Chem 203 Fall 2016 Chem 203 Name______________________________________________Section:______TA:_______________________ LA Problem Set 5 Must be completed and signed by a LA or Dr. B. by no later than October 14th to obtain a signature to receive homework credit for this problem set 1. Definitions: It is important that you understand the definition of terms so that when we use them in class you can associate them with examples. a. Reaction-? b. Mechanism-? c. Elementary Step-? d. Formal Charge (as it applies to Lewis Structures)-? e. Formal Charge = valence electrons -? f. Proton Transfer: what are the types? g. Nucleophilic Addition-? h. Nucleophilic Elimination-? 2. Create a diagram or concept map that illustrates how the concepts in Question 1 are connected to one another. Make sure you label the connecting points so that you make it very clear why you have chosen to connect these concepts in the way that you do in the diagram. Here are two examples to provide you with ideas: 1 Chem 203 Fall 2016 3. In the reaction below label the nucleophile, electrophile, and leaving goup as well as the name of the elementary steps for each part of the reaction mechanism. You will also need to write in the arrows and the products in step 3 of the mechanism. In a sentence descibe how you decided upon the final products and where to place the 2 Chem 203 Fall 2016 arrows in this step. O O O step 1 H step 2 O
OH O + O O + step 3 ? OH 4. Using the names of the following elementary steps Proton Transfer (under acidic, neutral or basic conditions, within the molecule, or between molecules) Nucleophilic Addition, Nucleophilic Elimination name each step with the appropriate elementary step name, draw in the arrows to indicate the movement of the electrons in each elementary step, and label the site that is electron rich and electron deficient. Make sure you include all formal charges and all lone pairs. O O O O
H H H + H O H OH H H
O O O
NH3 NH3 O O
OH NH2 OH NH2 3 Chem 203 Fall 2016 H H O O O
O H H O O H H O Cl O
O O O O H O H H
H O O H H Cl H H+ O H
O O 4 Chem 203 Fall 2016 5. Complete the reactions below and draw in the arrows and the lone charges for all reactants. O
+ Cl N Nucleophilic Addition
+ CH3OH O
OH H 2SO 4 + CH3 Protonation
+ OCH3 Protonation
O O O
Nucleophilic Elimination 5 Chem 203 Fall 2016 O H
N + Cl Nucleophilic Addition
+ CH3OH O
OH H 2SO 4 + Proton Transfer CH3 O
OCH3 + Proton Transfer
Nucleophilic Elimination O
H 3C O + O H 3C O H
H Proton Transfer
H Proton Transfer 6 Chem 203 Fall 2016 6. Flow chart the isolation and purification of phenyl acetic acid from the reaction below. Could you follow this reaction by TLC? How would you prepare the samples for TLC analysis? O
CH O O
OH 3 equivalents NaOH
Reflux for an hour 2
phenyl acetic acid,
slightly water soluble
Mp 77 0C O HO O
reaction goes 100% to
miscible in water
Mp 17 0C 7
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