CHEM 241 Key Terms from All Lectures PDF

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CH 1: Principles of Bonding NOTES

HW

- electronic and molecular structure, electronegativity - octet rule - nucleophile, electrophile - structural formula, formal charge, lewis structure - resonance structure - major contributions influence - acids and bases - arrhenius, bronstead-lowry, lewis

- line structure - resonance forms - pH - electron flow using curved arrows - electrophile, nucleophile, resonance

CH 2: Molecular Orbital Theory NOTES

HW

- atomic structure, atomic orbitals - linear combination of atomic orbitals, pi bonds, sigma bonds - hybridized orbitals, hybridization - geometric implications of hybridization - cis (Z), trans (E) - geometric isomers - molecular polarity, dipole moments - intermolecular forces - solubility effects - functional groups - alkanes, alkenes, alkynes, aromatic hydrocarbons, alcohols, ethers, aldehydes and ketones, amines, carboxylic acids, nitriles

- electron configuration - energy level - hybridization - geometric isomers - dipole moments - boiling points, intermolecular forces - soluble in water - draw structures - functional groups - molecular overlap

CH 3: Alkanes NOTES

HW

- Physical properties - molecular formula - nomenclature - IUPAC naming system - conformational analysis - newman projections - isomerism - ring strain - cyclohexane - bicyclic molecules

- number of isomers - name compounds - draw eclipses and staggered, energy changes - spiro, bicyclo

CH 4: Chemical Reactions NOTES - determining reaction mechanisms - chlorination - radical stability - activation energy - transition structures; endothermic, exothermic - reaction coordinate - bond dissociation energies - reaction rates - halogenation -- free radical halogenation, allylic halogenation - NBS, NCS - chlorination - Hammond postulate - reactive intermediates - carbocation, hyperconjugation, carbanion, Carbenes

HW - radical radical recombination - stability order - reaction-energy profile - activation energy - delta G - intermediate radicals - monobromincation - bond energy - NBS, CCl4, hv - NaOH -

CH 5: Stereochemistry NOTES

HW

- chirality, chiral center, enantiomer - nomenclature -- R vs S - bond breaks, phantom atom - Fischer projection formula - optical determination of enantiomeric composition - racemic mixtures - diastereomers, Isomer chart

- same, enantiomer, diastereomer - stereogenic center - configurations of chiral centers - line structures from fischer projections - [a]d25 - racemic mixture reactions

CH 6: Alkyl Halides SCHEMATIC DIAGRAM

NOTES - alkyl, vinyl, aryl - nomenclature, structure and properties - nucleophilic sub of alkyl halides - substitution, elimination, leaving group, SN2, SN1 - nucleophile, product, functional group - Steric hindrance, nucleophilicity, solvent effects - THF, acetone, DMF, oxonium ammonium, sulfonium, leaving group - NaCN / DMF; NAI, acetone/heat; THF/heat - SN1 rearrangements - MeOH/heat - secondary alkyl halides - NaSCH3; Br2, hv; LiOH, THF; SOCl2, DMF heat - E1, E2 - chirality in reactions - reduction

- SN2, SN1, E2, E1

HW - name alkyl halides - NaCN, CH3SNa, NaI - mesylate, triflate - leaving group ability - NaCN, DMF - Nai, acetone/heat - THF/heat - cyclization reactions - SN1 reactions - MeOH/ heat - Br2, hv/ SOCl2/ DMF, heat - t-BuO Na - K O-t-Bu/THF - NaOEt - H3C-C---C-Li; LiOH

CH 7: Alkenes NOTES - double bond, physical properties, nomenclature, stability - overlap of electron density - taxol - strained vs unstrained - hydrogenation - t-BuOk, NaOEt, Ko-t-Bu, THF, NaOEt, EtOH - Alkene synthesis - elimination, dehalogenation, dehydration of alcohols, catalytic cracking, dehydrogenation of alkanes, - reactions of alkenes - cis adddition, trans addition, ionic addition, addition of h2o, addition of H2so4, addition of Hg(Oac)2, addition of halogens, NaBH4 - addition of X2 and nu, radical addition of HBR, PhCO2-O2CPh, stepwise cis, addition of carbenes, epoxidation, m-CPBA, ZN(Cu) - addition of borane, addition of OsO4, addition of KMNO4, Ozonolysis, - meta-chloroperoxybenzoic acid (m-CPBA)

SCHEMATIC DIAGRAM

- Radical - Carbocation

- cis - trans

HW - isomer greatest dipole - naming - stable or unstable - K OtBu, THF, NaOEt, EtOH, NaO-t-Bu - H-SO4H/heat - H2SO4/heat; SOCI2/heat, acetone; KO-t-Bu/THF - H-Cl - Pt, 500oC - H-Br - H-A - Hg(OAc)-O(Ac) - Br-Br/CH2Cl2; (PhCO2)2, hn, HBr, LiOH, THF - Cl-Rh-PPh3-Ph3PPPh, Me3Si - Zn(Cu)/CH2I2; CHBr3/NaOH - H2/Pd-C, - SOCl2/acetone, Zn, CH2I2 - BH3, H2O2 - m-CPBA - OsO4 - O3/Me2S Transformation - NaOEt/THF; O3/Me2S - KMnO4/hot; NaOet/THF, - NBS/heat; NaOet; O3, CH2Cl2/Me2S - HCl/CH2Cl2; HBr/(PhCO2)2; H2SO4/H2O;

CH 8: Alkynes NOTES - Nomenclature - Bonding and properties - acetylide anions - BuLi, H3C-Li - synthesis of alkynes from dihalides NaNH2 - Addition reactions of alkynes - reaction with halogens; reactions HX, major, minor; reaction with HgSO4, HgSO4/H2SO4, H2O; O3SO-H - hydroboration of acetylenes (cis) - enolate - H2O2, NaOH - hydrogenation - Pd, H2, BaSO4 - Birch reduction - cleavage of alkynes - KMnO4, H2O, neutral; KMnO4/hot; HCl; O3, H2O

SCHEMATIC DIAGRAM - anti-markovnikov additions - formation - markovnikov addition - deprotonation - cis addition - trans addition - cleavage - multiple addition

HW - naming - LiCH3, TsO - NaNH2 - MeLi, CH3I - H-NH2 - Br2 (excess) - HBr, CH2Cl2 (1 equivalent) - MeLi/MeI; HBr/(PhCO2)2 heat; Me2CuLi/THF; - H2SO4/HgSO4/H2O - Sia2Bh/H2O2,NaOH - H2, Pd-C, quinoline - HBr/(PhCO2)2 heat - NaNH2 heat H2O - Sia2BH - H2O2 - O3; H2O - OsO4, H2O2 - Ph - HCO2H - HCO3H - Pd-C - H2 - MeLi, EtBr, PCC -LiAlH4 - D2O - NaC CMe...