Organic 1 discussion 6 | Chemistry homework help



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Substitution vs. Elimination
Read the instructions carefully and answer the following questions in the space provided. Then
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1. Compare and contrast SN1, SN2, E1 and E2 reactions. What are some obvious similarities
and differences between each reaction pathway? What are the requirements for each
reaction to work? Discuss why SN2 is in direct competition with E2 while SN1 is in direct
competition with the E1 reaction pathway. What is the rate expression for each? Which
reactions are concerted? Which reactions are step-wise? Which reactions are
stereospecific and what is the stereospecificity of each that are? How do the variables
below help influence which reaction pathway will lead to the major product formed?

a. Substrate (substitution pattern and leaving group ability)
b. Nucleophile/base strength (weak or strong) and size (unhindered or hindered)
c. Solvent (polar-aprotic or polar-protic)
d. Temperature (low/ambient temps vs. higher temps)


2. Below (on the next page) are 4 reactions. For each, indicate what reaction pathway lead to
each major product shown. Discuss the factors that led you to each decision. Use each
pathway (SN1, SN2, E1, and E2) only one time. Where there any reactions where you had
a more difficult time deciding versus others? Draw an arrow-pushing mechanism for each
reaction to clearly show the electron movement which led to each major product shown.


3. Consider the reaction scheme shown below.

Discuss two independent experiments you could do in a typical undergraduate lab to
experimentally determine which type of substitution reaction took place. Be specific and briefly
explain how each experiment would be able to provide you with the information necessary to
determine this. In other words, what outcomes do you expect from your experimental design. The
experiments could also include an instrumental technique. Your answer should not be something
along the lines of simply saying to “check (R) and (S)”. Each experiment should have at least two
parallel reactions that you are describing. Make sure to include any instrumentation you would
need to analyze products in order to decide which substitution product is taking place and what the
analysis would be expected to tell you.

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