University:
Massachusetts Institute of Technology
Course:
5.12 | Organic Chemistry I
Academic year:

2024
Views:

353

Pages:

5
Author:

Bennett Faulkner

5.12 Review Session: Exam I Key I. Review of Lewis Bonding Theory CH₂N₂ CH₂=N=N: H-C-H | H-C-N=N: | H (CH₃), CCHCH₂ (CH₃), C(OH)CH₂CH(CH₃)₂ H₃C-C-O: + H₂C=C=O → H₃C-O-CH₂ + H₃C-O-CH₂ II. Resonance O is more E.N. than C. Slightly less stable because charges are further apart (charge separation) III. Review MO Theory IV. Hybridization / LCAO b) The π-overlap in a) is geometry-dependent. Look at the Newman projection NO OVERLAP You have to break the π-bond to rotate this molecule! IV. Properties of Molecules CH₃N: yes, N has an extra lone pair BF₃: no, BF₃ has only 6 e-, no lone pairs H₂O: yes, O has two lone pairs CH₄: no, C has no lone pairs Bromated: CH₃-CH₂-Br + CH₃-CH₂-OH → CH₃-CH₂-O-CH₃ + HBr Lewis: CH₃-CH₂-Br + :Ö-CH₃ → CH₃-CH₂-O-CH₃ + Br⁻ a) HO-H H₂N-H HS-H atom size ↑, electronegativity ↓ b) F₃C-OH H₃C-OH H₃C-OH resonance, inductive effects c) H₃C-CH₂ H₂C=CH₂ H₂C≡CH hybridization III. Alkanes Problem 3 will not be covered on the exam n-pentane 2-methylbutane 2,2-dimethylpropane C₇H₁₂ d.o.u. = 2