EXPERIMENT 2

COURSE : SKO 3033 (ORGANIC CHEMISTRY 2) GROUP : B LECTURERS NAME : EN. MOHAMAD SYAHRIZAL BIN AHMAD STUDENTS NAME AND ID :

NAME NURUL HANA BALQIS BT BAHAROM NAPSIAH BINTI ABDUL RAHMAN

ID D20101037312 D20101037298

OBJECTIVES OF EXPERIMENT: 1. To synthesis tert-butyl chlorides from tert-butyl alcohol.

RESULTS: 1. Mass of tert-buty alcohol: 7.819 g Density =

Mass = volume x density Mass = x

= 7.819 g 2. Mass of tert-butyl chloride = 0.0 g 3. Theoritical mass of tert-butyl chloride = 11.09 g

No. of mol= mass

molar mass 74 g/mol

Mol of tert-butyl alcohol = 7.819 g = 0.12 mol

1 mol tert-butyl alcohol = 1 mol tert-butyl chloride 0.12 mol ter-butyl alcohol = 012 mol tert-butyl chloride Mass of tert-butyl chloride = 0.12 mol x 92.45 g/ mol = 11.09 g 4. Percentage of yield = 0 %
Percentage yield = x 100%

= =0% 5. Boiling point = 51.0

x 100%

DISCUSSION: 1. From the experiment we dont get the value of percentage yield. This is because we

dont get the product, which is tert-butyl chloride during the distillation process. The experiment is not succeed. 2. Therefore, there were many error occurred during conduct this experiment. The first

error is, during using the separatory funnel. As we know, before separate the solution, we should wait until the layered of two solutions are clearly separated. But, we dont wait for a long time. So, maybe the solutions in the separatory funnel is still mixed. Other than that, during allow the acid layer to drain into flask, we cant see the layer clearly. So that, the remaining solution that contain tert-butyl chloride is accidentally drain with the acid. 3. Beside that, we also use the big round bottom flask, which is 250 mL during the

distillation. The size of round bottom flask that we used is not suitable to the volume of solution that we got from the separation of solution using separatory funnel. The volume that we got is too small compare to the volume of round bottom flask. So that, the steam of tertbutyl chloride released when it achieve the boiling point, will stick to the surface of round bottom flask. So that, no product in the erlenmayer flask. 4. Beside that the position of condenser is not incline enough to let the product flowing.

Therefore, the product stuck in the condenser tube. 5 Based on theory, the alkyl halide(tert-butyl chloride) was synthesized by Sn1 reaction

from alcohol(tert-butyl alcohol). However, the hydroxide ion is not a particularly good leaving group. On the other hand, if one additional hydrogen atom is added, the leaving group becomes water, which is very stable and therefore easier to form. The mechanism for the reaction is show when answering the question.

QUESTION: 1. Write the complete mechanism of the reaction.

2. Primary and secondary halides are not synthesized using this method. Explain why? Primary and secondary halides are not synthesized using this method because this procedure is much slower, and the formation of the primary alcohols usually requires prolonged heating.

3. Why the percentage of the yield in this experiment is less than 100%. If our experiment is succeed and we got the product, I am sure that the percentage of the yield will be less than 100%. This is because, some of the tert-butyl chloride is lost on the flask or the tert-butyl chloride was perhaps to elimination.

4. What is the function of dehydrate CaCl . The function is to remove dissolved water in the erlenmayer flask.

Conclusion: The tertiary alkyl halide is synthesis by Sn1 reaction from tertiary alcohol and HCl. The experiment is not succeed because we do not get the product of tert-butyl chloride by the distillation process due to errors during conduct the experiment.