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Reactions of hexanol
from CH10, 5 reactions of hexanol.
23
Organic Chemistry
Undergraduate 1
09/13/2010

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Term
Cyclohexanol + (TsCl & Pyridine)
Step 2 : NaCN DMSO
Definition
Overall, CN replaces the OH
Term
Cyclohexanol + (SO2Cl2 & Pyridine)
Definition
Replace OH with Cl
Term
Cyclohexanol + H2SO4 and heat
Definition
a double bond in the ring
Term
Cyclohexanol + POCl3 & Pyridine (cold)
Definition
double bond in the ring
Term
Cyclohexanol + PBr3 & Pyridine
Definition
OH replaced by Br
Term
Cyclohexanol + Na2Cr2O7 or PCC
Definition
the OH becomes a double-bonded oxygen
Term
1-methyl-1-Cyclohexanol + HBR
Definition
Replace OH with Br
Term
1-methyl-1-Cyclohexanol + POCl3 & Pyridine (cold)
Definition
OH and methyl join together into a C=C off the ring.
Term
Cyclohexanol with a methene + BH3 THF H2O2 OH-
Definition
Methene becomes a methanol
Term
Cyclohexanol with a methanol + PCC
Definition
the O becomes double-bonded to the methane.
Term
Cyclohexanol with a methanol + Na2Cr2O7
Definition
another O is added, double-bonded to the methane. OH remains.
Term
acetylene + H2/Lindlars
step 2 : HBr
Definition
EtBr
Term
Cyclohexanol with a methanol + NaNH2
Step 2: EtBr + DMSO
Definition
OH becomes O-, which then has an ethane added to it.
Term
Acetylene + NaNH2
Definition
removes a Hydrogen, leaving it open to bond with anything.
Term
Acetylene + Na + NH3
Definition
takes the triple bond to a double bond
Term
1-methyl-Cyclohexane + Br/hv
Step 2: NaOtBu / HOtBu
Definition
First, a Br sticks off where the methyl is, then the Br and methyl are replaced by a methene.
Term
1-bromo-methyl-Cyclohexane + DMSO and a deprotenated acetylene
Definition
The alkyne bond replaces the Bromine
Term
Cyclohexane with a methyl and alkyne sticking off + HgH2SO4
Definition
Becomes an alkane structure with an oxygen double-bonded to the 2nd carbon.
Term
alkene bond + HgOAc + H20
Step 2: NaBH4
Definition
OH added to most subbed side
Term
Epoxide ring opening in basic conditions, where does the Nu go?
Definition
Least subbed side
Term
Epoxide ring opening in acidic conditions, Nu goes to....
Definition
most subbed side
Term
Epoxide + NaCN & DMSO
Step 2: H3O+
Definition
OH on most subbed, CN on least subbed
Term
to make an epoxide from a double bond use the reagent
Definition
mCPBA
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