Exam 1 Flashcards
Provide the structure for the following molecule:
para-nitrobenzoic acid
Please draw the π molecular orbital diagrams of both 1,3-butadiene and ethylene (CH2=CH2). Fill in each diagram with the appropriate number of electrons. Clearly label the highest-occupied (HOMO) and lowest unoccupied (LUMO) molecular orbitals of each. Draw a dotted line between the orbitals that interact in a Diels-Alder reaction (assume normal electron demand).
Electron withdrawing groups (EWG) on the dienophile and electron donating groups (EDGs) on the diene allow the Diels-Alder to occur at lower temperatures. Please explain this phenomenon in a few words and/or diagrams.
EWGs lower the LUMO of the dienophile. EDGs raise the HOMO of the diene. The difference in energy between the LUMO and HOMO is now smaller, therefore, less heat is required for this reaction to proceed.
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Suggest reagents to accomplish the following transformations. Pay attention to Regiochemistry and Stereochemistry.
Suggest reagents to accomplish the following transformations. Pay attention to Regiochemistry and Stereochemistry.
Suggest reagents to accomplish the following transformations. Pay attention to Regiochemistry and Stereochemistry.
Suggest reagents to accomplish the following transformations. Pay attention to Regiochemistry and Stereochemistry.
Provide the major product for the following reaction
Provide the major product for the following reaction
For the following pair of compounds, CIRCLE the compound that is more basic. Rationalize your answer with structures of the conjugate acid for full credit.
For the following pair of compounds, CIRCLE the compound that is more acidic. Rationalize your answer with structures of the conjugate base for full credit.
Draw the Frost Circle MO diagram of the cyclopropenyl cation and label the MO’s appropriately. Comment on the molecule’s aromatic character.
Please rank the acidity of the following molecules. 1 = Most acidic …. 5 = least acidic.
Explain why the following reaction fails to occur. Please provide an alternative method to do the transformation.
Provide the IUPAC name for the following molecule:
Provide the structure for the following molecule:
meta-isopropylbenzoic acid3
Please draw the endo transition structure for the reaction between (E)-1-methoxy-1,3- butadiene with acrylaldehyde. Please also include the molecular orbitals that are interacting on the transition structure and indicate why this is the preferred lower-energy pathway. Hint: look at the phases of the MO’s.
Please provide arrow-pushing mechanism that accounts for the reaction shown below. Show the formation of both reaction products and clearly label the thermodynamic and kinetic products. Be sure to include all resonance structures, lone pairs, and formal charges in your answer.
Which product would be favored if the reaction were to be conducted at 100 °C? Briefly rationalize your answer.
The thermodynamic product will be favored under these conditions because the reaction is reversible and the more substituted alkene will be the most stable, lowest energy product.
Predict the major product or provide either the reactant(s) or reagents to accomplish each of the following Diels-Alder reactions. Since these reactions result in the formation of chiral molecules, please take stereochemistry into account when deriving your answers.
Propose a detailed mechanism to explain the following reactions. Make sure to draw ALL pertinent resonance structures.
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Provide the major product in the following reaction. If no reaction occurs, write “NR” as the product. Pay attention to Regiochemistry and Stereochemistry!
Suggest reagents to accomplish the following transformations. Pay attention to Regiochemistry and Stereochemistry.
Suggest reagents to accomplish the following transformations. Pay attention to Regiochemistry and Stereochemistry.
Suggest reagents to accomplish the following transformations. Pay attention to Regiochemistry and Stereochemistry.
