CHM 25500 Final Exam Study Guide
CHM 25500 Final Exam Study Guide CHM 25500 - 001
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CHM 25500 - 001
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This 3 page Study Guide was uploaded by Gayatri on Saturday December 12, 2015. The Study Guide belongs to CHM 25500 - 001 at Purdue University taught by Christopher H Uyeda in Fall 2015. Since its upload, it has received 88 views. For similar materials see Organic Chemistry in Chemistry at Purdue University.
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Date Created: 12/12/15
CHM 25500 Final Exam Study Guide New material Chapter 10 Alcohols Alcohol a compound containing an OH hydroxyl group Thiol a compound containing an SH sulfhydryl group Alcohol and thiol nomenclature 0 Parent chain longest chain w the OH or SH group 0 Replace e at end of alkane 9 ol 0 Multiple alcohol groups diol triol etc o Thiols in alkane alkanethiol 0 Multiple thiol groups dithiol trithiol etc Physical properties 0 Polar I Engage in hydrogen bonding interactions I High boiling point relative to alkanes I Soluble in polar solvents like water I Acidity thiols gt alcohols Increases as ion size increases Deprotonation Metal alkoxides can be made from alcohols metalsmetal hydrides 0 Acid base reactions like CH3OH NaH 9 CHgO39 Na H2 gas 0 Oxidation reduction reactions like CH3OH Na 9 CHgO39 Na H2 gas Conversion to alkyl halides o Tertiary carbons undergo SNl 0 Secondary carbons undergo SNl or SN2 0 Primary carbons undergo SN2 0 Usually OH on the carbon molecule is a poor leaving group is made into a good leaving group with the help of a strong acid such as HCl I HCl protonates the alcohol making it a good leaving group charge on O Alternative methods of converting alcohols to leaving groups 0 PBI 3 I Only useful for primary and secondary unhindered carbons I SN2 mechanism somewhat like a double substitution reaction o SOClz I Additional base such as Et3N is also needed I Leaving group fragments into two pieces S02 and Cl39 0 Conversion to sulfonates I Good for SN2 reactions act like halides 1 Br I Sulfonate is a very stable molecule fragmentation does not occur with Cl39 Stabilized by resonance Alkyl sulfonates can react with nucleophiles 0 Useful for primary and secondary electrophiles o SN2 mechanism inversion of stereochemistry occurs Acidcatalyzed dehydration of alcohols to alkenes 0 Forms more substituted alkene o Tertiary and secondary alcohols undergo E1 mechanism 0 Primary alcohols undergo slow E2 mechanism because the base is weak 0 Done with H2SO4 heat creates alkene and water Oxidation reactions 0 Primary alcohols I Alcohol C3HgO9 Aldehyde C3H6O 9 Carboxylic Acid C3H6Oz 0 Secondary alcohols 39 Alcohol C3H80 9 Ketone C3H60 o Tertiary alcohols I No viable oxidation reaction because no protons left to remove Reagents of Oxidation Reactions 0 H2CrO4 chromic acid CI39O3 H2SO4 HzO I Primary alcohol 9 carboxylic acid I Secondary alcohol 9 ketone o PCC pyridinium chlorochromate CrO3 HCl pyridine I Primary alcohol 9 aldehyde I Secondary alcohol 9 ketone Chapter 11 Ethers and Epoxides Ether functional group containing an O bound to two C s Nomenclature 0 Select longest parent chain name OR group attached to it alkoxy Physical Properties 0 Ethers can accept H bonds from alcohols or water 0 Ethers are more soluble in water than alkanes but less than alcohols 0 BP and solubility in water ethanol gt dimethyl ether gt propane Preparation of ethers o Williamson ether synthesis SN2 substitution I Competing mechanism E2 elimination I Use less hindered electrophile alkyl halide to favor SN2 ether formation 0 Acid catalyzed addition of alcohols to alkenes I Markovnikov selectivity ether on more substituted carbon I Occurs with H and CH3OH similar to hydration reaction Epoxides 3 membered ring ethers 0 Very reactive due to ring strain Preparation of epoxides 0 From alkenes I Cycloalkene RCO3H 9 Cycloalkane with 3 membered ring RCOzH I Z alkene gives cis structure I E alkene gives trans structure 0 From intramolecular substitution I SN2 mechanism I NaOH deprotonates the H from OH and then 039 closes in on the other carbon forming an epoxide and kicking off Cl I Stereoselective OH and C must be anti and coplanar Trans reactants 9 trans products same for cis Ring Opening of Epoxides o SN2 substitution with anionic nucleophiles water I Less hindered carbon is favored I Stereochemistry is preserved o Acidcatalyzed opening with neutral nucleophiles H I In the case of achiral reactants ll racemix mix of enantiomers is produced depending on which side the O attacks on I Stereochemistry is preserved for the carbon that O doesn t attack the one with the original OH
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