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