Organic Chemistry II

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H2, Pd/C
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C=C –> C-C; ketone –> secondary ROH; aldehyde –> primary ROH; NO2 –> NH2; CN–> NH2; imine –> NH2; 1 eq. will selectively reduce a C=C before a C=O, but excess will reduce both
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HNO3, H2SO4
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Adds NO2 to Benzene (nitration)
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H2SO4, heat; H2O, heat
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1. addition of SO3H to benzene (sulfonation) 2. removes SO3H from benzene (desulfonation)
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Cl2, AlCl3
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add Cl to aromatic ring (halogenation); can also use Br2 and AlCl3; EAS
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Br2, FeBr3
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add Br to aromatic ring (halogenation); can also use Cl2 and FeCl3; EAS
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RCOCl, AlCl3
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adds a carbonyl group directly to benzene (Friedel-Krafts Acylation)
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RCl, AlCl3
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adds an R group directly to benzene (Friedel-Krafts Alkylation); Carbocation Rearrangement
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Zn(Hg), HCl
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reduces carbonyl to an alkane using acid (Clemmenson Reduction)
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H2NNH2,-OH, heat
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reduces carbonyl to an alkane using a base (Wolff-Kishner Reduction)
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Sn, HCl, -OH
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reduces nitrobenzene to aniline with intermediate (NO2 –> NH3+ –> NH2)
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NaNO2, HCl
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converts PhNH2 –> PhN2 (aniline –> aryldiazonium salt)
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CuCl
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substitutes PhN2 –> PhCl; allows you to add a halogen para as opposed to halogenation which gives 2 products: ortho and para
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CuCN
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substitutes PhN2 –> PhCN
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KI
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substitutes PhN2 –> PhI (Iodobenzene)
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HBF4
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substitutes PhN2 –> PhF (Flourobenzene)
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H3PO2
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reduction of PhN2 –> benzene
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H2O, warm
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substitutes PhN2 –> PhOH (Phenol)
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KMnO4, acid
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PhCH3 –> PhCOOH; can also use NaCr2O7; reacts with any R group with hydrogens on its benzylic carbon to form benzoic acid; tertiary R group –> No Reaction
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NBS, hv
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adds a Br to the benzylic carbon; adds a Br to an alkane; PhCH2R –> PhCH(Br)R
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Madison
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The best neice in the whole entire world ever!!! 🙂
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ortho/para bromination of phenol
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Phenol + Br2 –> ?
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ald/ket + -OH, H2O
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a gem-diol forms where the carbonyl oxygen was (formation of hydrate); H+ and water can also be used and it can reverse the reaction
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ald/ket + H+, ROH (2 equiv.), H2O
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an acetal/ketal forms where the carbonly oxygen was (2 OR groups add to the carbonyl C); if a diol is used instead, a cyclic acetal/ketal will form; H+ and water will reverse the reaction
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OHROH, TsOH
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forms a cyclic acetal (protecting group) on the more reactive carbonyl group; acid and water will unprotect the carbonyl group
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ald/ket + NaCN, HCl
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CN is added to the carbonyl carbon and =O is reduced to -OH; basic conditions will reverse the reaction
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RCN + H+,H2O, hv
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RCN –> COOH (carboxylic acid is formed)
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RCN + H2, Raney Ni
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RCN –> RNH2 (primary amine is formed); ketone –> secondary alcohol
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CrO3, H2SO4
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primary alcohol –> COOH (under aq. cond’ns); secondary alcohol –> ketone; aldehyde–> COOH (under aq. cond’ns); phenol —> benzoquinone; gem-diol –> COOH; can also use K2CrO7
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PCC
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primary alcohol –> aldehyde (Swern Oxidation is better)
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1) DMSO+ ClCOCOCl 2) Et3N
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primary alcohol –> CHO; secondary alcohol–> ketone (Swern Oxidation)
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-OH, HOOH
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CHO –> COOH;
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RCOOOH
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CHO –> COOH; ketone –> ester (Baeyer-Villager Oxidation); alkene –> epoxide
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O3, DMS
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alkene –> ketone + CHO
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O3, DMS, HOOH, H+
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alkene –> ketone + COOH
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OsO4 or cold KMnO4 (aq.)
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H2C=CH2 –> OHCH2CH2OH; forms a vicinal diol (Dihydroxylation of Alkenes)
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HIO4, H2O
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cleavage of diols –> aldehydes or ketones
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LiAlH4 or NaBH4, H2O, H+
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ketone –> secondary OH; ester –> primary OH; CHO –> primary alcohol; COOH –> primary alcohol; CN –> NH2; selectively will reduce C=O before C=C
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Mg
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CH3CH2Br –> CH3CH2MgBr;
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Li
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CH3CH2Br –> CH3CH2Li
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CuI
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CH3CH2Li –> (CH3CH2)2CuLi
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RBr, RCl
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(CH3CH2)2CuLi –> CH3CH2R
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=CHCl (vinyl halide)
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CH3CH2 –> CH3CH2CH=CH2
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RMgBr or RLi or R2CuLi, H2O, H+
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aldehyde –> secondary alcohol; ketone –> tertiary alcohol; epoxide –> alcohol (both reduction and addition of halogen or R group to the epoxide); will react with aldol product at carbonyl (not alkene) and form OH and add a R group
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Ph3P:-CH2(-)R (ylide)
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ald/ket –> alkene; CH3CH2CHO –> CH3CH2CH=CH2R
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SOCl2 or PCl3 or PBr3
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forms an acid chloride
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NaBH3CN or H2 + Pd/C or NaBH(OCOCH3)
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reduces primary imine –> NH2; reduces secondary imine –> NHR; reduces ald/ket + RNH2 –> RHNR’
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ald/ket + R2NH, HCl
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CHO + R2NH –> R2NC=C(R or H); forms an enamine at the a-carbon of carbonyl; reaction can be reversed with H+ and water
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ald/ket + RNH2, HCl
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CHO + RNH2 –> CH=NR; forms an imine; reaction can be reversed with H+ and water
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1) DIBAL + CN 2) NaOH, H2O
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reduces R’CN –> R’C(=NH)R; reduces to an imine
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1) RMgBr or RLi 2)NaCNBH3
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reacts the same as LiAlH4 and reduces RCN –> RNH2R”
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1)R”MgBr or R”Li + CN 2) NaOH, H2O
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forms imine (reduces R’CN –> R’C(=NH)R”)
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1)R”MgBr or R”Li + CN 2) H2O
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reduces imine to amine; reduces R’C=NR –> R’C(NR)R”
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!) DIBAL 2) H2O, H+
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RCN –> RCHO
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1) RMgBr or RLi + R’CN 2) H2O, HCl
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R’CN –> R’C(=O)R; Nitrile –> ketone
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1) CH3Br or 1) CH3Br 2) Ag2O 2) NaOH, H2O 3) heat
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R”CH3CH2NR3 –> R”CH=CH2; forms alkene from quaternary ammonium salts (Hoffmann Elimination)
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ald/ket + acid or base
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CH2CHO –> H2C=COH; CH3C(=O)R –> CH2=C(OH)R; keto-enol tautomerization
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HCl, H2O
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addition of water to an alkyne to form keto-enol form of ald/ket
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H3CC(=O)CH3 + LDA
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H3CC(O-)=C; forms enolate; forms one product for aldol rxn

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