Chapter 14 Ethers.... Flashcards
(24 cards)
Ethers have low boiling points due to a lacking of what intermolecular force
Hydrogen bonding
Ethers have low reactivity making them good what?
Solvents
Best at solvating what type of ion,
Cations
Crown ethers are used to do what
Encapsulate cations
Epoxides are
Three member ether rigs
Four member ether rings
Oxetanes
Five member ether rings are
Furanes
Six member ether rings
Pyrane
Williamson ether synthesis requires
Alkoxide and alkyl haylide
Can phenols be used as alkoxide or alkyl halide in Williamson ether synth.
Alkoxides
Why can’t phenols be used as alkyle halides in Williamson ether synth.
Hindrance from the ring structure doesn’t allow an SN2 attack by the alkoxide
Alkoxy murcuration requires what to create an ether
Hg(OAc)2 …mercury TWO acetate
An alcohol ….. ( NOT H2O )
Is Demucuration the same in ether synthesis as it is in alcohol synth?
What is needed
Yes.
Na BH4…. Sodium borohydride
Ethers will react with strong hydrohalic acids in XS to give
Two alkyl halides
In the cleavage of an ether with strong hydrohalic acids undergoes what reaction types
One SN2
One dehydration SN1
Diphenyl ethers will not undergo what reaction with strong acids
Cleavage
What is a protection group
Lone functional group used to protect a functional group from reactions
Deprotection is used when
When the reaction is concluded or when the Protected needs modification
Epoxidation synthesis reacts what two reactants
An alkene
MCPBA or proxy acid.
Epoxides are hydrated to yield
Anti di-ols
Epoxides can react with acid and H2O to create diols. What is the other way to use Epoxides to make diols
1) . Use a hydroxide to attack the least substituted carbon on the Epoxides.
2) protonate the hydroxide
What type of reactions create Epoxides
Base promoted cyclist ion of halogens
Epoxidation of alkenes with. MCPBA or peroxy acid
Base promoted cyclization reacts a strong base with what to produce an Epoxides
Anti configured alcohalide
Gringards always attack what carbon on an Epoxides
Least substituted