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CHM 256 Lab Final

Purpose of the epoxidation lab To use an epoxidation reaction to synthesize cholesterol epoxide.
Epoxide C-O-C in a ring
Reaction of expoxidation lab MCPBA + cholesterol + OH2Cll2 ---> 3-chlorobenzoic acid + 5a,6a epoxycholestor-3-ol *Stereospecific
Why is the epoxidation reaction sterospecific Because of the alkene configuration preventing free rotation around the pi bond (only form trans -OH)
What are two ways to convert an alkene to an epoxide? 1. MCPBA/CH2Cl2 2. (1)Cl2/H2O, (2)NaOH/H2O
Structure of steroids 4 ringed
Principle component in gallstones cholesterol
Estrone Female sex hormone (C18H22O2)
Structural difference between a carboxylic acid and a percarboxylic acid Percarboxylic acid has an O between the carbon and alcohol substituent
Purpose of What's that Smell lab To synthesize a commercially important fragrance in 2 steps by using (2) a chemoselective reduction reaction and (2) a polymer supported reaction
What are the 8 notes of the olefactory spectrum? musky, fruity, green, marine, floral, spicy, woody, ambery
How does the structure for isoeugenol compare to methyl diantilis The same except one of the -o- groups in methyl diantilis is a -=- in isoeugenol
Chemoselectivity vs. Regioselectivity Chemo - selective reaction of one functional group in the presence of others; Regio-leads to the selective formation of one structural isomer
Carbonyl + NaBH4/ethanol ---> Replace carbonyl with alcohol in ketones & aldehydes; Won't react with esters; Pulls hydrogen off carboxylic acid
Carbonyl + LiAlH4 ---> Replace carbonyl with alcohol (Reduces every carbonyl functional group!)
Is methyl diantilis at room temperature liquid or solid? liquid
Use of polymer-supported reagents in organic chemistry has become much more widespread since the "explosive growth" in what field of chemistry? combinational
Who is credited for the invention of Methyl Diantilis and who did her work for? Paul Ochsner; Givaudan
Why would you add sodium bicarbonate to a reaction mixture during work up of a reaction? To neutralize and separate any acid in the crude product
Why would Amberlyst 15 be washed with methanol? To ensure purification, wash is with a solvent it is not soluble in
What is used in industrial preparation of methyl diantilis instead of Amberlyst 15? Convert the alcohol functional group to an ether using NaHSO4
What range indicates purity due to melting point? +/- 2 degrees
Purpose of Oxidation Aromatic lab Use an oxidation reaction to convert toluene to benzoic acid; Oxidation = KMno4/heat/H2SO4
What is a benzylic C-H bond? C-H bond adjacent to the benzene ring (Benzene - RH3)
Why do reaction occur preferentially at the benzylic position in aromatic compounds with an alkyl side chain? Resonance; benzine ring alone is resistant to reaction with reagents that normally attack alkanes
What is the brown solid formed as the oxidation of toluene proceeds? MnO2
What does an aromatic side chain have to have in order to be able to undergo oxidation to produce a carboxylic acid functional group? benzylic hydrogen
What are two aromatic substituents that are unchanged by conditions required to oxidize an alkyl side chain on the aromatic ring? halogen & nitro substituents
Purpose of esterification lab Synthesize benzocaine from p-aminobenzoic acid via an esterification reaction
Zwitterion An overall neutral molecule that has two separated and opposite formal charges within the molecule
Fischer esterification Conversion of a carboxylic acid and an alcohol to an ester
Functional groups present in benzocaine and novocaine (3) Benzene ring, ester, amine
What substance could potentially contaminate dry benzocaine product but wouldn't show up on a TLC plate under UV light? Na2CO3
What is the function of benzocaine in commercial products? anesthetic because slight numbing capabilities
Purpose of calcium lab To synthesize a calcium channel blocker by using 3 small organic molecules (benzaldehyde, ethyl acetoacetate, urea)
What are calcium channel blockers and how do they function? Antihypertensives that inhibit movement and binding of calcium ions leading to a relaxing of vascular smooth muscles and reduction of vascular resistance
How have we monitored the progress of reactions while they're happening? TLC
What substance is used as the solvent for the Bignelli reaction in the calcium blocker experiment? ethanol
What is the max height at which the solvent should condense during reflux and why? Halfway up the condenser or all of the solvent may not run back into the reaction flask
Purpose of aldol lab Determine whether or not the temperature affects the reaction pathway for a "green" aldol reaction
In the aldol lab which product was heated and which was at room temperature? Heated: condensation product (double bond); Room temp: aldol product (-OH)
Why must samples of 2-acetylpyridine be kept in a hood? It can cause respiratory tract infection if inhaled via gases and is flammable
What species are involved in the key C-C bond forming step of an acid-catalyzed aldol reaction? enolate C woul dact as a base
What is the difference between aldol addition and aldol condensation Aldol addition --> -OH; -H20 aldol condensation --> C=C
4 reactions that form C-C bonds aldol, grignard, biginelli, wittig
Crossed aldol reaction Two different carbonyl compounds react
_________ carbonyl containing compounds would not undergo an aldol reaction under basic conditions symetrical
Aldol reaction requires aldehyde or unsymmetrically substituted ketone (2) + base
Equilibrium constant is large when... products are favored over reactants
How to calculate Rf values distance spot moved / distance solvent moved
Why was the aldol reaction considered "green"? Used water
Purpose of EAS to Synthesize p-Nitrochlorobenzene lab 1. Synthesize p-nitrochlorobenzene from chlorobenzene using an EAS reaction; 2. use flash column chromatography to purify the synthesized p-nitrochlorobenzene
Electrophilic aromatic substitution reaction There is substitution of an electrophile for a hydrogen on an aromatic ring
Why couldn't you use acetone in the p-Nitrochlorobenzene lab? Acetone and nitric acid form an explosive material
What electrophile is generated by the reaction of nitric acid and sulfuric acid? NO2+ (nitronium ion)
Why can't p-nitrochlorobenzene be made in the presence of a lewis acid and catalyst such as FeCl3 or AlCl3? Nitro on benzene is too strong of an e- with drawing group and would form meta if you were able to get it to react.
What is the rate determining step and is it endo or exo thermic in electrophilic aromatic substitution? Attack of strong electrophile by the weak nucleophilic pi electrons of the aromatic ring to form the carbocation intermediate. Endothermic due to high activation energy needed to break up aromaticity
NO2 is ortho, meta, or para reacting? meta
Activating vs deactivating substituents on benzene ring in EAS Activating/(o/p): NH2, NHR, OH, OR (lone pairs, alkyl, aromatic, halogens(meta)); Deactivating/meta: CCl3, NO2, NH3,+, CN (fully substituted, carbonyl w/o lone pairs)
How to add nitro group to benzene HNO3/H2SO4
Created by: jkmccord11