Stereochemistry: Addition of Bromine to Trans-Cinnamic Acid Article


Needed Prelab Blood pressure measurements: McMurry Part 5, Portions 8. a couple of & twenty one. 2

Morhig, Sections several. 1 and 7. a few.

Previous methods that you must know and be able to conduct: Suction Purification and Burning Point

This kind of experiment is made to demonstrate two concepts. First, it will supply a demonstration of how chemists are able to use chemical reactions to comprehend reaction components. Second, is the concept of multi-step synthesis. You'll certainly be performing this reaction:

Isomer IIsomer II

+ Enantiomer+ Enantiomer

Brominetrans-Cinnamic Acid2, 3-Dibromo-3-phenylpropanoic acid MW 160 g/molMW 148 g/molMW 308 g/mol

bp 70 °Cmp 133-134 °Cmp 93-95 °Cmp 202-204 °C

When an electrophile, such as bromine, adds to an alkene, the addition can be done in a syn trend, in which the two groups improve the same aspect of the molecule, or in an anti fashion, in which the teams add to opposing sides of the molecule. With regards to the mode of addition, vision or anti, and the stereochemistry of the beginning alkene, numerous stereoisomers is going to result. Occasionally, a racemic mixture of goods is formed, other times a meso compound can be produced.

The Fischer projections shown over are two possible stereoisomers that could form in the bromination reaction you will perform. One is the result of a syn addition, the different is the consequence of an anti addition setting. Note that each would form as a racemic mixture, (+). You in order to determine, based on the melting point of the product, which pair of enantiomers is made. By being aware of which enantiomeric pair is created one can forecast a possible mechanism. Tip: you can foresee the stereochemical outcome of any syn or anti addition of bromine to alkenes before you step ft . into the lab.

The simplest sort of a multi-step synthesis is to examine just about any commercial treatments. Almost without exception that medicine was prepared by a series of reactions instead of in a single stage. A multi-step synthesis generally requires a chemist to perform a chemical reaction, isolate, purify and characterize the product and then employ that product as the starting materials for the next response. You will be using the product with this reaction otherwise you starting material next week. Will probably be important for you to have the product from this week properly identified so you can correctly predict the merchandise of subsequent week's effect.

➢ The most time consuming part of this experiment is to create a the glasses. Be sure almost all fittings happen to be tight, well-greased, and clamped so as to prevent any escape of bromine vapors into the laboratory environment. An actual system is presented to you in the lab that you can look at.

➢ You will need to set up the apparatus as shown in physique 7. four a on-page 63 of Mohrig.

NOTICE: You are responsible for calculating the amount of trans-cinnamic acid (in grams) equivalent to 4 mmol. You'll want this performed before you enter the laboratory.


Molecular bromine is quite toxic and corrosive; the vapors happen to be damaging towards the skin eye and respiratory tract. Wear safety gloves and DO NOT EVER ARE YOU TO GET RID OF THE BROMINE STOCK OPTION FROM THE COVER. Only remove your bromine solution in the stoppered channel. Sodium thiosulfate reduces Br2 to Br-1. When working with Br2, always keep a bottle of 5% sodium thiosulfate handy for rinsing the skin in the case of contact.


➢ Assemble a 50 cubic centimeters round-bottom flask with a Claisen head, reflux condenser, and addition channel. Into the round-bottom flask, add trans-cinnamic chemical p (4 mmol) and 12 mL of methylene chloride. Add a mix bar.

➢ Attain 4. zero mL of the 1 . 0 M solution of bromine in methylene chloride inside the addition direct. Attach a heating layer and variac and temperature the blend to a soft reflux. The variac environment should primarily be 25-30. Adjust this kind of setting as necessary until the remedy is refluxing....

Chickamauga. This kind of essay is around Ambrose Bierce’s dark short story, «Chickamauga. »