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Procedure: Esterification and Infrared Spectroscopy

Submitted by crmckenzie on Wed, 04/11/2018 - 13:45

    Propanoic acid (0.973 mL, 13.0 mmol) and 3-methyl-1-butanol (1.194 mL, 11.0 mmol) were added at a 10 mL round bottom flask (RBF) along with 4 drops of sulfuric acid. The round bottom flask was attached to a reflux condenser with a distillation column pointing at a 45° angle. The mixture was refluxed for 15 minutes and the upper phase was then tipped back into the reaction flask. This was repeated twice more. The mixture was then removed from the heat and cooled for 15 minutes. The mixture was then pipetted into a centrifuge tube. The mixture was washed with water (1 X 1.00 mL). The mixture was then washed with sodium bicarbonate (2 mL, 2.6 mmol) twice. Lastly the mixture was washed with sodium chloride (1 mL, 3.69 mmol). The organic product was pipetted into a vial and ~20 CaCl2 spheres were added. The mixture sat for 5 minutes. The product (0.928 g, 58.51%) was then pipetted into a dry tared capped vial. Infrared spectroscopy was then performed.

 

Revised Background Section of Research Proposal

Submitted by benjaminburk on Wed, 04/11/2018 - 13:29

In this experiment we hope to find specific differences between physical attributes of the Campus Pond and nearby Puffers Pond. Campus Pond is a manmade pond, created in 1892, and is located in the center of the University of Massachusetts (UMass Amherst 1892). Meanwhile, Puffers Pond is the largest open body of water in Amherst, located about 3 miles from the center of town on conservation land (Amherst MA 2007). Because of the drastic differences in location and human interaction we believe that the results of this experiment will expose significant differences between the two bodies of water. The collected data will also lead to a better understanding as to why the the differences occur and how to handle potential problems that may be exposed as a result of these differences.

The techniques and procedure proposed in Rodrigo’s, Rojo’s and Armengol research article (2003), were used as a template for constructing the techniques used for physical characteristic testing in our procedure.

Facts / post lab answers

Submitted by michaelkim on Wed, 04/11/2018 - 10:28
  1. Equilibrium is driven towards product to produce a higher yield of ester in this experiment because the reflux step takes out everything else in the compound and keeps the organic layer itself. By doing reflux 3 times, total of 45 minutes, it gets rid of unnecessary substance in the compound other than the ester. So it is able to produce higher % than 70%.
  2. Using a sulfuric acid can speed up the reaction. Also, it can act as a dehydrating agent which is good for forcing the equilibrium to be higher yield of ester.
  3. Carboxylic acid is soluble in water. As it reacts with sodium bicarbonate it removes itself during the extraction phase. So, during extraction of the experiment, most of the excess carboxylic acid is removed.

Discussion afterwards of the experiment

Submitted by michaelkim on Wed, 04/11/2018 - 10:28

Discussion:

            In this lab, different esters were given to prepare before the lab even began. Given Isopentyl propionate, had to measure alcohol and carboxylic acid precisely that was calculated before the lab began. Then added sulfuric acids about 4 drops mixing them well. Distillation step then followed trapping the water with the help of sand bath to boil. As the vapors condensed and was ready to tip over, kept the lower water phase and got rid of the upper organic phase. For 45 minutes reflux was done. As it cooled down, water and sodium bicarbonate was added to remove the aqueous layer once again. Then calcium chloride was added then took the organic layer into the vial and put it in the capped vial. The ester at the end smelt fruity almost like a pineapple vodka. It was given for an IR spectrum test to prove how it is an ester and not something else. From the esterification IR spectrum graph, it can be proven as an ester since there is a huge curve around 2800-3000 which is only displayed by an ester. 1740-1750 is a carbonyl group that was displayed as an ester. The only thing on this graph that displayed failure was at around 3400 ish, which is where alcohol is displayed. This just means that some alcohol was displayed but it went below half way which means all the acid was gone. The % yield for the given ester was 70.13% which was high. 

