Organic Chemistry Reagents and Products – Flashcards
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Add OH antimarkov
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1. BH3 2. NaOH, H202 anti mark racemic mixture **works with alkYnes too, gives C-OH, then O=C**
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Add two Br to alkene (TRANS)
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Br2
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Add Br and OH to alkene (TRANS)
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Br2, H20
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To make O=C out of C=C (anti)
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1. BH3 2. NaOH, H202
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Adding Br out of nowhere
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Br2, hv
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Adding CN to replace Br
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DMSO, KCN
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Make O=C out of OH
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CrO3, pyridine
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Go from MgBr to CO2H
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1. CO2 2. H30+
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H2 and metal will take alkyne to
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alkane
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H2 and lindlars will take alkyne to
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alkene
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lindlars will make it cis/trans
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cis
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Br to add markov
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HBr
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Get alkene with Br markov from alkyne
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HBr
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Add Br anti
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HBr, H2O2
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Switch OH to Br
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HBr
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Make OH add markov
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1.Hg(OAc), H20 2. NaBH4
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Make OH into carboxylic acid
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KMnO4
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Cleave with OH's on ends
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KMnO4, H30
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Make Br eliminate anti
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KOtBu
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Go from carboxylic acid to OH
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LiAlH4
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Making rings
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MCPBA
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Reducing alkyne to alkene (TRANS)
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Na, NH3(l)
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Take benzene to only two double bonds (evenly spaced)
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Na, NH3(l)
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C=O to C-OH
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NaBH4
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aldehyde to C-OH
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NaBH4
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Add OH markov
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1. Hg(OAc), H20 2. NaBH4 ANTI NO rearrangements
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Make alkyne a negative species
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NaNH2
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Make two Brs collape to make alkyne
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NaNH2
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Make Br eliminate markov
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NaOH, H20, heat
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Add Br and OH to alkene (TRANS)
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NBS, H20
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Cleave and leave hydrogens on end
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1. O3 2. Zn, acetic acid
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Adding chain antimarkov
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1. Cu(+chain) *dont forget to write Li+also** 2. H30+
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Adding chain to Cl
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Cu(+chain) **dont forget to write Li+ also**
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Add two OH (CIS) to alkene
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OsO4
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Get OH (primary) to aldehyde
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PCC
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Get OH (secondary) to ketone
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PCC
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Go from Br to OH
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-OH, H20
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Go from OH to Br
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HBr
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Delete C-C bond (replace with H)
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NaBH4
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Make alkane to alkYne
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-OH
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Adding strong acid will make ___ elim
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markov
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make C-OH into C=O
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Na2Cr2O7, H2SO4
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Add OH markov to alkene
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H30+ and H20 *ORRRR* Hg(OAc),H20, NaBH4
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Add OH antimarkov to alkene
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1. BH3, THF 2. H202, NaOH, H20 No rearrangements SYN
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Add O chain markov to alkene
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1. Hg(OAc), H(O-chain) 2. NaBH4
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Acidic epoxide opening will make existing methyl
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switch stereochem
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Basic epoxide opening will make existing methyl
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keep stereochem
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Acidic epoxide opening
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H30+, H20
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Basic epoxide opening
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1. KOH 2. H30+
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form ring of carbon
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CH2I2, Zn(Cu)
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form ring of chlorocarbon
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CHCl3, KOH
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make a cis OH from alkene
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1. OsO4 2. H202
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if you have two pi bonds, 1-2 and 1-4 addition achieved by
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HCl
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thermodynamic product will add to the __ position, and the pi bond will _
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4 position, move away
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alkYne to aldehyde (C=O will be on most subst C)
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1. disamylborane 2. KOH, H202
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to get cl and oh from alkene (TRANS)
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H20, Cl2
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alkYne to alkene (CIS)
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H2, lindlars
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alkYne to alkene (TRANS)
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Na0, NH3(l)
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add any chain to LG spot
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1. Mg, Et20 (will give MgLG) 2. neg species chain
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Turn C=O to antennae OH + methyl
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1. Li-Me 2. H20
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Eliminate Br to get pi bond
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KOt-Bu
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Eliminate OH to get pi bond
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H30+
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Br to OH switch
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KOH
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To add o-chain or OH markov with NO subst
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1. Hg(OAc)2, H20 or H(o-chain) 2. NaBH4
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to make --OH go to -CO2H
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KMnO4
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reduce alkene to chain (1,4add)
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chain+CuLi, H30
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To use MgBr, must have ___ on molecule already, then chain with ___
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Br, Br---
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Add OH antimark
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1. Bh3 2. NaOH, H202
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the major product for an elimination reaction is at the
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most substituted alkene
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1 Degree Substrate
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promotes sn2 or elimination - only if base is bulky
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2 degree substrate with weak base and protic solvent, heat
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E1 with carbocation
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3 degree substrate with protic and weak nucleophile
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Sn1, C+, racemization
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3 degree with aprotic, strong bulky base, heat
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E2, anti-periplanar
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too add BH2 and H to alkene
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BH3
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POCl3 and pyridine
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Dehydration
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2 degree protic with weak nuc-
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Sn1, C+, racemization
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Br2, H20, and NaH
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Forms epoxide
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Strong Nucleophile and Strong Base can..
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Lead to Sn2 or E2
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3 degree with protic and weak base, heat
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E1, C+, best with 3 degree
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DMS, NMS, H20
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Adds Br and OH
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TSCl, pyridine
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adds OTS
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HC---C:-
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can open rings and add to them
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2 degree with aprotic, strong bulky base, heat
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E2 , anti-periplanar
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2 degree with aprotic and strong nuc-
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Sn2, inversion
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Degrees of Unsaturation
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2C+2+N-H-X/2
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KMnO4, H20
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cleaves double bond of alkene to form c. acids, ketones, aldehydes
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OsO4 NaHSO3 H20
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Oxidation Agent Syn Addn.
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HX to alkynes
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Mark 4X added Geminal Dihalides
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mCPBA to alkene
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forms epoxide
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PPC
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1 degree alcohol to aldehyde 2 degree alcohol to ketone
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KMnO4 or H2CrO4 to 1 degree alcohol
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oxidize 1 degree alcohol to carboxylic acid
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H2CrO4 to 2 degree alcohol
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forms ketone
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KMnO4, NaOH, H20
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Adds OH, OH SYN
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O3 Zn, H3O+
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cleaves C--C to form aldehydes/ketones
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K2CrO7
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oxidizing agent, converts alcohols to aldehydes
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RCO3H H20 to alkene
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epoxidation followed by ring opening
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Halohydrin to epoxide
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add base
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Internal alkene plus H20/H2SO4 or BH3/H2O2/OH-
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ketone
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Oxidation of secondary alcohol
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add Cr6+ reagent PCC CrO3/H2SO4
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Oxidation of primary alcohol
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add Cr6+ reagent CrO3/H2SO4
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Halogenation of Alkenes
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Type: addition Reagents: X₂ Stereochemistry: racemic mixture, anti addition
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Halohydrin Formation of Alkenes
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Type: addition Reagents: X₂, H₂O Stereochemistry: racemic mixture, anti addition
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Hydroboration-oxidation
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Type: addition Reagents: BH₃∙THF, H₂O₂, NaOH Stereochemistry: racemic mixture, syn additon Regiochemistry: Anti Markovnikov
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ROH plus NaH and RX
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Ether
