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Synthetic chart

Alkanes Cl2 or Br2 plus light or

H2, Pd/C Alkynes H2, Pd/C Polymers R-O-O-R


H2, Lindlars catalyst

Haloalkanes

HX or X2 X = Cl, Br, I NaOH (cold, dilute), or H2O H3O+**

Alkenes

Mg, Et2O*

conc. H2SO4,

R-MgX
RMgX can go to each degree of alcohol depending on the carbonyl reagent used (H2CO, RHCO, R2CO)

Alcohols 1o 2o 3o MnO4-, Cr2O72- or PCC,CH2Cl2* 1. NaBH4 2. H3O+** Ketones 1. R-MgX, Et 2O* 2. H3O+ **

1. NaBH4 PCC, 2. H3O+ ** CH2Cl2* Aldehydes 1. R-MgX , Et 2O* 2. H3O+ **

MnO4or Cr2O72CO2

MnO4or Cr2O72-

1. R-MgX , Et 2O* 2. H3O+** ROH, H+ H3O+**,

Carboxylic acids

Ester

ROH
H3O
+

Anydride

Notes: formaldehyde only


* CH2Cl2 and Et2O are solvents, they do not participate in the reaction. ** H3O+ is dilute aqueous acid (e.g., 10% H2SO4). In some reactions, it is used for workup, in others, it is an acid catalyst.

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