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Organic Chemistry Lab II

by: Corbin Crist DDS

Organic Chemistry Lab II CHEM 3780

Marketplace > Western Michigan University > Chemistry > CHEM 3780 > Organic Chemistry Lab II
Corbin Crist DDS
GPA 3.81

Elke Schoffers

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Elke Schoffers
Class Notes
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This 1 page Class Notes was uploaded by Corbin Crist DDS on Wednesday September 30, 2015. The Class Notes belongs to CHEM 3780 at Western Michigan University taught by Elke Schoffers in Fall. Since its upload, it has received 25 views. For similar materials see /class/216968/chem-3780-western-michigan-university in Chemistry at Western Michigan University.


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Date Created: 09/30/15
CHEM 3780 REAC 716 Nitrating Acetanilide Electrophilic Aromatic Substitution February 814 2008 WW 0 039 T H H IL CH N T NYCHS vi CHa O T 3 HNOS H2804 N CH3 or O or or O T 0 Y N 5 O W H oquot o O mp94C mp1550 mp214 217C Experimental Notes Please read and be familiar with the background p 163166 and procedure p 166169 before coming to lab You will do only the nitration of acetanilide It is important to heed the warning in Note 2 p 168 You will determine the regiochemistry of the nitro group addition by melting point comparison A 1H NMR of the product will also be provided Pre Lab Preparation 1 2 W ma What precautions will you take a when handling the concentrated acids used in this experiment and b when adding the sulfuric acid solution to the nitric acid solution Why is it important to add the nitrating solution slowly to your acetanilide De ne the following terms as they pertain to this experiment and know of speci c examples Electrophile Regioisomers Activating group Deactivating group Arenium ion Give the general mechanism for electrophilic aromatic substitution Arenium ions a Is the acetamide group activating or deactivating b Will the acetamide group most likely direct the nitro group ortho meta or para How could you use 1H NMR to distinguish your nitroacetanilide from all of the possible nitration products Review the handout on coupling constantsiespecially the part on p 1 which discussed the 1H NMR for disubstituted aromatic rings De0579 75 pts Lab Write up 1pts Date and Title of Experiment 1 pts 5 pts Objective Reaction Scheme with balanced equation Show the reaction of acetanilide with the nitrating agent NO 139 when the attack is meta include the arenium ion intermediate and its resonance structures ii when the attack is para include the arenium ion intermediate and its resonance structures 4 pts Table of physical constants for each reactant and product Include hazards associated with use of each 4 pts Outline of procedure 25 pts Observations and calculations data recorded during the lab 15 pts Include observations that you make during the experiment 2 10 pts Show the calculation of the theoretical yield and percent yield of your nitration product 3 Obtain NMR spectra from the TA and determine the melting point before and after recrystallization see Section 4 on page 168 25 pts Results and Discussion 1 10 pts Based on the observed melting point before and after recrystallization what would you conclude was the structure of the product 2 10 pts Label and assign the peaks of your 1H NMR spectra provided of acetanilide and nitroacetanilide Prepare a table in your laboratory notebook to report this data 3 5 pts 246trinitrotoluene TNT is synthesized by trinitrating toluene The rst nitration proceeds much faster than the second two Brie y explain What is the structure of TNT 10 pts Conclusions What two new things did vou learn while doing this lab


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