36. Propose the mechanism for each of the following transformations: LOH oonc. HSO Heat (a) conc. H,SO Heat "ОН (Ь) cone. HS0 Heat (c)

EBK A SMALL SCALE APPROACH TO ORGANIC L
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Publisher:Lampman
Chapter20: Nucleophilic Substitution Reactions: Competing Nucleophiles
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36. Propose the mechanism for each of the following transformations:
OH
conc. H,SO4
Heat
(a)
conc. H2804
Heat
(b)
"OH
cone. HSO,
Heat
(c)
"OH
Transcribed Image Text:36. Propose the mechanism for each of the following transformations: OH conc. H,SO4 Heat (a) conc. H2804 Heat (b) "OH cone. HSO, Heat (c) "OH
Things to memorize and understand.
Weak / Weak
Nucleophile
(only)
Base
Strong/Strong
Nuc/ Base
(only)
Nuc
Base
Halides
Sulfur nucleophiles
(of NaH)
HO
H2O
HS
H,S
DBN
Meo
MEOH
Br
RS
RSH
DBU
ELOH
Eto
1°
E2
SN2
Minor
Major
Strong
Nuc
Strong
Base
2°
E2
SN2
Major
Minor
Examples: RO, HO
3°
E2
Not
1°
SN2
E2
practical
Weak
Weak
Base
Not
2
SN2
SN1
E2
E1
Nuc
practical
Examples: ROH, H2O
3°
SN1
E1
Transcribed Image Text:Things to memorize and understand. Weak / Weak Nucleophile (only) Base Strong/Strong Nuc/ Base (only) Nuc Base Halides Sulfur nucleophiles (of NaH) HO H2O HS H,S DBN Meo MEOH Br RS RSH DBU ELOH Eto 1° E2 SN2 Minor Major Strong Nuc Strong Base 2° E2 SN2 Major Minor Examples: RO, HO 3° E2 Not 1° SN2 E2 practical Weak Weak Base Not 2 SN2 SN1 E2 E1 Nuc practical Examples: ROH, H2O 3° SN1 E1
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