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- 4-chloro-3-methoxyheptane
- DO NOT get priority in numbering
- alphabetical order
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IUPAC: ether end with?
oxy
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symmetrical ether common naming
diethyl ether
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Prepraparation of alcohols:
synthesis undergoes what mechanism?
- SN2 only
- (no extra products)
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preparation of alcohols:
reaction involves:
______ + _____ ----> alcohol
alkyl halide + -OH ---> alcohol
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What kind of alkyl halides work for alcohol synthesis?
- methyl/1°: best, fastest, highest yield, less sterically hindered
- 2°: works but has competing E2 rxn
- 3°: DOES NOT WORK
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Preparation of ethers:
reaction involves:
______ + _____ ----> ethers
alkyl halides, -OR
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Preparation of ethers:
prefers what kinds of R-X?
- methyl/primary: favorite, best, high yield, less sterically hindered
- secondary: works okay
- tertiary: NEVER
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what is an epoxide?
cyclic ether
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Preparation of epoxides:
_______ + _____ ----> epoxide
halohydrin, NaH
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RXNs of alcohols:
dehydration with...
H2SO4 (sulfuric acid) and TsOH
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all dehydrations form..
alkenes
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alcohol synthesis only happens through what mechanism?
SN2 ONLY
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ether synthesis happens through what mechanism?
SN2 only
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H2SO4 (sulfuric acid) and TsOH rxn's with alcohols result in...
dehydration, alkenes
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True/false:
H2SO4 (sulfuric acid) and TsOH have the same effect
- true
- H2SO4 (sulfuric acid) = liquid
- and TsOH = solid
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Mechanism for H2SO4 (sulfuric acid) and TsOH on methyl/primary alcohol
E2, no E1 b/c primary carbocation is too unstable
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Mechanism for H2SO4 (sulfuric acid) and TsOH rxn on secondary and tertiary
E1 (carbocation intermediate)
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Secondary carbocations can do what for stabilization?
rearrange
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three ways to do dehydration
- H2SO4 (sulfuric acid)
- TsOH
- POCl3 + pyridine
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POCL3 + pyridine mechanism
E2 only, results in alkene
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How to convert alcohol into alkyl halide
R-OH --(H-X)--> R-X + H2O
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Mechanism for R-OH into R-X with methyl/primary
SN2
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Mechanism for R-OH into R-X with secondary/tertiary
SN1
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What does SOCl2 + pyridine do?
converts alcohols (R-OH) to R-Cl
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mechanism for SOCl2 + pyridine
- SN2 only
- NEVER ON TERTIARY
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What does PBr3 do?
converts R-OH into R-Br
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mechanism for PBr3
- SN2 only = inversion
- no rearrangements!
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ether + alkyl halide = ?
2 alkyl halides
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what mechanism does conversion of ethers into alkyl halides undergo?
can do SN1 and SN2, both, or double up on one (two steps)
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Ring opening of epoxides with strong nucleophile will...
attack, then protonate
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ring opening of epoxides with weak nucleophile will...
protonate, then attack
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strong acids will open epoxides from...
more substituted carbon
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nucleophiles will open epoxides from...
least hindered (substituted) carbon
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