Experimental Procedure for Esterification

Submitted by michaelkim on Wed, 04/11/2018 - 10:27

Use a 5-mL round bottom flask, measure alcohol and carboxylic acid precisely that was calculated in the prelab. Add sulfuric acid (4 drops) with caution and mix them using a clean pipet and expelling them back into the flask. Mixing well is required so it will not result in the concentrated sulfuric acid reacting to form unwanted darkly colored by-products. Add a few boiling chips and go through distillation. Trapping the water is more effective if the side arm points slightly downward when the round block flask with distillation head attached is held in an upright position in a 45-degree angle. Sand bath is then used to boil. Vapors should condense about 1/3 way up the reflux condenser. Overheating can make product and reactants to escape into the atmosphere. Two phases of liquid will collect in the side arm, upper organic phase and lower water phase. Remove water, after the reaction has refluxed for 15 minutes, raise the apparatus from heat and tip it back so that most of the upper phase in the side arm drips. Lower the apparatus back and using sand bath, resume refluxing for 15 minutes, then again lift and tip it back. Reflux for the 3rd and last time to make it 45 minutes total. Then cool it completely for 15 minutes. Take cooled content and use a pipet into a centrifuge containing water (1 mL). Mix well, lower layer to the top, remove the aqueous layer and place it into a beaker. Add sodium bicarbonate (1 mL), mix well, and remove the aqueous layer once again. Add 5 spheres of anhydrous calcium chloride to the liquid and swirl. Using a pipet, take organic layer into a vial and all the spheres should not clump together. Add more spheres if they are clumping together. Using a pipet transfer the liquid to a dry tared capped vial. Smell ester and check the odors of different esters made by classmates. Determine % yield of product, determine and interpret the IR spectrum. For comparison, check the IR spectra of a carboxylic acid, an alcohol, and an ester. 

ZENK Gene

Submitted by malberigi on Tue, 04/10/2018 - 22:45

When a bird hears a song, cells in the bird’s brain alter their biochemistry to alter gene expression and protein production that reshape cells in the learning center.  Allowing the bird to now do things it couldn’t before being exposed to the song.  One of the genes that contributes to these changes is ZENK which codes for a protein ZENK.  The ZENK protein is produced when a bird hears a song and is a transcription factor that regulates other genes influencing the way neurons interact with other neurons which can alter a bird’s behavior.

Draft 3

Submitted by cfellrath on Tue, 04/10/2018 - 22:15

In both the prokaryotic and eukaryotic cells glycolysis occurs in the cytoplasm of the cells. Although in the eukaryotic cell the formation of acetyl-CoA, the Citric Acid Cycle (Krebs) and the oxidative Phosphorylation occurs in an organelle called the Mitochondria. The opposite of breaking down glucose is gluconeogenesis, which forms glucose from pyruvate. In the prokaryotic cell the process of the formation of glucose occurs in the cytoplasm of the cell. In the eukaryotic cell gluconeogenesis starts in the mitochondria and finishes in the cytoplasm of the cell.

Draft 2

Submitted by cfellrath on Tue, 04/10/2018 - 22:07

The overall delta G of gluconeogenesis is negative. Although gluconeogenesis is considered an anabolic reaction because it is the building of a new structure, it is also a coupled reaction. Gluconeogenesis is couples with glycolysis therefore the energy given off by another reaction that is indirect such as the hydrolysis of ATP to ADP and Pi

Week 12 Draft 4

Submitted by jngomez on Tue, 04/10/2018 - 22:06

In Spring 2018, as part of the Writing in Biology course at the University of Massachusetts Amherst, each group designed a distinct proposal project examining a variety of factors. This experiment will examine Morrill buildings III and IV located in the University of Massachusetts, Amherst which are situated at opposite ends of each other. Arthropods thrive where there are plants or where the environment is warm. It is not well understood what other factors contribute to this notion. In this proposal, we aim to observe the distinct types of arthropods living or nonliving. In addition, factors that drive to the diversity of arthropods that are present on the Morrill Buildings III and IV window sills will be analyzed. Each group will be assigned a particular floor of either Morrill III or Morrill IV building. 

Draft 1

Submitted by cfellrath on Tue, 04/10/2018 - 21:59

Glycolysis is only “partial” in the oxidation of glucose because the reaction’s product is 2 pyruvate, 2 ATP, 2 NADH. Therefore the glucose is not fully oxidized of all its potential energy since much energy is stored with the two pyruvates. Pyruvate carried a decent amount of energy is the chain bonds of C-C and C-H. The fully oxidized product would be CO2 with no potential to reduce electron carriers.

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