Organic Chemistry CHM 252 and CHM 254L
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CHM 252 Organic Chemistry II
Spring 2001
Workshop #5

1. In the addition of HBr to 3,3-dimethyl-1-butene, the following results are observed:

  1. Explain why the different conditions give different product distributions.
  2. Write a detailed mechanism for each reaction that explains the origin of all products.

2. For each of the following reactions:

  1. Provide the structure of the product with the correct regiochemistry and stereochemistry.
  2. Indicate whether the regiochemistry is Markovnikov or anti-Markovnikov.
  3. Assign the stereochemical configuration at each stereocenter using the R/S and E/Z designations.
  4. Indicate whether the stereochemistry of addition is SYN or ANTI.
  5. Indicate whether or not intermediates are involved. If involved, are they carbocations or bridged?
  6. Identify the type of functional group produced in each case (e.g. alcohol, ether, aldehyde, etc.)

 

3. Tying Together Substitution, Elimination, and Addition Reaction through Synthesis

This part of the workshop involves the synthesis of ONE of the three different target molecules starting from the organic compounds and reagents listed in the SUPPLY TOOLBOX listed below. You can split up the group or all choose one to work on (your choice).  If you finish one, try a second or third. 

For each synthesis, you should provide the individual steps (see example) in the conversion as well as a complete description of the mechanism involved in each step (like we’ve done in class). NOTE: synthesis questions on exams will not involve mechanisms (we're doing this now just for further practice).  You might find it helpful to skim through Chapter 15 which introduces the concept of the multistep synthesis. Assume you can separate any mixtures of products that form during the course of a reaction.

Supply Toolbox

You are limited to using the following ORGANIC reagents: CH3CO2H, bromobenzene, CO2, benzyl bromide, ethanol, CH2Cl2, PPh3, p-toluenesulfonyl chloride, 1-chloro-1-methylcyclopentane, (R)-2-butanol, 1-propyne, methanol, pyridine, ethylene oxide, Hg(OAc)2, diethyl ether, THF, potassium t-butoxide, NaCN, mCPBA, sodium ethoxide, butyllithium, acetone, CHCl3, 1,3-butadiene, NBS, maleic anhydride, (trans)-2-methylcyclohexanol, cis-2-butene. You can assume all of the necessary inorganic reagents are available.

Synthetic Targets

 

NOTE: Be sure to look over the addition of HBr to the conjugated alkene template that is part of the handout from class.  There will be one question pertaining to it on the exam.  I want to see if you can apply your knowledge to solving this problem.   Refer to Fox and Whitesell pages 495-496.

 

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Timm A. Knoerzer
email
Naz Chem. Dept.
Naz. Home Page

Last Updated Thursday, February 15, 2001 06:13:25 PM