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What does the reagent H2 do with a catalyst of Pt/C Pd/C or Ni? (alkene)
- Adds two H's to an alkene and makes it an alkane.
- Syn-addition
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What does the reagent HBr or HCl do? (alkene)
- It adds H and Br/Cl to an alkene and makes it an alkane.
- Markovnikov (Br/Cl to the most substituted).
- Rearrangement is possible.
- Random Racemization.
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X2, CH2Cl2 (alkene)
- Adds to X's to an alkene to make it an alkane.
- Anti-addition
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X2, H2O (alkene)
- X and OH are added to an alkene and makes it alkane.
- Markovnikov (OH added to most subst.)
- Anti-addition
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X2, ROH (alkene)
- Adds X and OR to an alkene making it an alkane.
- Markovnikov (OR added to most subst.)
- Anti-addition
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Br2, NaCl (alkene)
- Br and Cl are added to an alkene making it an alkane.
- Markovnikov (Cl on most subst.)
- Anti-addition
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H2O, Acid Catalyst (alkene)
- H and OH are added to an alkene making it an alkane.
- Markovnikov
- Rearrangement is possible.
- Random/racemization
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1.Hg(OAc)2, H2O/THF (alkene)
2. NaBH4
- H and OH are added to an alkene making it an alkane
- Markovnikov
- Anti-addition
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1. BH3, THF (alkene)
2. H2O2, H2O, NaOH
- H and OH are added to an alkene making it an alkane.
- Anti-Markovnikov
- Syn-addition
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ROH with Acid (alkene)
- H and OR are added to an alkene making it an alkane.
- Markovnikov
- Rearrangement possible
- Random/racemization
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1. Hg(OAc)2, ROH (alkene)
2. NaBH4
- H and OR and added to an alkene making it an alkane.
- Markovnikov
- Anti-addition
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2 eq. of HBr or HCl (alkyne)
Adds two Br or Cl to most subst. and two H's to least subst. of the alkyne bond.
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2 eq. of Br2 or Cl2 (alkyne)
Adds two Br or Cl to each side. In the intermediate they are added to make a trans product.
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1 eq. of H2O and an acid catalyst (alkyne)
Has two steps. The first step uses the eq. of H2O and makes an enol, adding an OH to the most subst. and an H to the least subst. and reducing the alkyne to an alkene. The second step is spontaneous and adds a H to the least subst. side, reduces the alkene to an alkane, and makes the bond to an O a double bond and takes away the H connected to the O.
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H2O, H2SO4, HgSO4 (alkyne)
- Alternate form of converting alkyne to enol and then to keto.
- So essentially alkyne is taken and becomes an alkane with two H's on least subst. side and a double bonded O on the most subst. side.
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1. Disiamyborane (alkyne)
2. H2O2, OH-
- The anti-mark version of the alkyne to Enol to Keto mechanism.
- Alkyne is taken and becomes an alkane with two H's on most subst. end and double bonded O on least subst. end.
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H2, Pd/C (alkyne)
reduces double and triple bonds completely to alkanes (giving H's in place of pi bonds)
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H2, Lindlar's Catalyst (alkyne)
Reduces triple bonds to double bonds with syn addition of two H's.
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Na/NH3 (alkyne)
Reduces triple bonds to double bonds with trans addition of two H's.
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NaNH2
- This is a very important one.
- It is used to deprotonate an alkyne and turn it into a strong Nucleophile.
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MCPBA
Adds O to where alkene used to be and alkane now is as a three-membered ring.
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What are common bases used for E1 reactions?
H2O, ROH
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What are common bases used in E2 reactions?
- Small bases (to be on most subst.) - OH-, CH3O-
- Bulky bases (to be on least subst.)- HOtBu, DBN, DBU
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What are common solvents for SN1?
Weak Nucleophiles-CH3OH (any ROH), H2O, etc.
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What are common solvents for SN2?
Strong nucleophiles- NaN3 with DMSO, NaOH with water, etc.
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Br2 or Cl2 and hv (light) (alkane)
Addition of Br to alkane at most subst. and Cl to either.
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NBS with light/heat and peroxide (H2O2) (alkene)
Adds Br to C next to the alkene
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HBr and peroxide (H2O2, R2O2, ROOR) (alkene)
Adds Br to least substituted and changes alkene to alkane.
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NaNH2
Strong base that is used to deprotonate an alkyne.
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Nao, NH3
- Reduces a triple bond to double bond.
- Adds H's to make trans alkene
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1. LiAlH4
2. H2O
Takes leaving group off and is replaced with H or bond moves somewhere else on Molecule.
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What are some reagents for oxidation?
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