Report for Synthesis of "1-Bromobutane"

1.  Balanced equation for reaction as you carried it out.

2.  Step-wise mechanism for the reaction.  Use curved arrow formalism and label the RDS. Show how each product is formed if more than one product is possible.   Use additional paper if necessary.  Give the name of the mechanism.

3.  weight of the starting alcohol:

   moles of alcohol:

   weight of the product halide:

   moles of product:

   % yield:

  literature values for the bp of the 

   expected product(s):

4.  Discussion of results.

5. Answer the following questions.

a) Why did you wash the crude product with NaHCO₃?

b) Why did you then wash it with water?

c) Why was the 1-bromobutane treated with anhydrous calcium chloride?

 

d) Was the product produced by an Sn1 or an Sn2 mechanism?  How could you verify this?

e) What role did the sulfuric acid play in this experiment?  Explain! equations!

6.  Attach the carbons from your notebook and table of physical properties.

Report for Synthesis of "2-Chloro-2-methylbutane"

1.  Balanced equation for reaction as you carried it out:

2.  Step-wise mechanism for the reaction.  Use curved arrow formalism and label the RDS. Name the mechanism! Show how each product is formed if more than one product is possible. Use additional paper if necessary.

3.  weight of the starting alcohol:

    moles of alcohol:

    weight of the product halide:

    moles of product:

    % yield:

    literature values for the bp of the 

    expected product:

4.  Discussion of results.  Be sure to compare the synthesis of 1-bromobutane with that of 2-chloro-2-methylbutane.

5. Include a table showing the following for the syntheses of n-butyl bromide and for tert-butyl choloride:

          time of reaction

          temperature of reaction

          catalyst

          %yield

         class of alcohol

          mechanism

5. Answer the following questions.

a) Draw all of the isomeric butanols.

b) Why did you wash the crude product in this experiment with aqueous sodium bicarbonate?

c) Why were you able to wash the crude 1-bromobutane with saturated NaHCO₃ while 5% NaHCO₃ was used in the washing of 2-chloro-2-methylbutane?

d) What is one major disadvantage of washing with sodium bicarbonate?

e) Neopentyl alcohol reacts with conc. HCl to produce tert-pentyl chloride.  Outline all steps in the mechanism to show how this product is formed.

f) Why does 1-pentanol produce only 1-bromopentane and not 2-bromopentane when reacted with HBr?

g) Solid sodium hydroxide is a drying agent.  Why did we not use it in place of calcium chloride when drying the crude product?

Attach the carbons from your notebook and table of physical properties.

© Dr. Noel Sturm 2009