CHE 311 "1-Bromobutane"

Your lab report should follow the format and consist of the following:

Title (be specific)

Your Name

Date

Section Number (CHE 311-0X)

1. Introduction:

• Purpose of Experiment
• Important theory and/or background material
• Structures and/or reactions
• Approproate references to literature (if necessary).

Balanced equation for reaction as you carried it out.

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.

2. Methods / Materials: Usually a simple list, but make sure it is accurate and complete.

3. Experimental Procedure:

• Describes the process in chronological order
• Explain all of the steps in the order they actually happened, NOT as they were supposed to happen.
• If you've done it correctly, another researcher should be able to duplicate your experiment.
  

4. Results and Discussion:

• Results are usually dominated by calculations, tables and figures; however, you still need to state all significant results explicitly in verbal form.
• Discussion focuses on a question of understanding, "what is the significance or meaning of the results?".

weight of the starting alcohol:

moles of alcohol:

weight of the product halide:

moles of product:

% yield:

5. References and Post-Lab Questions:

literature values for the bp of the

expected product(s) :

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!

Synthesis of "2-Chloro-2-methylbutane"

1. Introduction:

• Purpose of Experiment
• Important theory and/or background material
• Structures and/or reactions
• Approproate references to literature (if necessary).

Balanced equation for reaction as you carried it out.

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.

2. Methods / Materials: Usually a simple list, but make sure it is accurate and complete.

3. Experimental Procedure:

• Describes the process in chronological order
• Explain all of the steps in the order they actually happened, NOT as they were supposed to happen.
• If you've done it correctly, another researcher should be able to duplicate your experiment.
  

4. Results and Discussion:

• Results are usually dominated by calculations, tables and figures; however, you still need to state all significant results explicitly in verbal form.
• Discussion focuses on a question of understanding, "what is the significance or meaning of the results?".

weight of the starting alcohol:

moles of alcohol:

weight of the product halide:

moles of product:

% yield:

5. References and Post-Lab Questions:

literature values for the bp of the

expected product:

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

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

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?

© Dr. Noel Sturm 2014