Answers to the synthesis problems are given below. These answers have been selected as they are short but there are probably other reasonable / alternative solutions ..... Of course they are based on the reactions covered in the Fall semester ! 

Common errrors:

• Using the wrong reagents e.g. base to eliminate alcohols or acids to eliminate halides, or HX to radically halogenate alkanes.
• Not showing how to prepare CH₃CH₂SH or CH₃CH₂Br (depending to the route used) in B since the question asked and not starting the syntheses from hydrocarbons as specifically asked for in the question.
• In C using several steps where one would work, not forcing SN1 to get the C+ rearrangement.
• In D, not paying attention to the stereochemistry of the product or of the reaction steps. SN1 will lead to the racemized product and SN2 inversion, so we need a double inversion, i.e. two reactions that each cause inversion. Using alcohol to tosylate to chloride will give the opposite stereochemistry to that required because the tosylate has the same stereochemistry as the original alcohol.
  

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