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26 Cards in this Set

  • Front
  • Back

1* ROH, HX

make alkyl halide via SN2

2*/3* ROH, HX

make alkyl halide via SN1

ROH, PX3

make alkyl halide via SN2 w/ inversion of configuration

Carbonyl, NaBH4, MeOH

Reduces ketones and aldehydes to alcohols

ROH


dilute H2SO4 (H3O+,H2O)

OH adds to the most sub C w/ R

ROH


1.Hg(OAc)2, H2O


2.NaBH4

OH adds to the most sub C w/out R

ROH


1.BH3-THF


2.H2O2, NaOH

OH adds to the least sub C

Carbonyl


1.xs LAh


2. H2O

Reduces esters, carboxylic acids, ketones, and aldehydes to alcohol (ROH)

Carbonyl


1. H2, Pt, high P

Reduces everything

ROH


1.RCO3H (mCPBA)


2. H3O+

Trans Diol

ROH


1.KMnO4, NaOH, Cold

Syn Diols

ROH


1. OsO4, NMO

Syn Diols

1* RX + charged Nu-

SN2: Nu- adds to least sub C

3* RX + neutral Nu-

SN1: Nu- adds to most sub C

Carbonyl


1. RMgX, THF


2.H2O

3* alcohol

ROH


1. SOX2


2. Py or NR3

ROH --> RX via SN2




*only used with 1 or 2 ROH


*SO2 (g) bubbling out = driving force

ROH + TsCl, NR3 or Py

Makes OTs (good LG)




*no inversion

OTs + Nu(-)

SN2

OTs + base

E2

ROH + H3O+

Make alkene




2 and 3 ROH = E1


1 ROH = E2 (don't make 1 carbocation)

ROH + POCl3, pyr or NR3

dehydration of ROH = make alkene via E2 of H2O

1* ROH + DMP or PCC

aldehyde

1* ROH + Chromic Acid (K2Cr2O7, H2SO4, H2O)

carboxylic acid

2* ROH + DMP, PCC, or Chromic Acid

ketone

3* ROH + DMC, PCC, or Chromic Acid

DOES NOT OCCUR

ROH + TMSCl, base (NR3)

add protecting group (OTMS)