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55 Cards in this Set
- Front
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ROH+ HX yields
|
RX + H20
(Alkyl Halide from Alcohol and Hydrogen Halide) |
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ROH + SOCl2/PBr3
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RCl/RBr (for 1*, 2* Alcohols)
|
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R3CH + Cl2
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R3CCl
reagents: Cl2, light |
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ROH + Acid yields
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Alkene
reagents: acid catalyzed (H2SO4, H3PO4,) |
|
RX + Base yields
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Alkene
reagents: weak base (H3C2O-) |
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Alkene + H2/Pd
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Alkane
|
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Alkene + HX
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RX (Alkane)
|
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Alkene + HBr
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RX (Alkane)
reagents: ROOR anti-Markovnikov |
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Alkene + Acid
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RX
|
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Oxymercuration of Alkene
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Yields Alcohol
Reagents: Hg(OAc)2, H20, NaBH4 |
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Hydroboration-Oxidation of Alkene
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Yields Alcohol
Reagents: BH3, THF Then H2O2, NaOH, H20 anti-Markovnikov syn addition |
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X2 to Alkene
|
yields vicinal dihalide alkane
anti-Markovnikov anti addition |
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Prepare Vicinal Halohydrin from Alkene
|
yields vicinal halohydrin
reagents: X2, H20 OR NBS, DMSO, H20 X adds anti-Markovnikov anti addition |
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Epoxidation of Alkene
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yields epoxy
reagents: H3CCO2OH |
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Ozonolysis
|
cleaves alkene bonds with C=O bonds.
|
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Alkylation of Acetylene
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yields longer alkynes
reagents: NaNH2, NH3, ethere |
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Preparation of Alkynes by elimination
|
yields alkynes through doubledehydrogenation + 2HX
reagents: 3 eq. NaNH2, NH3 |
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Hydrogenation of Alkynes
|
yields alkanes
reagents: H2, Pd/C |
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Lindlar's Catalyst to Alkynes
|
yields CIS-ALKENE
reagents: H2, Lindlar's |
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Metal Ammonia Reduction of Alkynes
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yields TRANS-ALKENE
reagents: Na, NH2, HOC(CH3)3 |
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HX to Alkynes
|
yields geminal dihaloalkane in excess HX
yields trans-alkene with equal HX |
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HBr to Alkyne
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yields trans-alkene with Br
reagents: ROOR anti-Markovnikov |
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Hydration of Alkyne
|
yields enol/keto tautomerization
results in alkyl aldehyde/ketones reagents: HgSO4, H2SO4, H20 |
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X2 to Alkyne
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yields tetrahaloalkanes in excess X2
yields trans-alkene with equal X2 |
|
ozonolysis of Alkynes
|
yields carboxylic acids
reagents: O3, Zn |
|
Hydroboration oxidation of Alkynes
|
yields aldehydes of ketones
reagents: BH4, THF, NaOH, H20, H202 |
|
NBS to cyclohexene
|
yields anti-Markovnikov addition of Br
reagents: NBS, light, CCL4 |
|
which orbitals do diene/dienophile interacts?
which represent e- withdrawing, e-donating? |
diene: HOMO, e-donating
dienophile: LUMO, e-withdrawing (good dienophiles are conjugated carbonyls) |
|
Huckle's Rules
|
4n+2 pi electrons
planar conjugated |
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Birch Reduction of Benzene
|
yields nonconjugated diene
reagents: Na(0), NH3, (H3C)3COH |
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Free radical halogenation of alkylbenzene
|
yields substitution at benzylic hydrogen only
reagents: NBS, light, ROOR |
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oxidation of alkylbenzenes
|
results in carboxylic acids (benzoic acid)
reagents: KMnO4 or Na2Cr2O7, H2SO4 cleaves everything past benzylic carbon, replaces with COOH |
|
aromatic ions
|
cyclopropenyl cation
cyclopentadienyl anion cycloheptatrienyl cation |
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nitration of benzene
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reagents: HNO3, H2SO4, H20
|
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sulfonation of benzene
|
SO3, H2SO4, H20
|
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halogenation of benzene
|
X2, FeX3
|
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Friedel-Crafts Alkylation
|
removes chloride from alkane, attaches onto benzyl
AlCl3 *rearrangement possible) |
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Friedel-Crafts Acylation
|
removes chloride from carbonyl, attaches onto benzyl
AlCl3 |
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Synthesis of Alkyl benzenes
|
First, undergo Friedel-Crafts acylation
Then, reduce carbonyl (removes C=O) through Zn(Hg), HCl or H2NNH2, KOH Yields Alkylbenzene |
|
patterns for electrophilic substitution
|
e- donating - activating - ortho,para director
e-withdrawing - deactivating - meta director (exception halides) meta-directors: any CARBONYL attached to benzene, _ C=N CF3 NO2 |
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preparation of organometallic compound
|
alkyl halide with 2 metal eq.
RCH3Cl + 2M yielids RCH3M |
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synthesis of alcohols using grignard
|
grignard reagents react with aldehydes, ketones, esters to afford alcohols
aldehydes afford 2* ketones afford 3* esters afford 3* reagents: MgBr, ether/THF |
|
synthesis of acetylenic alcohols
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rxn. first btwn terminal acetylene and RMgBr to yield acetylide anion
acetylide anion reacts with carbonyl to form alcohol reagents:MgBr, ether/THF, H20 |
|
alkane synthesis through organo copper reagents
|
alkyl lithium reacts with copper halide to produce lithium dialkyl cuprate, which reacts with alkyl halid to produce alkanes by C-C bond formation
R2CuLi + R'X yields RR' reagents: ether |
|
cyclopropane formation
|
addition of carbon ring to alkene
using carbenes - reagents CHCl3, KOH (yeilds dicholorocyclo) using organozinc reagents ZnCu, CH2I2, ether |
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synthesis of alcohols by reduction of aldehydes and ketones
|
adding metal hydride (H:-)
reduces aldehydes to 1* alcohols reduces ketones to 2* alcohols reagents: NaBH4, LiAlH4 ether then H30+ |
|
synthesis of alcohols by reduction of esters and carboxylic acids
|
reduces to 1* alcohols
reagents: ONLY LiAlH4 ether then H30+ |
|
synthesis of alcohols from epoxides
|
reduces to 1* alcohol
reagents: R-MgBr+ yields: HO-CH2-CH2-R |
|
synthesis of diols
|
results in vicinal, syn addition
reagents: OSO4, (CH3)3COOH, tBtOH |
|
synthesis of ethers BY alcohols
|
alcohols
reagents: H2SO4 |
|
synthesis of esters
|
add alcohols with carboxylic acid
ROH + R'COOH -> RCOOR' reagents: HA, H2SO4 can also be formed via rxn. of acyl chloride or acid anhydride w/ an alcohol RCOCl + HOR' -> RCOO'R' reagents: pyridine |
|
esters of inorganic acids
|
nitric acid + alcohol
sulfuric acid + alcohol |
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oxidation of alcohols
|
2* alcohols oxidized to ketones
1* alcohols usually oxidized to carboxylic acids reagents: KMnO4/Na2Cr2O7, H2SO4 1* alcohol can oxidize to aldehyde w/t PCC or PDC reagents |
|
oxidative cleavage of vicinal alcohols
|
two R2COH bonds cleave as well as C-C bond btwn and form C=0 bonds.
reagents: NaIO4/HIO4 |
|
thiols
|
RSH + R'X yield RSR'
reagents: NaF, THF |