Exam 3 Flashcards
Grignard (R-MgX) and 1.CO2, 2.H2O
Makes a carboxylic acid by first adding Mg to the existing R group on the molecule such as a phenyl ring with Br. Then Mg attacks C and creates carboxylic acid where Mg was.
Cuprates 1.(R2CuLi) 2. H2O
Adds only one R group except it adds it to the beta position which is the second carbon away from the carbonyl. This is only when there is a carbonyl and double bond. Prefers C=C. If there is no other double bond then changes carbonyl to OH and R group.
Grignards 1.(R-MgCl) 2.H2O
Grignards don’t care about alpha and beta. They only react with the carbonyl, changing it to an OH and an R group.
Hydrogenation 1.NaBH4 2.H2O
Changes carbonyl to OH and H. Not chemoselective
H2(1 equiv), Pd/C
Pd is chemoselective for C=C so ignores carbonyl and adds an H to each side of double bond
H2(excess), Pd/C
Causes a total reduction but C=C goes first. So adds one H to each side of double bond then changes carbonyl to OH and H.
Radical Halogenation (Br2, 🔺)
All Alkanes must start with this! Adds a Br
DBU or DBN or KotBu
Elimination. Turns Br into Double bond inside the ring
Hydration (H2SO4, H2O)
Changes Alkene into Alkane with OH
K2Cr4O7 or PCC or CrO3,H2SO4, H2O
Changes OH into carbonyl
1.CH3MgBr 2. H2O
Changes carbonyl into OH and CH3
Can make grignard from HOCH3 and PBr3. Then you get BrCH3 then you add Mg•
H2SO4, H2O or POCl3
Causes elimination of the OH but not the R group
ToSCl and pyridine
Changes OH to OTs
HBr, HCl or PBr3, SOCl2
Changes OH into X
PCC or Cr3O3, H2SO4, H2O
Or K2Cr4O7
Or Na2Cr4O7
Changes OH into carbonyl
H2SO4, H2O or POCl3
Eliminates OH changing alkane to alkene
- NaBH4 2. H2O or
- LiAlH4 2. H2O
with a aldehyde or ketone
Becomes primary alcohol (R connected to OH) if SM is aldehyde
Becomes secondary alcohol (Two Rs and an OH) if SM is a ketone
Organometallic (Li-CH3 or Li-R or Na-C triple bond C-R
Changes carbonyl to OH and whatever the “R” group is connected to the metal.
NaCN, HCN
Changes carbonyl into cyanohydrin. (OH group and CN) (keep existing groups from carbonyl always for everything)
H2O, H+(generic acid) or H2O,OH- (generic base)
reacting with a cyanohydrin (something with CN)
Adds a carboxylic acid to the C in the C triple bond N. N disappears
Wittig Reaction (Ph3P=R)
Gets rid of O on starting material, adds C instead and rest of R group attached to the Ph3P.
(Replaces carbonyl with its own double bond and junk) creates a biproduct of O=Ph3P
When doing retrosynthesis, want to put Ph3P on one with fewer R groups
Add O to one with most R group to make carbonyl and add PPh3 to other one
Primary amine and “mild acid”, or H+, H3O+, or HA
Primary amine has one C directly attached to it.
Causes a imine and (H2O) (two H goes into the H2O)
Imine is one that looks like a carbonyl just with an N instead of an O. N acts as glue for the two pieces.
Secondary amine and “mild acid”, or H+, or H3O+, or HA
N replaces O on carbonyl and act like glue to hold all the pieces together. Creates enamine, weird side alkene. (Bi product is still H2O) creates from H2 leaving N and O leaving carbonyl.)
Hydrolysis of imines.
Imine and H2O, H+
Turns imine into both original parts. Adds O to double bond where N was and takes off N and R group in a chunk then add H2 to N
