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CHEM 210 Final Exam Reactions, 2024.

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CHEM 210 Final Exam Reactions, 2024. P450 [O] Breaks a double bond (even phenyl) to have add an oxygen that is bonded to each carbon of a double bond Rh/ Pt Dehydrogenation to form a double bond Br2 FeBr3 (cat) Adds a Br in the place of a hydrogen BH2-H Breaks triple OR double bond and adds H or BH2 to those carbons H2 NaNH3 Trans partial reduction of triple to double bonds H2 Lindrar's catalyst Cis partial reduction of triple to double bonds H2, Pd/C or PtO2 Full hydrogenation of all double and triple bonds to a single bond syn addition (1)O3 (2) Reductive workup (Zn, C2S, PPh3) Breaks double bond and puts oxygen at either end but leaves H Phenyl groups not cleaved (1)O3 (2) Oxidative workup (H2O2) Breaks double bond and puts oxygens at either end + transforms H into OH Phenyl groups not cleaved m-CPBA alkene to epoxide Adds an oxygen that is bonded to each carbon of a double bond OsO4 NaHSO3 workup Breaks double bonds and adds OHs KC4H9O Good Base for E2 Tosylate (TsO-) Triflate (TfO-) Mesylate (MsO-) OsO4 NaHSO3 workup Breaks double bonds and adds OHs KHnO4 +NaOH H2O Syn addition of 2 OH groups

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CHEM 210 Final Exam Reactions, 2024.
P450
[O]
Breaks a double bond (even phenyl) to have add an oxygen that is bonded to each
carbon of a double bond
Rh/ Pt
Dehydrogenation to form a double bond
Br2
FeBr3 (cat)
Adds a Br in the place of a hydrogen
BH2-H
Breaks triple OR double bond and adds H or BH2 to those carbons
H2
NaNH3
Trans partial reduction of triple to double bonds
H2
Lindrar's catalyst
Cis partial reduction of triple to double bonds
H2, Pd/C or PtO2
Full hydrogenation of all double and triple bonds to a single bond
syn addition
(1)O3
(2) Reductive workup (Zn, C2S, PPh3)
Breaks double bond and puts oxygen at either end but leaves H
Phenyl groups not cleaved
(1)O3
(2) Oxidative workup (H2O2)
Breaks double bond and puts oxygens at either end + transforms H into OH
Phenyl groups not cleaved
m-CPBA
alkene to epoxide
Adds an oxygen that is bonded to each carbon of a double bond




OsO4
NaHSO3 workup
Breaks double bonds and adds OHs
KC4H9O
Good Base for E2

, Tosylate (TsO-)




Triflate (TfO-)




Mesylate (MsO-)




OsO4
NaHSO3 workup
Breaks double bonds and adds OHs
KHnO4 +NaOH
H2O
Syn addition of 2 OH groups
Lewis Acid
accepts a pair of nonbonding electrons
Lewis Base
Source of nbe pair
carbocation
Open shell carbon w positive charge
carboanion
Negatively charged carbon
hydrogen bond donor
strongly electronegative atom such as N, O, or F
hydrogen bond acceptor
electronegative atom with long electron pairs
Bronsted Acid
Molecule that provides H+
Bronsted Base
Molecule with a lone pair of nbe that accepts H+

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