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49 Cards in this Set
- Front
- Back
solvent for SN2 and BH3 and mercuration reactions
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THF
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to add 2 carbons and O (at the end of carbon chain)
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Epoxide
(with grignard, Li or MgBr) |
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to add 3 carbons and O (tetrahedral shaped)
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Carbonyl
(with grignard, Li or MgBr) |
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to brominate at a tertiary or secondary carbon
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Br2, hv
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to convert a carbonyl to an alcohol
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H2, Pd/C
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to convert a R-C=C-R into a double alcohol (one wedged, one dashed)
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MCPBA
(in CH2Cl2 solvent) (with H+/H2O) |
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to convert alcohol (with halogen anti-periplanar to OH group) to epoxide
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OH-
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to convert alcohol into carbonyl (C-OH → C=O)
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PCC (in CH2Cl2 solvent)
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to convert alcohol into carbonyl (C-OH → C=O)
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Na2Cr2O7 (with H2SO4)
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to convert alcohol into haloalkane
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R-OH → R-X
R Br Cl I 1,2 PBr3 SOCl2 PI2 3 HBr HCl HI |
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to deprotonate alcohol
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NaH or EtO-
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To convert alkene alcohol to carbonyl
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Tautomerization
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to convert alkene into alcohol with halogen (on opposite sides, one wedged one dash)
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Cl2 (with H2O)
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to convert alkene into carbonyl
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O3 (with Me2S)
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to convert alkene to alcohol (markovnikov)
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H+ (from acid)
(with H2O) |
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to convert alkene to alcohol
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Hg(O=OCCH3)2
(with H2O, NaBH4, NaOH (solvent), H2O workup) |
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to convert alkene to alcohol
to convert alkyne to alkene alcohol (ANTI MARKOVNIKOV, syn addition) |
BH3 (in THF solvent)
(with H2O2, OH-) |
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to convert alkene to alcohol (with halogen) (markovnikov)
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RCO3H (in CH2Cl2 solvent) (with X-, H2O)
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to convert alkene to alcohol (with halogen) (anti markovnikov)
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RCO3H (in CH2Cl2 solvent)
(with HX) |
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to convert alkene to alkane
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H2, Pt
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to convert alkene to an epoxide
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MCPBA
(in CH2Cl2 solvent) |
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to convert alkene to anti double alcohol
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MCPBA --> H2O
RCO3H (in CH2Cl2 solvent) (with H+, H2O, or OH-) |
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to convert alkene to double haloalkane (adds on opposite side (one wedge, one anti)
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Cl2 (with CCl4)
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to convert alkene to halalkane (Markovnikov)
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concentrated HX
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to convert alkene to syn double alcohol
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kMnO4 (with H2O)
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to convert alkene to syn double alcohol
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OsO4 (with H2S)
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to convert alkyne to trans alkene
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Na (with NH3)
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to convert alkyne to cis alkene
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H2, Lindlar
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to convert alkyne to alkene halogen
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concentrated HX (X on non terminal)
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to convert alkyne to double halogenated alkene (cis)
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Br2
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to convert alkyne to longer alkyne alcohol
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RLi (in THF solvent)
(with epoxide and H2O) |
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to convert carbonyl to alcohol
(reduction) |
LiAlH4
(with aprotic solvent [ether] and H2O) |
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to convert carbonyl to alcohol (reduction)
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NaBH4
(with EtOH solvent) |
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To convert double haloalkane to alkyne
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Na (with NH3)
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to convert epoxide to alcohol
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concentrated HX (attaches to MOST hindered base of epoxide)
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to convert epoxide to alcohol
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nucleophile (attaches to least hindered base of epoxide)
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to convert haloalkane to alkene
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strong base or reagent (e1, e2, etc.)
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to convert haloalkane to thiol
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SH-
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to convert tertiary alcohol to alkene
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concentrated H2SO4
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to make a haloalkane form an alcohol
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primary: pbr3, socl2, pi2
secondary: pbr3, socl2, pi2 tertiary: hbr, hcl, hi |
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to convert alkene to oxacyclopropane
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CH2I2/Cu
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to attach Br one single bond away from an alkene double bond
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NBS
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1050-1100
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C-O
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2700-2900
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O-C-H
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915-995
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terminal alkene
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2900
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C-H (sp3 hybridized)
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2100-2260
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C---C (alkyne)
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1680-1640
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alkene (C=C)
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3020-3100
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=C-H
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