tut9 - This reaction is, however, ineffective for...

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1 CHM 138H TUTORIAL 9 As described in the course outline, the tutorial quizzes will be based closely upon the textbook questions recommended below for this week's tutorial as well as those recommended in last week's tutorial. You should be able to do the questions below from the course textbook (J. McMurry, 7 th Edition): Chapter 10: 10.8-10.10, 10.13, 10.15, 10.17-10.18, 10.30, 10.36-10.37, 10.40-10.42. Of the above, the following represent some of the better questions: 10.30, 10.36-10.37, 10.40-10.42. In addition, the following problems will be discussed, which focus on Chapter 10 material and concepts discussed in lecture: 1. One way to prepare a tertiary alkyl chloride or bromide is to react a tertiary alcohol with HX (X = Cl or Br) in an inert solvent.
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Unformatted text preview: This reaction is, however, ineffective for preparation of primary alkyl halides. Discuss the reason behind this, with reference to the operative reaction mechanism and using curved arrows to represent electron flow. How might a primary alkyl chloride be prepared from a primary alcohol? 2. Grignard reagents (R-MgX) are exceptionally useful in organic synthesis, as seen in detail in Chapter 17. They do have limitations, however. Explain, with the use of a reaction mechanism (including curved arrows) why a Grignard reagent (e.g. ethylmagnesium bromide) is unstable in an alcohol solvent such as ethanol. Why cant Grignard reagents generally be prepared from alkyl fluorides? OH HCl ether Cl...
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