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Lecture

CHEM212 Formulas.pdf


Department
Chemistry
Course Code
CHEM 212
Professor
Mike Daoust

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CHEM 30A/30B
(Yves Rubin)
Alkane Formation: Corey-Posner reaction. (THIS IS NOT COVERED IN F&B!)
H
R–X
D
1) Li
2) CuI R2CuLi R–R'
Br
Overview of most Reactions Emphasized in 30A / 30B
CH2Br
dialkyl cuprate
R'–X
only primary alkyl,
secondary cyclic,
or phenyl halide
any alkyl or
cycloalkyl halide
with X = Cl, Br, I
CX
Deprotonation/Protonation:
H
R'
R
R–H B or B: RA-H
(or A-D; A-T)
CNu
any base stronger
than R
H
R'
R
any acid stronger
than R–H where H+,
D+, or T+ is transferred
1) NaNH2
2) D2O
Typical Example:
R–H (or R-D; R-T)
1) Li
2) CuI
Typical Example:
n-Bu2CuLi
Nucleophilic Substitution: SN2
Nu or Nu:
H3CBr
any non-tertiary
alkyl halide;
X = good leaving group
any good nucleophile;
best in polar,
aprotic solvent
inversion of configuration
at asymetric carbon
H3CCN
Typical Example:
K+CN
DMF
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