Download DAT OChem Notecards. and more Exams Dentistry in PDF only on Docsity!
DAT OChem Notecards
tBuOK + R-NH-R -->? - ✔tBuOH + R-N-R K+ Phenol solubility in water - ✔insoluble due to very large non-polar ring Use _____ to extract acids Use _____ to extract bases - ✔basic conditions acidic conditions Ortho and para isomers use what separation techniques? - ✔recrystallization column chromatography Iodoform reaction - ✔ carboxylic acid and phenol proton acidity - ✔carboxylic acid protons are more acidic Anhydride formation - ✔ Acidic Epoxide conditions - ✔attacks more sub Basic epoxide conditions - ✔attacks less sub Naming bicyclic compounds - ✔start at bridge base and number longest side first 30% enantiomeric excess means ____ - ✔70% thats left is racemic How many monochlorinations of 2-methylbutane can occur? include stereoisomers - ✔ 6
UV spectroscopy - ✔Transitions between electron energy levels Does LAH reduce double bonds? - ✔No Electrophilic reactions usually involve _____ - ✔alkenes and alkynes Electrophilic sub is undergone by _____ - ✔aromatics Enamine reaction - ✔ Imine formation - ✔ Aldehyde in dilute acid/base does the _______ - ✔aldol condensation How to determine which CO2 will be lost - ✔Look for beta keto CO2 (2C's away from carbonyl) LDA structure and function - ✔Large hindered base; abstracts proton from most accessible hydrogen (not like NaOH which abstracts the most acidic) Henderson Hasselbach equation - ✔pH = pKa + log (salt/acid) Benzaldehyde Formaldehyde Aldol condensation? - ✔Cannot undergo aldol condensation because there is not an alpha hydrogen O/P directors - Activate, electron donating M directors - deactivate, electron withdrawing - ✔OH, CH3, OCH3, NH2, NO, Halogens (exception) CN, SO3, COOH, CF3, aldehyde, N+, ketone, NO
Excess D2O with Carbonyl and catalytic DCl - ✔Abstracts alpha hydrogens and replaces with D Acetoacetic ester synthesis - ✔ Another function of H2 w. Pt - ✔Opens small rings like cyclopropane Reactivity of the Halogens in radical rxns - ✔F > Cl > Br >I SN1 vs SN2 - ✔ Which carbon is missing an OH in DNA - ✔Carbon 2 Nitrogenous bases are located where on DNA - ✔inside the helix Stability and UV light - ✔more stable the compound (more resonance etc...) the longer the wavelength More stable = longer wavelength When there are two longest chains _____ - ✔take the one with the more substituents Amines and solubility - ✔Amines larger than 3 carbons will not be water soluble Protonation allows the amine to be soluble Allenes chirality - ✔Allenes are chiral even though there is no sp3 carbon Cyclohexane w. NBS and ROOR - ✔Adds Br to allylic position (most substituted if necessary) Different names of reactions - ✔Alkenes: Electrophilic addition Alkanes: Radical sub
Esters: Nucleophilic acyl sub Ketones: Nuc addition Aromatics: Electrophilic sub Cumulated diene - ✔ pyrrole - ✔ NaNH2 reaction - ✔E2 reaction HgSO4 - ✔Turns triple bond into carbonyl NaBH4 vs LAH - ✔NaBH4 only will reduce ketones to secondary alcohols and aldehydes to primary alcohols LAH will reduce everything Mutarotation - ✔Mutarotation is the change in the optical rotation because of the change in the equilibrium between two anomers, when the corresponding stereocenters interconvert. Cyclic sugars show mutarotation as α and β anomeric forms interconvert. Non-reducing sugars - ✔sucrose doesn't have hemiacetal group D-Sugar - ✔CH2OH group is on top
- Tollens and benedicts tests - ✔Mutarotates and is hemiacetal Azide reactions - ✔ Ester + Base = - ✔Claisen condensation
CuCN, CuCl, CuBr, KI, BF4 will replace with anions H3O+ and heat will place an OH Dieckman condensation - ✔Remove H and Ethoxy Equivalent proton splitting - ✔do not split chlorination of napthalene - ✔adds to adjacent carbons on one ring (only 1 at a time tho) Jones reagent - ✔Chromium based oxidizing agent Vinylic protons - ✔not acidic Flouridation propagation steps are very _____ - ✔exothermic Frequencies - ✔Conjugation decreases frequency triple > double > single in terms of vibration frequencies UV absorption (THINK COLOR) - ✔More stable = more color Conjugated = most stable In order for the molecule to give a signal on IR it must have a _____ - ✔dipole S and O nucleophilicity - ✔S is larger and electrons less tightly held than O therefore it is more nucleophilic Cyclohexene treated with H3O+ - ✔OH adds Cleavage - ✔O3 does not place OH upon cleavage KMnO4 does place OH
NBS with alkene - ✔removes allylic H and places Br Diazomethane use - ✔Forms 3 membered ring Heat of hydrogenation is smallest when _______ - ✔compound is stable LDA will remove the _______ - ✔most acidic proton How to get a trans alkene - ✔use Na with NH3 to get trans and H2 lindlar to get cis Aldhyde/ketone and alkyne acidity - ✔Aldehyde/ketone is more acidic Ester saponification - ✔ Baeyer villiger rxn - ✔
