Alcohol Just Reagengs Flashcards
(32 cards)
An alkanol reacts with PBr3 what stereochem ?
Br replaces OH and inverts stereochem
An alkanol reacts with SOCl2 and Pyridine
Cl replaces OH and inverts stereochem
Without base ur retains stereochem
Alkanol reacts with HCl and ZnCl2
Replace OH with cl
Alkanol reacts either DMP and CH2Cl2 which is the same as SWERN and PCC
OH turns into a H group and a double bond oxygen is on the site of attack essentially forming an ALDEHYDE
Alkanol 1degree reacts with NaCr2O7 and an acid
Carboxcylic acid is formed so the OH group remains unchanged and a double bond with an oxygen is on the attack site
Alkanol 2 degree reacts with NaCr2O7 and an acid
Ketone is formed so the OH turns into a O double bonded to the C
Alkanol reacts with elemental metal like Li or Na
The alcohol is deprotenated and forms a alkoxcide which is a negatively charged O
AlkanOL reacted with NaH a strong base
The alcohol is deprotenated and yields an alkoxide
AlkanOL reacts with TsCl and pyridine what is stereochem . Note this is the same as TFCl and TEA
The alcohol turns into a OTs group and retains stereochem
AlkanOL reacts with tert- butoxide
The alcohol is deprotenated and forms an alkoxide
If you wanted to extend an terminal alkanol chain how would you do it
1) SWERN to make an aldehyde
2) 1)organomegallic 2) H3O+ which brings us back to OH
In simple terms what does Jones, PPC, and SWERN DO in ONE step
It changes an alcohol to a ketone, aldehyde, or carboxcylic acid
In simple terms what does organometallics do in 2 STEPS
It turns a double bond to an O back to an OH and extends the chain from that point via organometallic and acid
What happens when we react a aldehyde with A hydride and list examples of hydrides
The aldehyde turns into a OH with NO addition of carbons to the chain
1) LiAlH4
2) H3O
Or NaBH4 and MeOH
How do we turn in aldehyde into an alcohol without extending the chain
Use a HYDRIDE
What are the Jones reagents
Na2Cr2O7 and Acid
Or
CrO3 and Acid
What are the Hydride reagents
1) LiAlH4
2) H3O+
How do I extend a ketone from an alkene
Use hydrogenation oxidation for addition of a terminal OH
Use swern to make an aldehyde
Use organo metalics to extend chain as desired and turn the O back to a OH
What happens when an alkonol reacts with a strong acid
Dehydration and formation of an alkene. WATCH FOR REARRANGEMENTS
What happens when OH reacts with H2CrO4
This is a jones so all OH of 1 and 2 degrees get oxidized to ketones or carboxcylic acids
What does NaNH2 acts as and do
A strong base that performs most substituted alkene
What does KmnO4 and a strong acid do to an alcohol
Turns it into a carboxcylic acid
What happens when a 1 degree halide reacts with NaOH
The Br is replaced with an OH
What is an sn1 regents to replace a halide with an OH
H2O