Exam 1 - Ethers and Silyl Ethers Flashcards
If an unsymmetrical ether is treated with a strong acid (i.e. HI, HBr, HCl), choose the LG which produces a ___ ___ ___.
more stable carbocation
A ___ ___ alcohol treated with H2SO4 and heat will produce an ether product via SN2.
primary unbranched alcohol
Treating an alkene with ___ and ___ will produce a simple ether.
H2SO4, CH3OH
In Acid Catalyzed Addition of alcohols to alkenes to create ethers (H2SO4 and CH3OH), the alcohol adds to the side with the ___ ___ ___.
more stable carbocation
Silyl Ethers are the protecting groups for ___.
-OH
-OTMS, -OTBDMS, all Silyl Ethers are removed with ___ in the last step.
TBAF
In Acid Catalyzed Dehydration of alcohols (H2SO4 and heat), it only works with ___ ___ and can only make ___ ___.
primary alcohols, symmetric ethers
A ___ ether treated with a strong acid (i.e. HI, HBr, HCl) will go through SN2.
primary
An alkene reacting with H2SO4 needs ___ or a ___ ___ in order to do the reaction (produce an ether).
CH3OH, primary alcohol
Williamson Ether Synthesis with a ___ or ___ alkyl group will instead produce an alkene via elimination.
secondary, tertiary
___ ___ - Unreactive group that is reversibly created to prevent a functional group (like OH) from reacting and producing unwanted products.
Protecting groups
Acid catalyzed dehydration of alcohols only works for creating ___ ___ from ___ ___ alcohols.
symmetrical ethers from primary unbranched alcohols
A ___ or ___ alcohol treated with H2SO4 and heat will simply produce an alkene via EI.
secondary, tertiary
One can also make ethers via acid catalyzed dehydration. In this rxn, you use ___ with ___.
H2SO4 with heat
When treating an alkene with H2SO4 and CH3OH, a ___ is formed. The alcohol then adds to the ___ stable carbocation.
carbocation, more stable
In ___ ___ ___, one can treat a primary, secondary, or tertiary alcohol with a strong base (i.e. NaH) to produce an ether.
Williamson Ether Synthesis
Treating an alkene with H2SO4 and CH3OH will produce a simple ___.
ether
In Williamson Ether Synthesis, one can treat a primary, secondary, or tertiary alcohol with a ___ ___ and ___ ___ to produce an ether.
strong base (i.e. NaH) and alkyl halide
In Williamson Ether Synthesis, you will first make the ___, THEN the ether.
alkoxide
A primary unbranched alcohol treated with H2SO4 and heat will produce a(n) ___ product via ___.
ether via SN2
A secondary and tertiary ether treated with a strong acid (i.e. HI, HBr, HCl) will go through ___.
SN1
A ___ and ___ ether treated with a strong acid (i.e. HI, HBr, HCl) will go through SN1.
secondary and tertiary
Once TBDMSCl is added to the -OH, write it as:
-OTBDMS
Williamson Ether Synthesis only works with ___ or a ___ ___.
CH3, primary LG
___ ___ are the protecting groups for -OH.
Silyl Ethers
A primary unbranched alcohol treated with ___ and ___ will produce an ether product via SN2.
H2SO4 and heat
An ether can be treated with a ___ ___ to split it apart and create an alcohol and an alkyl halide.
strong acid (i.e. HI, HBr, HCl)
A secondary or tertiary alcohol treated with H2SO4 and heat will simply produce a(n) ___ via ___.
alkene, EI
In Williamson Ether Synthesis (strong base+ alkyl halide), the alkyl halide must be ___ or ___.
methyl or primary
A primary ether treated with a strong acid (i.e. HI, HBr, HCl) will go through ___.
SN2
In Williamson Ether Synthesis, one can treat a ___, ___, or ___ alcohol with a strong base (i.e. NaH) and alkyl halide to produce an ether.
primary, secondary, tertiary
A secondary or tertiary alcohol treated with ___ and ___ will simply produce an alkene via E1.
H2SO4 and heat
Best Silyl Protecting Groups to add to protect/hide -OH groups:
TMSCl, TBDMSCl
Williamson Ether Synthesis with a secondary or tertiary alkyl group will instead produce a(n) ___ via ___.
alkene, elimination
Once TMSCl is added to the -OH, write it as:
-OTMS
