical spiral (twisted ladder) Serves as genetic information centerServes as genetic information center In chromosomesIn chromosomes
RNARNA ( (ribonucleic acidribonucleic acid)) Part single-stranded, part double-strandedPart single-stranded, part double-stranded Serves primarily in assembly of proteinsServes primarily in assembly of proteins In nucleus and cytoplasm of cellIn nucleus and cytoplasm of cell
44Organic ChOrganic ChemistryemistryThe Nucleotides ofThe Nucleotides of
Nucleic AcidsNucleic Acids
Three components:Three components:
A phosphate group,A phosphate group,
A pentose sugar (ribose or deoxyribose), andA pentose sugar (ribose or deoxyribose), and
A A nitrogenous basenitrogenous base (4 kinds in DNA, 3 kinds in (4 kinds in DNA, 3 kinds in RNA, 3 common to bothRNA, 3 common to both
Nucleotide subunits connected end-to-end to Nucleotide subunits connected end-to-end to make nucleic acidmake nucleic acid
Sugar of one connected to the phosphate of Sugar of one connected to the phosphate of the nextthe next
Sugar-phosphate backboneSugar-phosphate backbone
45Nucleotides
46DNA Structure
47RNA Structure
48Organic ChOrganic Chemistryemistry
NoNoYesYesHelixHelix
Interprets genetic info; Interprets genetic info; protein synthesisprotein synthesis
Heredity; cellular Heredity; cellular control centercontrol centerFunctionFunction
Cell nucleus and Cell nucleus and cytoplasmcytoplasm
Chromosomes of cell Chromosomes of cell nucleusnucleusWhereWhere
Comparison of DNA & RNAComparison of DNA & RNA
Table 3.4Table 3.4
Mostly single strandedMostly single strandedDouble-stranded; Double-stranded; Pairing across strandsPairing across strandsStrandsStrands
Cytosine, guanine;Cytosine, guanine;adenine, adenine, uraciluracil
Cytosine, guanine;Cytosine, guanine;adenine, adenine, thyminethymineBasesBases
RiboseRiboseDeoxyriboseDeoxyriboseSugarSugar
RNARNADNADNAFeatureFeature
49Organic ChOrganic Chemistryemistry
Other Nucleic AcidsOther Nucleic Acids
ATP (adenosineATP (adenosine triphosphate) is composed of triphosphate) is composed of adenine, ribose, and three phosphatesadenine, ribose, and three phosphates
In cells, one phosphate bond is hydrolyzed – In cells, one phosphate bond is hydrolyzed – Yields:Yields:
The molecule The molecule ADPADP ( (adenosine diphosphateadenosine diphosphate))
An inorganic phosphate molecule pAn inorganic phosphate molecule pii
EnergyEnergy
Other energy sources used to put ADP and pOther energy sources used to put ADP and p ii back together againback together again
50ATP
51Organic ChOrganic Chemistryemistry
ReviewReview
Organic vs InorganicOrganic vs Inorganic
Functional Groups and IsomersFunctional Groups and Isomers
MacromoleculesMacromolecules
CarbohydratesCarbohydrates
LipidsLipids
ProteinsProteins
Nucleic AcidsNucleic Acids
Organic Chemistry
Ending Slide Chapter 03