Organic I Reactions | CH 4513 - Organic Chemistry I, Quizzes of Organic Chemistry

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TERM 1 Instructions DEFINITION 1 1) Type of Reaction2) Type of addition a) Markovnikov or Anti-Markovnikov Addition b) Whether Carbocation Rearrangement is Possible c) Typically considered in a ring: Syn addition, Anti addition, or Racemic 3) Type of Product TERM 2 Alkene + 1) Hg(OAc)2, H2O 2) NaBH4, NaOH DEFINITION 2 Mercuration-DemercuationMarkovnikov Addition; NO Carbocation Rearrangement; Anti-addition; Produces: Alcohol TERM 3 Alkene + 1) Hg(OAc)2, R-O-H 2) NaBH4, NaOH DEFINITION 3 Alkylmercuration-DemercuationMarkovnikov AdditionProduces: Ether TERM 4 Alkene + 1) BH3, THF 2) H2O2, NaOH DEFINITION 4 Hydroboration-OxidationAnit-Markovnikov Addition; NO Carbocation Rearrangement; Syn addition; Produces: Alcohol TERM 5 Alkene + 1) X2 2) H2O DEFINITION 5 Halohydrin FormationAnti-Markovnikov Addition of the Bromine; No Carbocation Rearrangement; Anti-Addition; Produces: halohydrin with the alcohol added to the more substituted carbon TERM 6 Alkene + X2 DEFINITION 6 Electrophilic Addition of Bromine or ChlorineNOT a type of Markovnikov addition; NO Carbocation Rearrangement; Anti- Addition; Produces: Vicincal dihalide Cis-alkene into racemic mixture of alkylhalide enantiomeres. Trans-alkene into meso alkylhalide solution. TERM 7 Alkene + H-X DEFINITION 7 Acid-Catalyzed HydrationMarkovnikov Addition; Carbocation Rearrangement Possible; No syn or anti addition; Produces: Alkyl Halide TERM 8 Alkene + H3O+ DEFINITION 8 Acid-Catalyzed HydrationMarkovnikov Addition; Carbocation Rearrangement Possible; No syn or anti addition; Produces: Alcohol TERM 9 Alkene + 1) KMnO4, -OH 2) COLD, H2O DEFINITION 9 Dihydroxylation of AlkeneNOT a type of Markovnikov addition NO Carbocation Rearrangement Syn Addition Produces: Vicinal Diol TERM 10 Alkene + 1) OsO4, pyridine 2) Na2So3/H2O OR NaHSO3/H2O DEFINITION 10 Dihydroxylation of AlkeneNOT a type of Markovnikov addition NO Carbocation Rearrangement Syn Addition Produces: Vincinal Diol TERM 21 HBr + R-O-O-R DEFINITION 21 Bromine Radical FormationBr will add to the less substituted carbon in a hydrocarbon. TERM 22 R-O-O-R + Heat DEFINITION 22 Oxygen Radial FormationR-O-O-H can lead to an hydroxyl radical. TERM 23 Alkene + H2 (excess) or Alkyne Ni, Pt, or Pd DEFINITION 23 Hydration of Alkene or AlkyneNOT a type of Markovnikov Reaction; NO Carbocation Intermediate; Syn addition; Produces: Alkane TERM 24 X2 + Heat or UV light DEFINITION 24 Halide Radical FormationCl is unselective. Br is selective and will add to the more substituted carbon hydrocarbon. TERM 25 Remove Protecting Group DEFINITION 25 Fluorine Anion TERM 26 Alcohol + HX DEFINITION 26 Formation of Alkyl HalideMarkovnikov Addition; Carbocation Rearrangement Possible; Racemic; Produces: Alkyl Halide TERM 27 Alcohol + H2SO4 or H3PO4 Heat DEFINITION 27 Acid Catalyzed DehydrationZaitsev's Rule; Most stable alkene formedElmination not Addition; Produces: Alkene TERM 28 Primary Alcohol + H2SO4 Low temp DEFINITION 28 Synthesis of EthersIn a