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Organic 2 Quiz

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Reaction Map of first semester organic reactions– Wiskur Spring 2012
HO

R X* R W* BrMg

X* W* Li R V* U* R or Cl) Br ( R I K H J G Y* F RO D Nuc R Br R R HO R OH V U R RO R L HO R

O Nuc R R Nuc X Br W R R M N Br R R H R O O H A* H Br R R Br (or Cl) OH Br O G* F* C* B* R O OH R D* H I* H* O R S* R O OH Br Y R Z J* R P* R* R R R R R L* R K* N* R M* Br R O* Br R O H T* Br Br R Br Q* Br Br R Br Br

O R O R S O O R

B A C

HO R

O P Q T S R HO R Br

A. LiAlH4 or NaBH4 (Chapter 12) B. PCC or KMnO4 or H2CrO4 (Chapter 12) C. RSO3Cl, pyridine (Chapter 11) D. Nucleophile (Chapter 11) E. Not on chart F. 2ROH, H2SO4 or RX, RONa (Chapter 11) G. H2SO4/H2O or 1) Hg(OAc)2/ H2O, 2) NaBH4 (oxymercuration notes only) (Chapter 7) H. PBr3 or SOBr2, Et3N (Chapter 11) I. H2O (Chapter 6) J. HBr (Chapter 7) K. Strong base (ex. KOtBu) (Chapter 6) L. Br2/H2O (Chapter 7) M. mCPBA (Chapter 11/12) N. H2/ Pd or H2/ Pt or H2/ Ni (Chapter 4) O. Br2 (Chapter 8) P. 1) BH3, 2) NaOH/ H2O2 (Chapter 8) Q. 1) O3, 2) CH3SCH3 (Chapter 8) R. HBr / peroxides (Chapter 10) S. Br2/H2O or chlorohydrin Cl2/H2O (Chapter 8) T. Br2, light (or heat) or NBS / light (or heat) (Chapter 10 notes/ Chapter 13 book) U. 1) OsO4, 2) NaHSO3 / H2O (Chapter 8) V. H2SO4/ROH (Chapter 8/11) W. NaOH, H2O (Chapter 11) X. Good nucleophile (Chapter 11) Y. Acid catalyzed – Nuc/ H2SO4 (Chapter 11) Z. Br2, light (or heat) A*. PBr3 or SOBr2, Et3N (Chapter 11) B*. KMnO4 or H2CrO4 (Chapter 12) C*. LiAlH4 (Chapter 12) D*. KMnO4 or H2CrO4 (Chapter 12) E*. Not on chart F*. PCC (Chapter 12) G*. NaBH4 or LiAlH4 (Chapter 12) H*. 2 equiv NaNH2 (Chapter 7)

I*. H2/ Pd/CaCO3 or H2/Ni2B orNa°/ NH3 (l) (Chapter 7) J*. H2/ Pd or H2/ Pt or H2/ Ni (Chapter 4) K*. H2/ Pd/CaCO3 or H2/Ni2B (Chapter 7) L*. Na°/ NH3 (l) (Chapter 7) M*. Hg(OAc)2/ H2SO4/ H2O or 1) BH3, 2) NaOH/ H2O2 (Chapter 8) N*. 1.) NaH, 2.) (RX primary) (Chapter 7) O*. Br2 (1 equiv) (Chapter 8) P*. HBr (Chapter 8) Q*. Br2 (excess) (Chapter 8) R*. 1) B(sia)2H, 2) NaOH/ H2O2 (Chapter 8) S*. Hg(OAc)2/ H2SO4/ H2O (Chapter 8) T*. HBr (Chapter 8) U*. Mg (metal), Et2O (Chapter 12) V*. Li (metal), Et2O (Chapter 12) W*. Acidic proton
O

X*. 1.) , 2.) dilute acid Y*. Conc. H2SO4/heat (Chapter 7)

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