Chapter 7-9 Reagents Flashcards
Strong Base / Weak Nucleophile
DBN, DBU, NaH
Strong Base / Strong Nucleophile
NaOH, NaMeO, NaEtO, (T-buok)
Weak Base / Strong Nucleophile
I, Br, Cl, Hs, Rs, RSH, H2S
Weak Base / Weak Nucleophile
H2O, EtOH, MeOH
HBr—>
double bond.
Adds Br on the most substituted carbon.
Addition.
Br2–>
double bond.
Adds a 2 Br molecules. One will be wedge one will be dashed.
Adds across the double bond
Br2,H2O
double bond.
Br molecule added on the least substituted carbon.
OH added on the most substituted carbon.
Will produce an En
Double bond.
BH3•THF
—————->
H2O2NaOH
Adds a OH molecule on the least substituted carbon.
Produces an En.
Watch for creation of chiral centers.
H3O+
Double bond
Adds a OH molecule on the most substituted carbon.
KMNO4
——————>
NaOH + Cold
Double bond.
Two OH molecules added SYN across double bond.
Will produce an En
OSO4
——————>
NaHsO3,H20
Double bond
Two OH moles added SYN across the double bond.
O3
———>
DMSO
Double bond
Break at double bonds.
Pt
———->
H2
Double bond
Removes double bonds.
Hg(OAc)2,H2O
———————>
NaBH4
Double bond
Adds OH molecule on the most substituted carbon
RCO3H
———->
H3O+
Two OH molecules added across the double bond. In Anti formation. One dash. The other Wedge
Produces an En
xs Br
——->
Terminal Triple bond.
Alkyne to Alkane. Adds two molecules of Br to the most substituted carbon.
1.) xs NaNH2
—————>
2.) H2O
Terminal triple bond.
Eliminates Molecules bonded to carbons.
Turns alkanes to Alkynes.
H2
——->
Lindlars Cat
R- triple -R
Turns an alkyne to a Alkene with a CIS conformation.
H2
——>
Pt
R-triple-R
Removes all triple bonds.
Turns it into Trans conformation.
1.) O3
——>
2.) H2O
Terminal triple bond.
Adds double bonded O to the most substituted carbon. Also adds a carbon with two double bonded O’s
xs Cl2 [one Eq]
———->
CCl4
Terminal triple bond.
Turns a Alkyne to a Alkene adds a Cl to the least and most substituted carbons
xs Cl2 [Two Eq]
———->
CCl4
Terminal triple bond
Turns a Alkyne to a Alkane and adds two CL molecules on the most substituted carbon and the least substituted carbon.
1.) R2BH
———->
2.) H2O2NaOH
Terminal triple bond
Add an Double bonded O to the least substituted carbon and the add a H bond off of that.
ALDEHYDE.
HgSO4
————>
H2SO4, H2O
Terminal triple bond.
Add a double bonded O to the most substituted carbon.
KETONE
1.) NaNH2
————>
2.) MeI or EtI or a bond structure.
Terminal triple bond.
Use this to add carbon bonds on a Alkyne.
Na
——>
NH3 (l)
R-triple-R
Turns an Alkyne to an Alkene with a Trans connectivity