solution of one alcohol, a symmetric ether is formed. If an alkene is added, an ether will form. Recall that an ether can also be formed from alkoxymercuration-demercuration of an alkene in the presence of R-O-H.Produces: Ether (depending on other chemicals present) TERM 29 Alcohol + PBr3 DEFINITION 29 Formation of Alkyl HalideMarkovnikov Addition; NO Carbocation Rearrangement; Neither; Produces: Alkyl Halide with inversion of configuration TERM 30 Alcohol + 1) NaH 2) RX DEFINITION 30 Williamson ReactionThe substrate (# 2 on front) must be unhindered and bear a good leaving group.SN2 Reaction (inverted stereochemistry)Produces: Asymmetric Ether TERM 31 Alcohol + SOCl2 DEFINITION 31 Formation of Alkyl HalideMarkovnikov Addition; NO Carbocation Rearrangement; Neither; Produces: Alkyl Halide with inversion of configuration TERM 32 Alkene + Peroxyacid DEFINITION 32 Synthesis of EpoxideStereochemistry of alkene is retained. (Cis-alkene gives cis- epoxide). An example of a peroxyacid in mCPBA (meta-chloroperoxybenzoic acid).Produces: Epoxide TERM 33 Epoxide + Acid DEFINITION 33 Acid-Catalyzed Ring-OpeningThe nucleophile adds to the more substituted carbon, and the neutralized oxygen (hydroxl group) is on the less substituted carbon. The nucleophile and hydroxyl group are trans. TERM 34 Alkene + KMnO4 H2O/-OH DEFINITION 34 Syn-Dihydroxylation via EpoxidesThe KMnO4 creates a ring that is later cleaved into hydroxyl groups on the former alkene. These hydroxyl groups are cis.Produces: cis-diol TERM 35 Epoxide + Base DEFINITION 35 Base-Catalyzed Ring-OpeningThe nucleophile adds to the less substituted carbon, and the neutralized oxygen (hydroxl group) is on the moresubstituted carbon. The nucleophile and hydroxyl group are trans. TERM 46 Alcohol + KMnO4 DEFINITION 46 KMnO4 (Oxidizing Agent)Primary Alcohol to Carboxylic Acid Secondary Alcohol - Ketone (depends.... MAYBE) Tertiary Alcohol - No Reaction TERM 47 Epoxide + RMgBr in 1) Ether solvent 2) H2O/acid DEFINITION 47 Grignard Reagent ReactivityEpoxide into Alcohol TERM 48 Ketone + RMgX in 1) Et2O 2) H3O+ DEFINITION 48 Grignard Reagent ReactivityKetone into Tertiary Alcohol TERM 49 Aldehyde + RMgX in 1) Et2O 2) H3O+ DEFINITION 49 Grignard Reagent ReactivityAldehyde into Secondary Alcohol TERM 50 Ester + RMgX in 1) Et2O 2) H3O+ DEFINITION 50 Grignard Reagent ReactivityEster into Tertiary Alcohol TERM 51 Which Reaction Will Happen? Primary Halide DEFINITION 51 Mostly SN2/E2Mostly SN2Exception: Strong Bulky Base -> E2 TERM 52 Which Reaction Will Happen? Secondary DEFINITION 52 Mostly SN2/E2Prefer SN2 with weak bases; Prefer E2 with strong bases; TERM 53 Which Reaction Will Happen? Tertiary Halide DEFINITION 53 SN1, E1, and E2NEVER SN2; Low temperatures favor SN1; Higher temperatures favor E1/E2: 1) Weak base -> E1 2) Strong base -> E2 TERM 54 Strong or Weak? A) Tert-butanol B) CN- C) RO- D) I- E) RCO2- DEFINITION 54 A) Weak Acid -> Strong Bulky Conjugate Base (CH3)3CO-B) Weak BaseC) Strong Base (Ex. Conjugate Acid of ethanol -> C2H5O-)D) Weak Base -> Strong Conjugate Acid (HI)E) Weak Base -> Strong Conjugate Acid (H2CO4)