ORGANIC CHEMISTRY BASICS

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Organic Chemistry Basics - alkanes, alkenes, alkynes, naming, functional groups, structural isomers, and optical isomers

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Organic Chemistry Basics

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The next slide is a quick promo for my books after which the presentation will begin Thanks for your patience! Walt S. Wsautter@optonline.net More stuff at: www.wsautter.com

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Books available at: www.smashwords.com www.amazon.com Walt’s Books for Free!

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All organic compounds consist of carbon and hydrogen . Many also contain oxygen and nitrogen Other elements may also be present. Phosphorous, halogens and/or metals Most compounds are composed of carbon chains bonded with hydrogen

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H H H H H | | | | | H - C – C – C – C – C – H | | | | | H H H H H A carbon / hydrogen chain (organic) H H H H H | | | | | H - C – C – C – C – C – O - H | | | | | H H H H H A carbon / hydrogen chain containing oxygen

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Carbon can make four (4) bonds Hydrogen can make one (1) bond Oxygen can make two (2) bonds Nitrogen can make three (3) bonds Sulfur can make two (2) bonds Halogens can make one (1) bond | – C – | H – - O - – N – | - S – Cl -

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| – C – H | – C = O | C N Carbon can make single, double or triplebonds Hydrogen can make only single bonds Oxygen can make single or double bonds – C = O | | | C – O - C | |

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Nitrogen can make single, double or triplebonds Sulfur can make single or double bonds Halogens can make only single bonds H– N – H | H – C = N | C N | | - C – S – C - | | – C = S | | - C - Br |

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Naming Organic Compounds Meth = 1 C Eth = 2 C Prop = 3 C But = 4 C Pent = 5 C Hex = 6 C Hept = 7 C Oct = 8 C Non = 9 C Dec = 10 C Study this Slide and then click here To continue

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Aliphatic Hydrocarbons Alkanes – All single bond between carbons (name ends in “ ane ”) Alkenes – contains double bonds between carbons (name ends in “ ene ”) Alkynes – contains triple bonds between carbons (name ends in “ yne ”)

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Naming hydrocarbons starts with selecting the longest Chain (even around corners). H H H H H H | | | | | | H - C – C – C – C – C – C - H | | | | | H H H H H - C - H | H - C – H | H 7 C c h a i n Not 5 C chain Name starts with “hept” (7C) All single bonds Name ends with “ane” Heptane | H

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H H H H H H | | | | | | H - C – C – C – C – C – C - H | | | | | H H H H H - C - H | H - C – H | H | H Naming the Side Chain Side Chain

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H- C- C -C - H H H | | | H H H | | | H H H H | | | | H H H H | | | | H- C- C -C -C - -C - H H H | | -C - H H H | | C H- -H | Methyl CH 3 Ethyl C 2 H 5 Propyl C 3 H 7 Butyl C 4 H 9 Some Common Side Chains

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H H H H H H | | | | | | H - C – C – C – C – C – C - H | | | | | H H H H H - C - H | H - C – H | H | H -C - H H H | | Methyl Methyl Heptane But where is the methyl Group attached?

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H H H H H H | | | | | | H - C – C – C – C – C – C - H | | | | | H H H H H - C - H | H - C – H | H Count from the Short end of The chain Methyl group is attached to the third carbon thus 3 methyl heptane 3 methyl heptane | H

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H H H H H | | | | | | H - C – C – C – C – C – C - H | | | | | H H H H H - C - H | H - C – H | H -C - H H H | | | H Two side chains The first methyl group is on the second Carbon counting from the short end! The second methyl group is on the fifth Carbon counting from the short end! 2, 5 dimethyl heptane

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Alkenes (Double bonds) H H H H H H | | | | | | H - C – C – C – C = C – C - H | | | | H H H H | H A six Carbon chain – “hex” Alkene – ends in “ene” Double bond on second Carbon From shortest end of chain 2 hexene

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H H H H H | | | | | | H - C = C – C – C – C – C - H | | | H H H - C - H | H - C – H | H -C - H H H | | | H 2, 5 dimethyl 1 heptene Alkene with two side groups

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H H H H H H | | | | | | H - C – C – C – C – C – C – C C-H | | | | | H H H H H - C - H | H - C – H | H | H Longest chain 8 Carbons (oct) 2 Carbon Side chain (ethyl) on C atom 4 Triple bond on C atom 1 (“yne”) Alkynes (triple bond) 4 ethyl 1 octyne

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Alkynes (triple bonds) Alkenes (Double bonds) Alkanes (Single bonds) C n H (2n +2) C n H 2n C n H (2n -2) General Formula C 3 H 8 C 3 H 6 C 3 H 4 Propane Propene Propyne

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| O -H – C = O | O | Hydroxyl Ester Linkage – N – H | H Amine Common Organic Groups

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– C = O O -H | Carboxyl – C = O | Carbonyl | | - C – O – C - | | Ether Linkage Amide – C = O | N – H | H C

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– C = O | Carbonyl | | - C – O – C - | | Ether Linkage + = – C = O | O | Ester Linkage Some functional groups are combinations of smaller functional groups

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| O -H Hydroxyl + – C = O | Carbonyl = – C = O O -H | Carboxyl – N – H | H Amine – C = O | Carbonyl + = – C = O | – N – H | H C Amide

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Compounds Containing Functional Groups Alcohols O-H End in “ol” -C - H H H | | C H- -H | Ethyl C 2 H 5 O-H Ethyl Alcohol Ethanol Common name Grain alcohol R –OH R = a Carbon/ Hydrogen chain

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ketones – C = O | End in “one” Methyl ethyl ketone Butanone 2 butanone is incorrect Since counting from either end would put the carbonyl On the second Carbon R– C = O | R R = a Carbon/ Hydrogen chain -C - H H H | | C = O -C - H H | | C H- -H | H Compounds Containing Functional Groups

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Aldehydes – C = O | H End in “al” -C - H H H | | C=O H - Ethyl Aldehyde Ethanal Common name Acetaldehyde R – C = O | H R = a Carbon/ Hydrogen chain Compounds Containing Functional Groups

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Acids – C = O | O -H End in “oic” -C - H H H | | | Acetic Acid Ethanoic Acid Common name Vinegar R– C = O | O -H R = a Carbon/ Hydrogen chain C = O O -H Compounds Containing Functional Groups

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Structural Isomers Same formula but different arrangement of atoms H H H H | | | | H H H H | | | | H- C- C -C -C -H Butane C 4 H 10 H H H | | | H | H | | | H- C- C -C -H Methyl Propane C 4 H 10 H – C – H | H

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Propanone Propanal

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Chiral Carbons

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Out of screen Into screen Molecules Cannot be Superimposed!

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Cis and Trans Isomers cis-butenedioic acid (maleic acid) trans-butenedioic acid (fumaric acid) Double bond

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Aromatics Aromatics are compounds that contain a benzene ring as part of their structure C 6 H 6

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Delocalized Electron cloud Resonance structure

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Different symbols for the Benzene Ring

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Aspirin Some Common Aromatics

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Cyclics and Aromatics At first glance they look the same but aren’t C 6 H 6

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