University:
Eastern Kentucky University
Course:
CHE 361 | Organic Chemistry I
Academic year:

2023
Views:

305

Pages:

3
Author:

Charlee Buchanan

Functional Groups IUPAC Name O Amine Ether H-C-OH N-H₂ O-R Aldehyde R-NH₂ R-O-R O=C-OH Alcohol O-C-OH Carboxylic Acid R-OH Amide Identify Longest C-chain Root Name Substituents have lowest numbers 4-ethyl-5,6-dimethylnonane meth = 1, eth = 2, prop = 3, but = 4, pent = 5, hex = 6, hept = 7, oct = 8, non = 9, dec = 10 Carbocations Stability 3° > 2° > 1° positive charge = C-sp² empty p-orbital = low electron density 3° carbon w/ 2° = 72° positive charge CH₃ attached Resonance Stabilized Hybridization CH₄ H groups = Sp³ C-C-H - groups -> Sp³ H-C≡C-H 2 groups -> Sp 3 groups -> Sp² Formal Charge VC - (B + L) valence electrons - (bonds + lone pairs) Lewis Structure Cyanide ion (C≡N) - must have a full octet and formal charge - minimal FC Resonance Structure If π e- pair atom is moving from one spot to another, it is not a RS. Only electron is free to move No. of e- stay the same Lewis Base nucleophile: electron rich can donate electrons H₂O - water HO- - hydroxide CH₃O- - methoxide need lone pair to donate H₂O acts as Lewis base Acids pKₐ ↓ strength ↑ CH₃COOH CH₂COOH CF₃COOH CCl₃COOH CH₃COOH pKₐ = 4.8 CH₃COOH pH = 4.8 If you don't know the pKₐ of an acid that's connected to OH IUPAC Name Configuration Rank each group based on atomic no. and if there is a tie, look at where it's connected. If the lowest priority is H- in the back (R) If S Counterclockwise R Clockwise S If D (H-) is in front Flip the answer Enantiomers no plane of symmetry, non-superimposable mirror images. must have at least one stereocenter. ex: CH₂BrCl, CHBrCl₂ Conformation trans - 1-bromo-4-methylcyclohexane trans - functional groups at opposite positions cis - functional groups at same position SN2 Reaction bulky methyl groups block SN2 methyl > 1° > 2° > 3° vinylic halide will not work inversion of configuration Free Radical Termination A• + B• → A-B A• + A• → A-A A-A → Initiation IUPAC Name Identify longest chain Find configuration Name substituents If there is a tie, look at where it's connected ex: (2R, 3R)-2-bromo-3-chloropentane Major Products PBr₃ converts to primary and secondary alcohols to alkyl bromides Newman Projections (CH₃)₂CHCH(CH₃)CH₂CH₃ (CH₃)₂CH CH₂CH₃ CH₃ CH₃ CH₃ Radical A 3° allylic radical allylic/benzylic 3° > 2° > 1° allylic benzylic Racemic mixture Chiral products Approach from above and below Reagent -SN1 Reaction* H₂SO₄ H₂O H₂O, H₂SO₄, Heat Hg(OAc)₂, H₂O, NaBH₄ BH₃ • THF, H₂O₂ NaOH MCPBA CH₂Cl₂ KMnO₄, H₂O, cold KMnO₄, H₂O, heat OsO₄, H₂O₂ mCPBA Major Product [R] 2-bromo-3-methylcyclohexane products with NaI in Acetone* [S] 2-bromo-3-methylcyclohexane* (CH₃)₂CHCH₂OH with HBr* CH₃CH₂CH(Br)CH₃ with NaBH₄, H₂O* H₂O, NaOH, H₂O₂* (CH₃)₂CHCH₂OH with HBr in dark* Propene with Bromine in H₂O MESO H₂O, NBS, heat or light, or hv vinylic not stable Reagent CH₂Cl₂, -78°C Pka CN > OH > NH protic amine > amine alkane, alkene, alkyne acidic low pKa = strong acid