TOSYLATION OF ALCOHOLS
WHAT TYPE OF PATHWAY?
SN2
NAME THE STRONG OXIDIZERS USED (AT LEAST 3)
KMNO4, CrO3, Na2Cr2O7, (ANY CHROMIC BASED OXIDIZERS CAN BE USED)
FISCHER ESTERIFICATION TURNS AN ____ INTO AN ESTER.
ALCOHOL
WHAT IS STEP 1? WHAT REAGENTS ARE USED?
HALOGENATION
PBr3, SOCl2
CAN YOU USE SECONDARY ALCOHOLS FOR THIS REACTION?
NO, ONLY PRIMARY
WHAT TYPE OF ALCOHOLS ARE ABLE TO UNDERGO TOSYLATION?
PRIMARY AND SECONDARY
STRONG OXIDIZERS WILL TURN PRIMARY ALCOHOLS INTO WHAT CARBONYL GROUP?
CARBOXYLIC ACID
WHAT REAGENT IS USED WHEN COMBINING THE CARBOXYLIC ACID WITH AN ALCOHOL TO CREATE AN ESTER?
STANDARD ACID
WHAT IS STEP 2?
ADD AN ALCOHOL TO THE PRODUCT FROM STEP 1
WHAT TYPE OF ETHER DOES THIS REACTION PRODUCE?
SYMMETRICAL ETHERS
WHAT HAPPENS IF YOU ADD A STRONG BASE TO OTOS OR AN ALKYL HALIDE?
IT WILL BE SUBSTITUTED (SN2)
STRONG OXIDIZERS WILL TURN SECONDARY ALCOHOLS INTO WHAT CARBONYL GROUP?
KETONE
WHAT DO YOU REMOVE FROM THE CARBOXYLIC ACID?
OH
WHAT PATHWAY? IS THERE A CARBOCATION INTERMEDIATE?
SN2-LIKE
NO CARBOCATION
WHAT REAGENT IS USED?
STANDARD ACIDS
IF YOU ADD AN ALCOHOL TO A TOSYLCL/PYRIDINE, WHAT IS THE SIDE PRODUCT?
HCL
HOW DO YOU TURN A PRIMARY ALCOHOL INTO AN ALDEHYDE? CAN YOU OXIDIZE TERTIARY ALCOHOLS?
VIA SPECIALIZED OXIDIZERS
YOU CANNOT OXIDIZE TERTIARY ALCOHOLS
WHAT DO YOU REMOVE FROM THE ALCOHOL?
H
DRAW THE FINAL PRODUCT USING SOCL2 DURING STEP 1.
CARBOXYLIC ACID CONNECTED TO THE ALCOHOL, (CONNECTED WITH AN OXYGEN)
DRAW THE MECHANISM FOR THIS REACTION.
O FROM THE ALCOHOL ATTACKS THE H FROM THE REAGENT (ACID OR WATER)
PROTONATED FORM IS ATTACKED BY THE NON PROTONATED FORM, RELEASING A WATER
WATER ATTACKS THE H WHICH KICKS OFF THE +
DRAW THE STRUCTURE OF A TOSYLCHLORIDE (TOSYLCL)
CENTRAL S, BONDED TO A CL, 2 OXYGENS (DOUBLE BONDS) AND A BENZENE RING WITH A METHYL ON THE BENZENE RING.
NAME THE SPECIALIZED OXIDIZERS (3)
Cu(S), PCC, DESS MARTIN PERODINANE
WHAT IS THE SIDE PRODUCT OF THIS REACTION?
WATER
DRAW THE FINAL PRODUCT USING PBr3 DURING STEP 1.
CARBOXYLIC ACID CONNECTED TO THE ALCOHOL, (CONNECTED WITH AN OXYGEN)
WHY DO WE NOT COMMONLY DO MIXED REACTIONS?
THEY YIELD TOO MANY ETHER COMBINATIONS