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38 Cards in this Set
- Front
- Back
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Reduction |
Increasing hydrogen or decreasing oxygen content |
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Oxidation |
Increasing oxygen or decreasing hydrogen content |
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Alcohols by reduction of carbonyls |
Carboxylic acid(O=C-OH) to primary alcohol Aldehyde (O=C-H) to primary alcohol Ketone (O=C) to secondary alcohol Ester(O=C-O) to primary alcohol |
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Reduced by LiAH |
All carbonyl groups, carboxylic acids, ketone, ester, aldehyde |
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Reduced by sodium borohydride (NaBH4) |
Ketone and aldehyde |
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Swern oxidation |
Oxidation of primary alcohol to aldehyde or secondary alcohol to ketone DMSO, (COCl)2, Et2N COLD |
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Oxidation of primary alcohol to carboxylic acid |
Potassium permanganate (KMnO4), usually carried out in aqueous MnO2 |
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Oxidation of secondary alcohol to ketones |
Chromic acid, H2CrO4 and Jones reagent CrO3 |
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CrO3-> Cr3+ |
From 6+ to 3+, clear orange to greenish opaque |
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Prep of organolithium and organomagnesium |
Prepared by reacting alkyl halides with lithium or reactive halides in ether |
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Reactions of Grignard Reagents with Oxiranes (epoxides) |
Reaction results in a ring opening and formation of alcohol, occurs at the least substituted ring carbon, carbon carbon bond two bonds from the alcohol |
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Alcohols from Grignard reagents |
Aldehydes and ketones react to yield alcohols, esters=tertiary, ketone=tertiary, |
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Use of Lithium Reagents |
Organolithium reacts like a Grignard reagent Sodium alkynided react with aldehydes and ketones to form new C-C bonds |
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Reducing agents |
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Oxidizing agents |
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Toluene |
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Phenol |
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Aniline |
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Benzenesulfonic acid |
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Benzoic acid |
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Acetophenone |
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Anisole |
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Xylene |
Dimethyl substituted benzene |
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Huckel's Rule |
4n+2pi 2,6,10,16,18,22,etc |
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Pyridine |
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Pyrrole |
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Furan |
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Thiophene |
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Halogenation |
X2, FeX2 where X is Cl, Br Adds on X to benzene,HX is an additional product |
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Nitration |
HONO2, H2SO4 Adds NO2 to benzene, water is an additional product |
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Sulfonation |
SO3,H2SO4 Adds SO3H to benzene |
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Friedel-Crafts Alkylation |
RCl, AlCl3 (R can rearrange) Adds R group to benzene, HCl is additional product |
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Friedel Crafts Acylation |
RC(=O above)Cl, AlCl3 Adds O=C-R to benzene with HCl as additional product |
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Clemmensen reduction |
Reduces phenyl ketones to the methylene(CH2)group Zn(Hg), HCl in reflux or heat |
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Classification of substitutents |
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Birch Reduction |
Takes one double bond out of benzene Na, NH3, EtOH Li, liq. NH3, EtOh can be reduced further with H3O+, H2O |
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Directions |
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Anthracene, aromatic |
