Preparation and SN1 Reactivity of 2-Bromobutane

Table of contents

Introduction

The overall goal of this experiment is to understand and be familiar with SN1 reactivity. We also learned how to prepare 2-Bromobutane by learning how to distill and extract this product from its organic layer. Finally, another goal was to specifically understand the relative reactivity of alkyl halides under SN1 conditions by reacting the alkyl halide and silver nitrate in ethanol.

Results and Discussion

The Overall Reaction

The proposed mechanism experimental procedure to prepare the 2-Bromobutane you must fill a 100 mL round bottom flask with 20 mL of 12M sulfuric acid and 7. 4 mL of 2-butanol. Then add 8. 0 g of ammonium bromide along with a magnetic stir bar. Then attach the flask to the apparatus, which is mounted on a Thermowell over a stirrer and a condenser attached to it, along with the thermometer in the flask. Then the mixture was heated at 90oC then kept at the range of 90oC-100oC for 30 minutes.

When that is completed add 20 mL of water into the flask to perform a simple distillation to collect the distillate in a graduated cylinder, keep doing this until there is no more 2-Bromobutane collected. Use a Pasteur pipette to draw off the organic layer to another container. Add the potassium carbonate to allow the liquid to dry by swirling it. Once this is completed the reactivity of alkyl halides under SN1 conditions was tested. Adding two drops of our product and the other different compounds into different test tubes along with 1mL of ethanolic silver nitrate reagent.

We are comparing these by seeing how they react and if there is no reaction after 5 minutes we will place the test tubes in a beaker of water that is heated at a temperature of 70oC-80oC and observe what happens.

Experimental Stoichiometry

Compound Molecular Weight Quantity Moles
2-Butanol 74. 122 g/mol 7. 41 mL (6. 01 g) 0. 081
Sulfuric Acid 98. 079 g/mol 20. 1 mL 0. 242
Ammonium Bromide 97. 94 g/mol 8. 02 g 0. 082

The limiting reagent is the 2-Butanol.

Yield Data

Product Name 2-Bromobutane
Molecular Weight 137. 02 g/mol
Boiling Point Range 89°C-91°C
Theoretical Yield (Moles) 0. 081 moles
Theoretical Yield (grams) 11. 09 grams
Actual Yield (grams) 6. 84 grams
Actual Yield (moles) 0. 05 moles
Percent Yield 62%

NMR Table Signal

* Chemical Shift (ppm) Multiplicity Integration
A 4. 1 ppm Sextet 1
B 1. 85 ppm Pentet 2
C 1. 7 ppm Doublet 3
D 1. 05 ppm Triplet 3

Reactivity of Alkyl Halides

Compound Room Temperature Heating
1-Bromobutane After 30 seconds, the mixture was a cloudy whitish color but no precipitate formed After 5 minutes, it changed into a yellow color with precipitate formed.
2-Bromobutane After 30 seconds, the mixture was a light yellowish color and a precipitate formed instantly. Not Heated
2-Bromo-2-methylpropane After 30 seconds, the mixture was yellow and a precipitate formed instantly. Not Heated
Compound Room Temperature Heating
1-Chlorobutane After 30 seconds, the mixture was clear. After 5 minutes, the color changed slightly to white and lightly cloudy.
2-Bromobutane After 30 seconds, the mixture was a white cloudy color and formed a precipitate instantly. Not Heated
2-Iodobutane After 30 seconds, the mixture was yellow and precipitated instantly. Not Heated

Conclusion

In conclusion, the SN1 reaction of 2-Bromobutane was performed. According to the Yield Data table, when the actual yield and theoretical yield are calculated we can get the percent yield, which was 62%. At least this number was higher than 50%; I can understand how this could have happened. When I was drying the reagent with potassium carbonate, prior to that I had put the other pellets, which were calcium chloride on accident.

This probably affected my percent yield also with the fact that the temperature was not well maintained it kept fluctuating under 90OC. According to the reactivity of alkyl halides, the results of these tables can conclude the theories of the conditions of SN1 reactions. The first table states that the tertiary carbocation is more stable which allows this reaction to perform faster than second and primary structured carbocations. Then the second table can conclude that iodine is the best leaving group because it is a much weaker base than the bromide ion and chloride ion causing it to react faster.

Calculate the price
Make an order in advance and get the best price
Pages (550 words)
$0.00
*Price with a welcome 15% discount applied.
Pro tip: If you want to save more money and pay the lowest price, you need to set a more extended deadline.
We know how difficult it is to be a student these days. That's why our prices are one of the most affordable on the market, and there are no hidden fees.

Instead, we offer bonuses, discounts, and free services to make your experience outstanding.
How it works
Receive a 100% original paper that will pass Turnitin from a top essay writing service
step 1
Upload your instructions
Fill out the order form and provide paper details. You can even attach screenshots or add additional instructions later. If something is not clear or missing, the writer will contact you for clarification.
Pro service tips
How to get the most out of your experience with MyStudyWriters
One writer throughout the entire course
If you like the writer, you can hire them again. Just copy & paste their ID on the order form ("Preferred Writer's ID" field). This way, your vocabulary will be uniform, and the writer will be aware of your needs.
The same paper from different writers
You can order essay or any other work from two different writers to choose the best one or give another version to a friend. This can be done through the add-on "Same paper from another writer."
Copy of sources used by the writer
Our college essay writers work with ScienceDirect and other databases. They can send you articles or materials used in PDF or through screenshots. Just tick the "Copy of sources" field on the order form.
Testimonials
See why 20k+ students have chosen us as their sole writing assistance provider
Check out the latest reviews and opinions submitted by real customers worldwide and make an informed decision.
Business and administrative studies
Excellent work ,always done early
Customer 452773, February 21st, 2023
Nursing
thank you so much
Customer 452749, June 10th, 2021
Philosophy
Thank you
Customer 452811, February 17th, 2024
English 101
great summery in terms of the time given. it lacks a bit of clarity but otherwise perfect.
Customer 452747, June 9th, 2021
Business and administrative studies
always perfect work and always completed early
Customer 452773, February 21st, 2023
10th grade English
very good
Customer 452773, March 26th, 2023
Human Resources Management (HRM)
excellent job
Customer 452773, June 25th, 2023
Business and administrative studies
Excellent job
Customer 452773, March 17th, 2023
Psychology
Thank you!
Customer 452545, February 6th, 2021
History
Don't really see any of sources I provided, but elsewise its great, thank you!
Customer 452697, May 8th, 2021
Business and administrative studies
great job as always
Customer 452773, February 26th, 2023
Sociology
THANK YOUUUUU
Customer 452591, March 18th, 2021
11,595
Customer reviews in total
96%
Current satisfaction rate
3 pages
Average paper length
37%
Customers referred by a friend
OUR GIFT TO YOU
15% OFF your first order
Use a coupon FIRST15 and enjoy expert help with any task at the most affordable price.
Claim my 15% OFF Order in Chat
Close

Sometimes it is hard to do all the work on your own

Let us help you get a good grade on your paper. Get professional help and free up your time for more important courses. Let us handle your;

  • Dissertations and Thesis
  • Essays
  • All Assignments

  • Research papers
  • Terms Papers
  • Online Classes
Live ChatWhatsApp