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22 notecards = 6 pages (4 cards per page)

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Organic Chemistry I Test #4 Reactions

front 1

KMnO4/NaOH, cold

or

OSO4 cat/NMO

back 1

Syn-Dihydroxylation -> Adds OH & OH CIS

front 2

1. Hg(OAc)2, H2O/ 2. NaBH4

back 2

Oxymercuration-Demercuration -> Adds H and OH, OH to MORE substituted position

front 3

1. BH3 * THF/ 2. H2O2, NaOH

back 3

Hydroboration-Oxidation -> Adds H and OH, OH LESS substituted position

front 4

HBr/ROOR

back 4

Hydrohalogenation -> Adds H and X, X to LESS substituted position

front 5

Br2/ CCl4

back 5

Halogenation -> Adds X & X, ANTI

front 6

H3O+

or

H2SO4 cat./H2O

back 6

Acid-Catalyzed Hydration -> Adds H & OH, OH on MORE substituted position, rearrangement is possible

front 7

HCl

back 7

Hydrohalogenation -> H & X, X in MORE substituted position, rearrangement is possible

front 8

Br2/H2O

back 8

Halohydrin Formation -> Adds X & OH, ANTI, OH in MORE substituted position

front 9

H2, Pt (Pd, Ni)

back 9

Catalytic Hydrogenation -> Adds H & H, CIS, (murder double bond)

front 10

1. RCO3H/ 2. H3O+

or

1. MCPBA / H3O+, H2O

back 10

Anti-Dihydroxylation -> Adds OH and OH, ANTI

front 11

1. O3/ 2. DMS

or

1. O3 / 2. Zn/H2O

back 11

Ozonolysis -> Cut double bond in half and add O's

front 12

Na (s) / NH3 (l)

back 12

Dissolving Metal Reduction of Alkynes -> TRANS ALKENE

front 13

H2 / Metal (Pt, Pd, Ni)

back 13

Reduction of Alkynes Catalytic Hydrogenation -> ALKANE (murders all PI bonds)

front 14

H2/ Lindlar's catalyst

back 14

Reduction of Alkynes Catalytic Hydrogenation -> CIS-ALKENE

front 15

1. O3 / 2. H2O

back 15

Ozonolysis of an Alkyne -> Internal: 2 Carboxylic acids

Terminal: Carboxylic acid + CO2

front 16

xs X2 / CCl4

back 16

Halogenation of Alkynes -> Adds 4 X's (tetrahalide), VINCINAL

front 17

X2 / CCl4 (1 eq)

back 17

Halogenation of Alkynes -> Adds 2 X's, ANTI

front 18

HX (1 eq)

back 18

Hydrohalogenation of Alkynes -> Adds H & X, X in MORE substituted position

front 19

xs HX

back 19

Hydrohalogenation of Alkynes -> Add's 2 X's & H, geminal dihalide, X's in MORE substituted position

front 20

1. NANH2 / 2. Alkane with leave in group

back 20

Alkylation of Terminal Alkynes -> Sticks alkane onto end of triple bond

front 21

NaNH2 / NH3

back 21

Preparation of Alkynes -> Internal Alkyne

front 22

1. xs NaNH2/NH3 / 2. H2O

back 22

Preparation of Alkynes -> Terminal Alkyne