How much of each reactant did you start with (alcohol and HCl)?


reactant did you start with (alcohol and HCl)
No additional discussion questions. Your results and discussion should follow the format of Part
V in the “Laboratory Notebook Experiment Entries” section from your laboratory introductory
materials. Below is a guide that may help you when preparing your results and discussion:
V. Results & Discussion
A. Present data obtained from the experiment in an orderly manner (tables, graphs, etc)
whenever possible.
 How much of each reactant did you start with (alcohol and HCl)?
 How much alkyl halide did you end with?
 What was your theoretical yield and % yield?
 What were the results of your sodium iodide and silver nitrate tests?
 Was the IR able to identify your product? If so, to what compound?
B. Show all calculations (don’t forget % yield or % error where appropriate).
% 𝑦𝑖𝑒𝑙𝑑 =
𝑒𝑥𝑝𝑒𝑟𝑖𝑚𝑒𝑛𝑡𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
× 100 % 𝑒𝑟𝑟𝑜𝑟 =
|𝑡𝑟𝑢𝑒 𝑣𝑎𝑙𝑢𝑒−𝑒𝑥𝑝𝑒𝑟𝑖𝑚𝑒𝑛𝑡𝑎𝑙 𝑣𝑎𝑙𝑢𝑒|
𝑡𝑟𝑢𝑒 𝑣𝑎𝑙𝑢𝑒
× 100
 This experiment is a synthesis, so how will you calculate the theoretical yield of
t-butyl chloride? Hint…requires stoichiometry. You will have to determine whether
the alcohol or acid is the limiting reagent as well.
 What was the IR software’s calculation for the “match”? (100 is a perfect match
C. Discuss all data obtained and the information which was gained from it.
 What do you think of your yield?
 Are your results from the sodium iodide and silver nitrate tests what you expected?
 What do you think of your IR match?
 What peak(s) appeared or disappeared in the IR spectrum to indicate loss of
reactant/formation of product?
D. Discuss experimental errors and possible sources of error, and how these errors affect
your results.
 Were there steps of the protocol that you messed up (not keeping things chilled, not
mixing for long enough time, discarding the wrong layer(s), poor separation, failing
to neutralize your reagents, etc.)
 What could have caused loss of yield?
 What possible by-product(s) could you have produced? Did you observe gas
 What could have caused possible false negative or false positive sodium iodide or
silver nitrate test results?
 What could have made it difficult for the IR software to properly match your product
to its library?
 Can you see any obvious peaks in the IR that indicate a contaminant and what
functional group(s) it may have?

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