Chemistry Module 2 homework

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Structure Influences Acidity and Basicity Read the instructions carefully and answer the following questions in the space provided. Then attach the PDF file on Discussion Board for peer discussion and peer review 1. In one or two sentences or with an illustration, discuss how each of the

four factors below play a role in determining relative acidity strength. In other words, discuss the general trends, be concise and specific.

a. Periodic Trends b. Resonance c. Induction d. Orbitals


2. Analyze the two compounds below. Circle the structure which is most

acidic overall. Discuss the factors that led you to this choice.

3. Analyze the structure below. Circle the nitrogen atom which is considered

to be overall most basic. Provide a brief discussion to explain why this nitrogen is considered to be most basic (hint: think about the orbital each nitrogen lone-pair occupies). Draw relevant resonance structures of the conjugate acid expected to form when this structure is treated with 1 equivalent of HCl. Underline the resonance structure(s) that have filled octets everywhere.




4. The pKa of the most acidic CH2 group in each of the following compounds

was measured in DMSO as solvent (reference: J. Org. Chem. 1981, 46, 4327–4331.)

Given the pKa data above, propose an explanation why compound 1 is more acidic than compound 3.

Draw the conjugate acid formed and its other relevant resonance structures


Given the pKa data above, propose which of the following two compounds below (5 or 6) is more acidic by comparing the stability of the corresponding conjugate bases. Include (ie. draw) all relevant resonance contributors in your discussion. Do any resonance structures have greater contribution than others to the overall stability? Underline the resonance structure that is considered to be most stable overall.