CH04_2_ - Overview of Carbon Chemistry Versatilit of Carbon...

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Unformatted text preview: Overview of Carbon Chemistry Versatilit of Carbon tility Hydrocarbons Isomers Structural Geometric Stereoisomers Overview of Carbon Chemistry Functional Groups Hydroxyl Carbonyl Carboxyl Methyl Amino Thiol Phosphate Ester Bio 230, Summer 2010, Ch 4, Page 1 Organic Chemistry Most chemicals in living organisms contain carbon organisms contain carbon Organic Chemistry is the study of molecules containing a ca carbon skeleton H, N & O are the other main elements in organic compounds Fig. 4-3: Valences of H, O, N and C 4- Valence: Number of electrons needed to Number of electrons needed to fill fill the outer-shell outer- Bio 230, Summer 2010, Ch 4, Page 2 Organic Chemical Diversity Of all the elements, carbon allows the most diverse chemical structures Carbon forms covalent bonds because it is not very electronegative Organic Chemical Diversity Carbon’s four valence Carbon four valence electrons electrons allow carbon to make the equivalent of four covalent bonds Carbon forms the straight, branched, and ringed skeletons of organic compounds Bio 230, Summer 2010, Ch 4, Page 3 Fig. 4-2: The Simplest Hydrocarbons 4- Organic Chemical Diversity Sizes range from one carbon Si (CH4) to thousands (DNA, proteins) Bio 230, Summer 2010, Ch 4, Page 4 Hydrocarbons Contain just carbon and hyd h drogen atoms Tend to be non-polar (hydronon(hydrophobic); don’t dissolve in water water Simplest hydrocarbon is methane: CH4 Fig. 4-2: The Simplest Hydrocarbons 4- Bio 230, Summer 2010, Ch 4, Page 5 Methane Ethane Bio 230, Summer 2010, Ch 4, Page 6 Ethylene Fig. C4-4a: More Complex Hydrocarbons C4- Bio 230, Summer 2010, Ch 4, Page 7 Fig. C4-4b: More Complex Hydrocarbons C4- Butane Bio 230, Summer 2010, Ch 4, Page 8 Isobutane Fig. C4-4c: More Complex Hydrocarbons C4- Bio 230, Summer 2010, Ch 4, Page 9 Fig. C4-4d: More Complex Hydrocarbons C4- planar Cyclohexane Bio 230, Summer 2010, Ch 4, Page 10 Hydrocarbons More complex hydrocarbons include fossil fuels Waxes, fats, and phospholipids contain large hydrocarbon tails hydrocarbon “tails” Fig. 4-5a: 4Fats Have Hydrocarbon Tails C= H= O= Bio 230, Summer 2010, Ch 4, Page 11 Fig. 4-5b: Adipose (Fat) Cells 4- LM TEM Isomers Isomers have the same chemical chemical formula, but different structures In structural isomers some covalent covalent partners are different Bio 230, Summer 2010, Ch 4, Page 12 Fig. 4-6a: Structural Isomers 4- C4 H10 Fig. 4-4c: Structural Isomers 4- C4 H8 Bio 230, Summer 2010, Ch 4, Page 13 Isomers In geometric isomers the covalent partners are the same, but the geometry at one or more double bonds is different cis, trans Fig. 4-6b: Geometric Isomers 4- cis X trans X X Bio 230, Summer 2010, Ch 4, Page 14 X Fig. 49-12a: 11-cis-Retinal 4911- C C Fig. 49-12b: All-trans-Retinal 49All- H C C Bio 230, Summer 2010, Ch 4, Page 15 Isomers In stereoisomers, one or more In stereoisomers one or more asymmetric carbons have “mirror“mirror-image” geometry D, L amino acids, sugars Fig. C4-6C: C4Stereoisomers of Alanine Al L Asymmetric Carbon D Bio 230, Summer 2010, Ch 4, Page 16 Isomers In enantiomers, all In enantiomers all asymmetric carbons have “mirror“mirror-image” geometry, making the both molecules mirror images of each other mirror Fig. 4-7: Enantiomers 4Carboxyl Group (COOH) Bio 230, Summer 2010, Ch 4, Page 17 L-Dopamine: A Neurotransmitter Fig. 2-18: Synapse 2- L-Dopamine Bio 230, Summer 2010, Ch 4, Page 18 Functional Groups Add unique characteristic to organic molecules Mainly hydrophilic Functional Groups Formula Group Hydroxyl Example Ethanol (Ethyl Alcohol) Name of Compounds -OH Alcohols (not OH– Hydroxide) HH H-C-C-OH HH Bio 230, Summer 2010, Ch 4, Page 19 Functional Groups Group Formula Methyl Name of Compounds -CH3 H H-C-OH H Example Methanol (Methyl Alcohol) Functional Groups Group Formula Ethyl Name of Compounds -CH2-CH3 Example Ethanol (Ethyl Alcohol) HH H-C-C-OH HH Bio 230, Summer 2010, Ch 4, Page 20 Functional Groups Group Formula Carbonyl -C=O Functional Groups Group Formula Carbonyl -C=O H Example Propanal Name of Compounds Aldehydes HH O H-C-C-C H HH Bio 230, Summer 2010, Ch 4, Page 21 Functional Groups Group Formula Carbonyl O -C-C-C- Example Acetone Name of Compounds Ketones HOH H-C-C-C-H HH Functional Groups Group Formula Carboxyl O -C OH Example Acetic Acid Name of Compounds Organic Acids Acids or Carboxylic Acids H O H-C-C OH H Non-Ionized Bio 230, Summer 2010, Ch 4, Page 22 Functional Groups Group Formula Carboxyl Example Acetic Acid -C O OH Name of Compounds Organic Acids Acids or Carboxylic Acids H O H-C-C O – H+ H Ionized Functional Groups Group Formula Ester O -C-O- Example Acetoacetate Name of Compounds Esters HO H O H-C-C-O-C-C OH H H Bio 230, Summer 2010, Ch 4, Page 23 Functional Groups Group Formula Amino -NH2 Name of Compounds Organic Bases Bases or Amines H O H Glycine C-C-N H HO H Example (an amino acid) H+ Non-Ionized Functional Groups Group Formula Amino -NH2 Name of Compounds Organic Bases Bases or Amines H H O Glycine C-C-N+-H HO H H Example (an amino acid) Ionized Bio 230, Summer 2010, Ch 4, Page 24 Functional Groups Group Formula Name of Compounds Sulfhydryl -SH Thiols Example Ethanethiol HH H-C-C-SH HH Functional Groups Group Formula Phosphate -PO4 Name of Compounds Organic Phosphates O Glycerol – Phosphate H-C-C-C-O-P-O H H H O– Example HO OH H Bio 230, Summer 2010, Ch 4, Page 25 Functional Groups HH HH Ring Ring H’s not shown HH Steroids H H H H H H H H H H H HH HH Ri H’ Ring H’s shown Estrone Bio 230, Summer 2010, Ch 4, Page 26 HH Testosterone Bio 230, Summer 2010, Ch 4, Page 27 ...
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