ochem from quizlet

• 1) BH3

  2) NaOH, H2O2

  OH and H (anti MKNK)
• 1) H2SO4, H2O

  OH and H, MKNK
• HX


  addition of X and H, MKNK
• X2


  addition of X and X, anti STEREO
• X2, H2O


  addition of X and OH, MKNK (OH is substituted)
• KMnO4

  cold, dilute

  or 1) OsO4, 2) NaHSO3

  OH and OH

  C=O and OH in H2SO4

  syn STEREO
• H2/P2

  H2/Pd,Pt,C

  H2/P2 - removes one bond from alkyne

  H2/Pd,Pt,C - removes two bonds from alkyne

  syn STEREO
• HBr

  ROOR

  anti MKNK
• m-PCBA (peroxyacid)


  becomes epoxide syn

  H3O added, becomes anti STEREO
• HBr

  NaNH2

  alkyne
• alcohol to ether


  NaH, CH3I

  SN2 -> 1º/2º
• adding alkane to triple bond


  uses SN2

  1)NaNH2

  2)CH3I
• DHº


  bonds broken - bonds formed
• R-CH2-OH + PBr3


  R-CH2-Br (only use 1º/2º alcohols)
• H3C-CH2-OH + PCC


  H3C-CH=O
• reduction


  reaction that increases a compound's H-content

  reaction that decreases a compound's O-content
• limitations for grignards


  acidic groups: -OH, -NH2, -NHR, -COOH, -SO3H, -SH, -C=-C-H
• R-COO- + NaBH4


  no reaction
• R-COOR + NaBH4


  no reaction
• R-CHO + NaBH4


  R-CH2-OH 1º alcohol
• (R-)2C=O + NaBH4


  (R-)2CH-OH 2º alcohol
• R-COO- +LiAlH4


  R-CH2-OH 1º alcohol
• R-COOR + LiAlH4


  R-CH2-OH 1º alcohol
• R-CHO + LiAlH4


  R-CH2-OH 1º alcohol
• (R-)2C=O + LiAlH4


  (R-)2CH-OH 2º alcohol
• difference between anti STEREO and anti MKNK

  anti STEREO - attacks anti from each other, causes trans

  anti MKNK - least substituted alkene carbon
• staggered is ____ stable and requires ____ energy than eclipsed

  more, less
• reactions will favor anti or gauche

  anti
• stereoisomers

  same molecular formula, diff boiling/melting points (diastereoisomers, enantiomers)
• cyclopropane (60 deg), cyclobutane (90 deg), cyclopentane (108 deg) ring strain kj/mol

  115, 109, 27
• chair is ____ stable than boat

  more
• axial is ____ stable than equatorial

  less
• diastereomers


  not mirror images of each other
• enantiomers


  mirror images of each other
• what are the configs for diastereomers

  RR pair and RS pair

  SS pair and RS pair
• what are the configs for enantiomers

  RR pair and SS pair
• what are the configs for identical


  RS and RS
• methane


  CH4

  
• ethane


  C2H6

  
• propane


  C3H8