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1. Explain why the main reaction between acetophenone and anisaldehyde is the mixed aldol reaction rather than (a) self-condensation of acetophenone or (b) Cannizzaro reaction of anisaldehyde. 2. No more than 2 mL of water should be used to dissolve the 2 or 3 pellets of NaOH. Why is not a larger volume of water used? 3. Anisalacetophenone dibromide is much more soluble in CHCl3 than in CCl4. Suggest a reason for this difference. 4. Crystals of pure erythro-anisalacetophenone dibromide are white, whereas crystals of pure anisalacetophenone are light yellow. Suggest a reason for this difference in color. 5. Could trans-anisalacetophenone be isomerized to the cis isomer by irradiating it with UV light? Why or why not? 6. Write out a mechanism that rationalizes the stereochemistry of the formation of erythro- anisalacetophenone dibromide from bromine and trans-anisalacetophenone. 7. Write equations to show the major products from the reactions of the following sets of starting materials: a. propionaldehyde, dilute NaOH b. formaldehyde, concentrated KOH c. trimethylacetaldehyde, acetophenone, dilute NaOH d. p-methoxybenzaldehyde (2 mol), acetone, dilute KOH e. benzaldehyde, methyl propionate, sodium methoxide in methanol 8. Refer to Figures 21.14 and 21.17 and calculate log e for the two maxima in the UV. spectrum of trans-anisalacetophenone and for the single maxima in its dibromide. 9. Why does trans-anisalacetophenone exhibit a maximum in its UV spectrum at substan- tially longer wavelength than does its dibromide? What electronic excitation is responsi- ble for the absorption at longer wavelength?

1. Explain why the main reaction between acetophenone and anisaldehyde is the mixed aldol reaction rather than (a) self-condensation of acetophenone or (b) Cannizzaro reaction of anisaldehyde. 2. No more than 2 mL of water should be used to dissolve the 2 or 3 pellets of NaOH. Why is not a larger volume of water used? 3. Anisalacetophenone dibromide is much more soluble in CHCl3 than in CCl4. Suggest a reason for this difference. 4. Crystals of pure erythro-anisalacetophenone dibromide are white, whereas crystals of pure anisalacetophenone are light yellow. Suggest a reason for this difference in color. 5. Could trans-anisalacetophenone be isomerized to the cis isomer by irradiating it with UV light? Why or why not? 6. Write out a mechanism that rationalizes the stereochemistry of the formation of erythro- anisalacetophenone dibromide from bromine and trans-anisalacetophenone. 7. Write equations to show the major products from the reactions of the following sets of starting materials: a. propionaldehyde, dilute NaOH b. formaldehyde, concentrated KOH c. trimethylacetaldehyde, acetophenone, dilute NaOH d. p-methoxybenzaldehyde (2 mol), acetone, dilute KOH e. benzaldehyde, methyl propionate, sodium methoxide in methanol 8. Refer to Figures 21.14 and 21.17 and calculate log e for the two maxima in the UV. spectrum of trans-anisalacetophenone and for the single maxima in its dibromide. 9. Why does trans-anisalacetophenone exhibit a maximum in its UV spectrum at substan- tially longer wavelength than does its dibromide? What electronic excitation is responsi- ble for the absorption at longer wavelength?

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter23: Addition To A Carbonyl
Section: Chapter Questions
Problem 42CTQ
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Preparation of Anisalacetophenone experiment

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1. Explain why the main reaction between acetophenone and anisaldehyde is the mixed aldol reaction rather than (a) self-condensation of acetophenone or (b) Cannizzaro reaction of anisaldehyde. 2. No more than 2 mL of water should be used to dissolve the 2 or 3 pellets of NaOH. Why is not a larger volume of water used? 3. Anisalacetophenone dibromide is much more soluble in CHCl3 than in CCl4. Suggest a reason for this difference. 4. Crystals of pure erythro-anisalacetophenone dibromide are white, whereas crystals of pure anisalacetophenone are light yellow. Suggest a reason for this difference in color. 5. Could trans-anisalacetophenone be isomerized to the cis isomer by irradiating it with UV light? Why or why not? 6. Write out a mechanism that rationalizes the stereochemistry of the formation of erythro- anisalacetophenone dibromide from bromine and trans-anisalacetophenone. 7. Write equations to show the major products from the reactions of the following sets of starting materials: a. propionaldehyde, dilute NaOH b. formaldehyde, concentrated KOH c. trimethylacetaldehyde, acetophenone, dilute NaOH d. p-methoxybenzaldehyde (2 mol), acetone, dilute KOH e. benzaldehyde, methyl propionate, sodium methoxide in methanol 8. Refer to Figures 21.14 and 21.17 and calculate log e for the two maxima in the UV. spectrum of trans-anisalacetophenone and for the single maxima in its dibromide. 9. Why does trans-anisalacetophenone exhibit a maximum in its UV spectrum at substan- tially longer wavelength than does its dibromide? What electronic excitation is responsi- ble for the absorption at longer wavelength?
Transcribed Image Text:1. Explain why the main reaction between acetophenone and anisaldehyde is the mixed aldol reaction rather than (a) self-condensation of acetophenone or (b) Cannizzaro reaction of anisaldehyde. 2. No more than 2 mL of water should be used to dissolve the 2 or 3 pellets of NaOH. Why is not a larger volume of water used? 3. Anisalacetophenone dibromide is much more soluble in CHCl3 than in CCl4. Suggest a reason for this difference. 4. Crystals of pure erythro-anisalacetophenone dibromide are white, whereas crystals of pure anisalacetophenone are light yellow. Suggest a reason for this difference in color. 5. Could trans-anisalacetophenone be isomerized to the cis isomer by irradiating it with UV light? Why or why not? 6. Write out a mechanism that rationalizes the stereochemistry of the formation of erythro- anisalacetophenone dibromide from bromine and trans-anisalacetophenone. 7. Write equations to show the major products from the reactions of the following sets of starting materials: a. propionaldehyde, dilute NaOH b. formaldehyde, concentrated KOH c. trimethylacetaldehyde, acetophenone, dilute NaOH d. p-methoxybenzaldehyde (2 mol), acetone, dilute KOH e. benzaldehyde, methyl propionate, sodium methoxide in methanol 8. Refer to Figures 21.14 and 21.17 and calculate log e for the two maxima in the UV. spectrum of trans-anisalacetophenone and for the single maxima in its dibromide. 9. Why does trans-anisalacetophenone exhibit a maximum in its UV spectrum at substan- tially longer wavelength than does its dibromide? What electronic excitation is responsi- ble for the absorption at longer wavelength?
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