Which reagents follow Markovnikov's Rule? Reagents sheet provided on exam. Some changes to the reagent sheet may occur. NaOMe КОBu or KOC(CH)з 1. TsCl, pyridine 2. nucleophile HBr H;SO: (concentrated, sometimes shown with heat or A) NaNH (or NaH) NANH2 (excess) 1. NANH2 (3 eq) H2, Pt (or Pd) H2, Lindlar Na, NH3 HgSO4, H,SO4, H2O 1. R,BH (like (sia),BH or 9-BBN) 2. H,O2, NaOH HBr (1 eq) 2. Н.О H2, Pt (or Pd) X2 like Br2 Br2, H,O H2SO4, H2O (or "dilute sulfuric acid," or H;O*, or H*, H2O) HBr 1. Hg(OAc), H,о 1. BH, | 1. O. | 1. OsO4 mcpba (or RCO,H) HBr (excess, or 2 eq) Br2 (1 eq) Br, (excess, or 2 eq) Br2, hv 2. NaBH4 2. H,О, NaOH 2. DMS ((CH3)2S) (or Zn/H2O) 2. NaHSO3, H2O HBr, ROOR

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Which reagents follow Markovnikov's Rule?
Reagents sheet provided on exam. Some changes to the reagent sheet may occur.
NaOMe
КОBu or KOC(CH)з
1. TsCl, pyridine 2. nucleophile
HBr
H;SO: (concentrated, sometimes shown with heat or A)
NaNH (or NaH)
NANH2 (excess)
1. NANH2 (3 eq)
H2, Pt (or Pd)
H2, Lindlar
Na, NH3
HgSO4, H,SO4, H2O
1. R,BH (like (sia),BH or 9-BBN) 2. H,O2, NaOH
HBr (1 eq)
2. Н.О
H2, Pt (or Pd)
X2 like Br2
Br2, H,O
H2SO4, H2O
(or "dilute sulfuric acid," or H;O*, or H*, H2O)
HBr
1. Hg(OAc), H,о
1. BH,
| 1. O.
| 1. OsO4
mcpba (or RCO,H)
HBr (excess, or 2 eq)
Br2 (1 eq)
Br, (excess, or 2 eq)
Br2, hv
2. NaBH4
2. H,О, NaOH
2. DMS ((CH3)2S) (or Zn/H2O)
2. NaHSO3, H2O
HBr, ROOR
Transcribed Image Text:Which reagents follow Markovnikov's Rule? Reagents sheet provided on exam. Some changes to the reagent sheet may occur. NaOMe КОBu or KOC(CH)з 1. TsCl, pyridine 2. nucleophile HBr H;SO: (concentrated, sometimes shown with heat or A) NaNH (or NaH) NANH2 (excess) 1. NANH2 (3 eq) H2, Pt (or Pd) H2, Lindlar Na, NH3 HgSO4, H,SO4, H2O 1. R,BH (like (sia),BH or 9-BBN) 2. H,O2, NaOH HBr (1 eq) 2. Н.О H2, Pt (or Pd) X2 like Br2 Br2, H,O H2SO4, H2O (or "dilute sulfuric acid," or H;O*, or H*, H2O) HBr 1. Hg(OAc), H,о 1. BH, | 1. O. | 1. OsO4 mcpba (or RCO,H) HBr (excess, or 2 eq) Br2 (1 eq) Br, (excess, or 2 eq) Br2, hv 2. NaBH4 2. H,О, NaOH 2. DMS ((CH3)2S) (or Zn/H2O) 2. NaHSO3, H2O HBr, ROOR
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