4. . How would you synthesize the following compounds from an alkene? a. b. c. d. e. f. g. h. i. j. Reagent Intermediate Product Regioselectivity Stereochemistry* Carbocation HCl, HBr halide Put the halogen on the aka (sp2 trigonal planar) Non-Stereospecific HI haloalkane more substituted carbon or possible rearrangement Carbocation H2O ROH Put the OH or OR on the or (sp2 trigonal planar) Alcohol ether Non-Stereospecific or with H2SO4 more substituted carbon possible rearrangement Cl2 Br2 Stereospecific or Cyclic halonium ion Vicinal dihalide N/A with CH2Cl2 Put OH or OR on the Cl2 Br2 or Vicinal halohydrin more substituted carbon Stereospecific or with H2O Cyclic halonium ion vicinal haloether and the halogen on the ROH or least substituted Put OH on the least 1. BH3, THF Stereospecific First step is concerted Alcohol substituted carbon - anti 2. NaOH(aq), H2O2 Markonikov H2 D2 Stereospecific or Concerted Alkane N/A with Pd/C RCO3H Stereospecific aka Concerted Epoxide N/A peroxy acid 1. O3, -78°C Aldehydes and/or Molozonide then Ozonide N/A N/A 2. (CH3)2S or Ketones Zn/CH3CO2H *Stereochemistry Considerations ⇒ - Reactions that only produce 1 asymmetric center with produce both R and S
4. . How would you synthesize the following compounds from an alkene? a. b. c. d. e. f. g. h. i. j. Reagent Intermediate Product Regioselectivity Stereochemistry* HCl, HBr or HI Carbocation (sp2 trigonal planar) possible rearrangement halide aka haloalkane Put the halogen on the more substituted carbon Non-Stereospecific H2O or ROH with H2SO4 Carbocation (sp2 trigonal planar) possible rearrangement Alcohol or ether Put the OH or OR on the more substituted carbon Non-Stereospecific Cl2 or Br2 with CH2Cl2 Cyclic halonium ion Vicinal dihalide N/A Stereospecific Cl2 or Br2 with H2O or ROH Cyclic halonium ion Vicinal halohydrin or vicinal haloether Put OH or OR on the more substituted carbon and the halogen on the least substituted Stereospecific 1. BH3, THF 2. NaOH(aq), H2O2 First step is concerted Alcohol Put OH on the least substituted carbon - anti Markonikov Stereospecific H2 or D2 with Pd/C Concerted Alkane N/A Stereospecific RCO3H aka peroxy acid Concerted Epoxide N/A Stereospecific 1. O3, -78°C 2. (CH3)2S or Zn/CH3CO2H Molozonide then Ozonide Aldehydes and/or Ketones N/A N/A *Stereochemistry Considerations ⇒ - Reactions that only produce 1 asymmetric center with produce both R and S
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