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Organic Chemistry 231 Week 3 Notes

by: Jernelle John

Organic Chemistry 231 Week 3 Notes CHEM 231

Marketplace > University of Maryland > Chemistry > CHEM 231 > Organic Chemistry 231 Week 3 Notes
Jernelle John
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These are notes from week 3 of organic chemistry 231.
Organic Chemistry 1
Dr. Monique Koppel
Class Notes
Chemistry, Organic Chemistry, Science, orgo, Orgo I
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This 5 page Class Notes was uploaded by Jernelle John on Sunday September 18, 2016. The Class Notes belongs to CHEM 231 at University of Maryland taught by Dr. Monique Koppel in Fall 2016. Since its upload, it has received 9 views. For similar materials see Organic Chemistry 1 in Chemistry at University of Maryland.

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Date Created: 09/18/16
Monday, September 19, y Week 3 Notes Organic Chemistry ­ To stabilize a negative charge on an acid (A­) • negative charge should be on the most electronegative atom • negative charge should be on the larger atom • negative charge should be on the orbital with the most s character (sp orbital has  more s character (50% s character) than sp2 (33% s character) or sp3 (25% s  character) orbitals • inductive effect­ other atoms besides the atom with the negative charge apart of the compound that are more electronegative are more stable than atoms on apart  compound that are less electronegative ­ Lewis acid­base reactions­ a reaction which contain two reactants (the acid and the  base) and form one product through covalent bonding • can be protic (proton donor) or anti­protic (proton acceptor) ­ Brønsted­Lowry reactions are always protic (proton donors) • Lewis Acid­ a species that can form a new covalent bond by accepting a pair of  electrons and gaining a negative charge • Lewis Base­ a species that can form a new covalent bond by giving away a pair of  electrons and gaining a positive charge ­ Determining the equilibrium of an acid base reaction • compare the pKa values of the acid and the conjugate acid ­ the acid with the larger pKa value is the weaker acid • equilibrium will always favor the side of the weaker acid ­ Determining the Strength of an acid­ A stronger acid is 1 Monday, September 19, y • the larger compound • the more electronegative compound • compound with hybridization • acid that is influenced by the inductive effect­ pulling electrons towards one side of  a compound using other atoms apart of the compound • acid with more resonance ­ IUPAC Naming of a compound • determine the longest Carbon chain ­ naming alkanes (single bonded carbon chain):  • methane (1 carbon),  • ethane (2 carbon),  • propane (3 carbon),  • butane (4 carbon),  • pentane (5 carbon),  • hexane (6 carbon),  • heptane (7 carbon),  • octane (8 carbon),  • nonane (9 carbon),  • decane (10 carbon) • make a list of the substituents/alkyles from that carbon chain ­ alkyles­ side groups that come off from the alkane group • methyl (1 carbon) 2 Monday, September 19, y • ethyl (2 carbon) • propyl (3 carbon) • butyl (4 carbon) • pentyl (5 carbon) • hexyl (6 carbon) • heptyl (7 carbon) • octyl (8 carbon) • nonyl (9 carbon) • decyl (10 carbon) ­ alphabetize the carbon chain adding the number at which carbon from the main  carbon chain the alkyl group comes off from • put it all together!­ starting with the alphabetized alkyl groups  and ending with the alkane name • ex. ­ longest chain contains 5 carbons (pentane) ­ chain contains 2 substituents (2 methyl groups) ­ Finale Name: 2,3 dimethylpentane • “di”methyl because there are 2 methyl groups ­ tri­ before three of the same alkyl groups ­ tetra before four of the same alkyl groups • Another example ­ longest chain contains 8 carbons (octane) 3 Monday, September 19, y ­ chain contains 2 substituents • one methyl group • one ethyl group • e comes before m ­  Final Name: 5­ethyl­2­methyloctane • Unsaturation­ compounds that contain a double bond and/or triple bond ­ if the carbon chain contains a double bond than it is a alkene group and the  parent chain will end in ene (methene, ethene, propene, butene…) ­ if the carbon chain contains a triple bond than it is an alkyne group and the  parent chain will end in yne (methyne, ethyne, propyne) ­ ex.  • longest chain has 6 carbons ­ hexene • the double bond is contained on the 3rd carbon ­ 3­hexene • the substituent is on the 3rd carbon ­ methyl • Full Name: 3­methyl­3­hexene • cyclo carbon chains­ carbons that are connected on all sides ­ add cyclo win front of alkane or alkene ­ the cycloalkane on the right is cyclohexane ­ Non­IUPAC naming aka common naming 4 Monday, September 19, y • akyl groups ending in “iso” ­ an akyl group that contains a carbon chain with two  methyl groups on each side of it (Y shaped) • ex. non­IUPAC naming: 4­isopropylheptane • IUPAC naming: 4­ethyl­(1­methyl) heptane • alkyl groups ending in “sec” ­ carbon substituent with a methyl group on one side and ethyl group on the other • ex. non­IUPAC naming: 5­secbutylnonane • IUPAC naiming: 5­propyl (1­methyl) nonane • alkyl groups ending in “tert” ­ contain three methyl groups off of the first carbon substituent ­ ex. non­IUPAC naming: 4­t­butlyoctane ­ IUPAC naming: 4­ethyl (1,1 dimetyl) octane 5


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