CHEM 2311L/2411L Lab Report Cover Sheet

Name: _________________________ TA: Doug Jackson/ Matt McKinley/ Tom Irvin

Date: _________________________

Experiment: _____________________________________________________

Pre-lab (25 points) Title Introduction Table of Reagents Safety Information In-lab (20 points) Procedure/Data/Obs. Data Sheet Quality Data/Spectra Recorded

____________ ____________ ____________ ____________

(2 points) (13 points) (5 points) (5 points)

____________ ____________ ____________

(5 points) (5 points) (10 points)

Post-lab (50 points) Results/Spectra, Discussion ____________ and Conclusions Calculations ____________ Answers to Questions ____________ Discretionary Points (5 points) Total ____________` ____________

(35 points) (10 points) (5 points) (5 points) (100 points)

TA Comments:

Dehydration of Alcohols Introduction One important way to form alkenes in organic synthesis is by dehydration of an alcohol precursor. The dehydration reaction proceeds under thermal conditions in refluxing acid through a carbocation intermediate.

The thermal conditions for this reaction are high temperature and a long reaction time. Under these conditions, if multiple products are possible, then the more stable product should be the major product and predominate. The more stable product is known as the Zaitsev Product.

It is not known to what degree the Zaitsev Product will predominate in the reaction. In other words, it is not able to predict what the product percentage will be in the final product of a reaction. The goal of this experiment is to dehydrate 3-methyl-3-pentanol to form alkene products in some unknown ratio. Proton nuclear magnetic resonance spectroscopy will be used to determine the ratio by looking at the relative proton integration. Using the

integrated spectra of the product mixture, the product distribution (% of each product) will be determined for the final sample. NMR instruments rely on large magnetic fields to align nuclear spins in a way to make them detectable to a probe. Every proton of a compound in a different chemical environment gives a different H NMR signal because every position in a compound experiences a shielding effect due to its electron cloud. The chemical shift of the spectrum is affected by several things, the close a proton is to an electron withdrawing atom, the greater the shift, the proximity to a double bond or aromatic ring.

Table of Reagents Name 3-methyl-3pentanol Structure Molecular Weight 102.174 g/mol Boiling Point 122.4 C Melting Point -23.6 C

Phosphoric Acid

98 g/mol

158 C

42.35 C

Safety Always lab goggles during the experiment. Remember to never heat a sealed apparatus. Phosphoric acid is corrosive, so in addition to goggles, gloves are required. The starting material and products of the experiment are flammable so avoid any sources of ignition.

Sarah Merkel Experiment 6 Lab Partners: Meg Adams and Jesse Cann Lab Performed on October 2nd, 2012

Data and Calculations Amount of 3-methyl-3-pentanol added Amount of Phosphoric Acid Mass of collection vial Mass of collection vial + sample Mass of Sample 2.01 grams 0.25 mL 1.832 grams 3.028 grams 1.196 grams

% Of original recovered = Shift 6.5 ppm 5.9 ppm Integration 12 mm 4 mm

Ratio of Integration = Ratio of Hydrogens = % Distribution of 3-methyl-2-pentene = % Distribution of 2-ethyl-1-butene = Mechanism of Dehydration of Alcohol

Discussion From the proposed mechanism above, the dehydration of the 3-methyl-3-pentanol will produce two different products. From the Zaitsevs Rule, the most stable product will predominate. The most stable product according to the Zaitsevs Rule is the one that is typically the most substituted one. The percent of original recovered in this experiment is 59.5 %. This Experiment produces two different products, 3-methyl-2-pentene and 2-ethyl-1-butene and also gives off a water molecule and a phosphoric acid. From the NMR spectrum, a H2O impurity is found in the region around 4.5 ppm. The existence of this peak proves that a small water impurity is present in the final sample. To determine the product distribution in the final sample, an HNMR spectrum was taken. From the spectrum, the ratio of integration can be determined. In the spectrum taken, the ratio of integration is 3:1. One product contains 2 hydrogens, while the other product only contains 1 hydrogen. To account for the difference in protons, the integration number for the product that only contains 1 hydrogen is multiplied by 2. The number integration ratio is 3:2. To determine the product distribution of the product with the integration value of 3, a simple calculation of 3/5 leads to the percent distribution of 60%. To determine the product distribution of the product with the integration value of 2, a simple calculation of 2/5 leads to the percent distribution of 40%. The final step in the NMR analysis is to determine which peak belongs to which product. This analysis is done by looking at the multiplicity splitting of the peaks. The peak located at 6.5 ppm has what appears to be a quartet. The peak located at 5.9 ppm has what appears to be a singlet. From this information, it is determined that the peak

located at 6.5 ppm belongs to 3-methyl-2-pentene due to hydrogen being split into a quartet by 3 hydrogens. The peak located at 5.9 ppm belongs to 2-ethyl-1-butene because of the 2 hydrogens that are not split by neighboring hydrogens. Now that the peaks have been labeled, it is evident that the 3-methyl-2-pentene is the major product and is 60% of the product of the dehydration of the alcohol. The 2ethyl-1-butene is the minor product and is 40% of the product of the dehydration of the alcohol. These findings agree with Zaitsevs Rule because the major product is the one that is the most substituted and the minor product is less substituted. Post-Lab Questions 1. The proposed product distribution does agree with Zaitsevs rule. The product found 60%