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Organic Chemistry I

by: Corbin Crist DDS

Organic Chemistry I CHEM 3750

Corbin Crist DDS
GPA 3.81

Elke Schoffers

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Elke Schoffers
Class Notes
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This 4 page Class Notes was uploaded by Corbin Crist DDS on Wednesday September 30, 2015. The Class Notes belongs to CHEM 3750 at Western Michigan University taught by Elke Schoffers in Fall. Since its upload, it has received 28 views. For similar materials see /class/216967/chem-3750-western-michigan-university in Chemistry at Western Michigan University.


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Date Created: 09/30/15
Fall 07 Classes of Organic Compounds 1 Are defined by functional groups FGs 3 CHEM 3750 Organic Chemistry I Prof Schoffer s WMU Hydrocarbons only contain C H Compounds containing oxygen 0 Compounds containing nitrogen N Class FG Description Examples Abbrev iation 1 Hydrocarbons 11 Alkanes R H Contain only carbon methane CH4 ethane CH3 CH3 and hydrogen only propane CH3 CH2 CH3 butane single bonds pentane hexane cyclopentane cyclohexane Alkyl group R Alkyl group R group methyl CH3 ethyl CH2CH3 R abbreviation for H alkyl group 12 Alkenes Contain CC double ethene ethylene CH2CH2 propene bond propylene CH3CHCH2 cis trans isomers 2 butene possible 13 Alkynes Contain CEC triple ethyne H CEC H acetylene propyne bond HCECCH3 14 Aromatic Hydrocarbons Ar 3 CC in a 6 34 Arenes membered ring H H separated by C C benzene O CH bonds Ar Aryl group O phenyl group 2 Organic Compounds Containing Oxygen 21 Alcohols R OH Contain hydroxyl methanol CH3OH ethanol CH3 CH2 group OH H 22 Ethers R O R Contain ether C O C dimethyl ether CH3 O CH3 R O R bond O O CHS cyclohexyl methyl ether 23 Aldehydes amp Ketones Both contain carbonyl H group C20 C formaldehyde H H Aldehyde El 9 Rp i ethanal acetaldehyde HSC C H Ketone 9 methyl ethyl ketone 2 butanone Rp R39 O I Hac CHf CH3 Fall 07 CHEM 3750 Organic Chemistry I Prof Schoffer s WMU Class FG Description Examples Abbrev iation 24 Carboxylic Acids RCOOH Carbonyl C20 9 RC0 H h drox 1 OH rou 0 o 2 y y g p ethanoic acid acetic acid H30 OH ll CH COOH CH CO H R C OH 3 3 2 butyric acid butanoic acid CHSCHZCHZCOOH smell of rancid butter 25 Carboxylic Acid Derivatives 251 Acid chlorides El El 0 R 039 acetyl chloride H30 0 252 Esters El El 0 Fl OR methyl acetate H30 OCHS 253 Amides El El RANH acetamide HSC C NHZ 3 Organic Compounds Containing Nitrogen 31 Amines R NH2 All amines are basic methylamine Hsc NHz R NH R Fl lil R39 R 32 Amides El Amino group next to 9 A carbon 1 rou 0 R O NH y g p N methylacetamide H30 NHCH3 ll Rp NHR39 3 Rp NRIRII 33 Nitriles R CEN Contains a CEN triple acetonitrile Hsc CEN R CN bond benzonitrile CHEM 3750 ARROWS ORGANIC CHEMISTRY I Fall 07 HANDOUT Arrows Chemists use arrows as symbols in chemical equations straight arrows in between structures and as a bookkeeping symbol in mechanisms to show redistribution of valence electrons curved arrows STRAIGHT Straight arrows are placed in between reactants and products to represent a chemical reaction reversible irreversible AB AB A AB QiCIQI E gt C C B Usually describes irreversible reactions however it can also be used if an equilibrium exists that is shifted to the product side The number of reactants and products can vary Used for reversible reactions indicating that an equilibrium exists between reactants and products C D doubleheaded arrow is only used inbetween E structures Ezwi lt gt e 39C3e The double headed arrow is used as a symbol for resonance only between contributing structures All atoms remain in the same position while only J39IZ and non bonding valence electrons are redistributed CUR VED A Curved arrows move twg electrons Fishhook arrow moves gm electrom J Curved arrows are used as symbols to explain mechanisms electron pushing and as bookkeeping tools to track the movement repositioning redistribution of valence electrons This formalism helps to follow bond breaking and bond making A MORE DETAILED DISCUSSIONABOUT CURVED ARROWS mr Ho C l H H gt H o H O l l i m gt Ar B r Cl Cl gt c c This arrow always moves two electrons It is a symbol to show the redistribution of valence electrons and indicates the repositioning of an electron pair bonded or non bonded from its origin the tail to its destination the head The direction of the arrow between neutral and or charged species is very important and results by various combinations from the following W Electronrich center W Negative charge W Anionic center W Electronpoor ldeficient center W Positive charge W Cationic center W Lewis base W Lewis acid W Electronpair donor W Electronpair acceptor W Nucleophile Nu39 W Electrophile E s H EH THIS IS WRONG The proton has NO electrons to move iso H H HerxniH CORRECT 3 H H H H H63 igi H gt H illigH or H ii H not H igi H H H H H also correct NOT correct Charges The positioning of charges is important Please take special care for their placement In the example above the proton has received an electron from nitrogen that cancels the charge on hydrogen Nitrogen however is sharing electrons with the fourth hydrogen and therefore gave up one electron with the fourth bond Thus nitrogen carries the positive charge ADDITIONAL EXAMPLES Practice these examples by confirming the correct arrow direction and keeping track of charges Realize that typically the curved arrow can move from an electronegative atom to a more electropositive atom in between two species bond formation See examples 12 Cl 0 are more electronegative than C HOWEVER the curved arrow can also move away from the electropositive atom to the more electronegative atom within one species bond cleavage See examples 3 4 5 Br 0 I are more electronegative in comparison with adjacent atom and M have higher affinity for electrons DRAW complete Lewis structures for L keen track of all charges follow octet rule and pay attention to the type of arrows used and their direction CH CH 1 CH3 H 3 3b s 9 I I Hac CIQQIQI Hac c CI H30 El 39 HsC IEI CH3 CH3 CH3 CH3 2 CH3 4 CH OH A H3 3 I 3 HBO 36gt Iclgt H H3C H HsC i Qij H gt H3C Ce ICID H H3 H CH3 H H3 H3 H 5 H I l gt He 9391 I


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