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A student set about the conversion of compound 1 into compound 2; however, the student used too much of the required reagent. As a result, they obtained a mixture of compounds 1 and 2, as well as compounds 3 and 4. Compound Structure 1 2 3 4 ал OH an OH aso (a) What type of reaction is the conversion of 1 to 2 (e.g., substitution, elimination, etc.)? Reduction (b) What reagent can be used to convert the unexpected compound 3 back into the desired product 2? PCC (there are others that are okay too) (c) As the product of this reaction turned out to be a mixture, the student set about separating these four compounds. First, they dissolved the mixture in dichloromethane and extracted this solution with dilute, aqueous hydrochloric acid. This gave an aqueous phase V and an organic phase X, which were separated from one another. Aqueous phase V was treated with excess sodium bicarbonate, and then was extracted with dichloromethane. This dichloromethane layer was placed into flask A. Organic phase X was washed with aqueous sodium bicarbonate to give another aqueous layer Y and organic layer Z, which were separated from one another. Aqueous layer Y was treated with excess aqueous hydrochloric acid and extracted with diethyl ether. This diethyl ether phase was placed in flask B. Lastly, organic layer Z was evaporated to dryness and the remaining compounds were separated by column chromatography using silica gel. Compounds were eluted from the column with appropriate mobile phases that were placed into flasks C, D, and E, respectively, in order of elution. The compound in flask C showed a peak in the IR spectrum at 1745 cm-1, whereas that in flask D showed a peak at 1700 cm-¹. Indicate the NUMBER(S) of the compound(s) that ended up in each flask. As there are only four compounds but five flasks, one flask will not contain a compound (indicate NONE for this flask): Flask A Compound NONE B 1 с 4 D 2 E 3

A student set about the conversion of compound 1 into compound 2; however, the student used too much of the required reagent. As a result, they obtained a mixture of compounds 1 and 2, as well as compounds 3 and 4. Compound Structure 1 2 3 4 ал OH an OH aso (a) What type of reaction is the conversion of 1 to 2 (e.g., substitution, elimination, etc.)? Reduction (b) What reagent can be used to convert the unexpected compound 3 back into the desired product 2? PCC (there are others that are okay too) (c) As the product of this reaction turned out to be a mixture, the student set about separating these four compounds. First, they dissolved the mixture in dichloromethane and extracted this solution with dilute, aqueous hydrochloric acid. This gave an aqueous phase V and an organic phase X, which were separated from one another. Aqueous phase V was treated with excess sodium bicarbonate, and then was extracted with dichloromethane. This dichloromethane layer was placed into flask A. Organic phase X was washed with aqueous sodium bicarbonate to give another aqueous layer Y and organic layer Z, which were separated from one another. Aqueous layer Y was treated with excess aqueous hydrochloric acid and extracted with diethyl ether. This diethyl ether phase was placed in flask B. Lastly, organic layer Z was evaporated to dryness and the remaining compounds were separated by column chromatography using silica gel. Compounds were eluted from the column with appropriate mobile phases that were placed into flasks C, D, and E, respectively, in order of elution. The compound in flask C showed a peak in the IR spectrum at 1745 cm-1, whereas that in flask D showed a peak at 1700 cm-¹. Indicate the NUMBER(S) of the compound(s) that ended up in each flask. As there are only four compounds but five flasks, one flask will not contain a compound (indicate NONE for this flask): Flask A Compound NONE B 1 с 4 D 2 E 3

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter9: Nucleophilic Substitution And Β-elimination
Section: Chapter Questions
Problem 9.45P: Draw a structural formula for the major organic product of each reaction and specify the most likely...
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Please be specific and explain why the compounds end up in that order. thank you

A student set about the conversion of compound 1 into compound 2; however, the student used too much of the required reagent. As a result, they obtained a mixture of compounds 1 and 2, as well as compounds 3 and 4. Compound Structure 1 2 3 4 ал OH an OH aso (a) What type of reaction is the conversion of 1 to 2 (e.g., substitution, elimination, etc.)? Reduction (b) What reagent can be used to convert the unexpected compound 3 back into the desired product 2? PCC (there are others that are okay too) (c) As the product of this reaction turned out to be a mixture, the student set about separating these four compounds. First, they dissolved the mixture in dichloromethane and extracted this solution with dilute, aqueous hydrochloric acid. This gave an aqueous phase V and an organic phase X, which were separated from one another. Aqueous phase V was treated with excess sodium bicarbonate, and then was extracted with dichloromethane. This dichloromethane layer was placed into flask A. Organic phase X was washed with aqueous sodium bicarbonate to give another aqueous layer Y and organic layer Z, which were separated from one another. Aqueous layer Y was treated with excess aqueous hydrochloric acid and extracted with diethyl ether. This diethyl ether phase was placed in flask B. Lastly, organic layer Z was evaporated to dryness and the remaining compounds were separated by column chromatography using silica gel. Compounds were eluted from the column with appropriate mobile phases that were placed into flasks C, D, and E, respectively, in order of elution. The compound in flask C showed a peak in the IR spectrum at 1745 cm-1, whereas that in flask D showed a peak at 1700 cm-¹. Indicate the NUMBER(S) of the compound(s) that ended up in each flask. As there are only four compounds but five flasks, one flask will not contain a compound (indicate NONE for this flask): Flask A Compound NONE B 1 с 4 D 2 E 3
Transcribed Image Text:A student set about the conversion of compound 1 into compound 2; however, the student used too much of the required reagent. As a result, they obtained a mixture of compounds 1 and 2, as well as compounds 3 and 4. Compound Structure 1 2 3 4 ал OH an OH aso (a) What type of reaction is the conversion of 1 to 2 (e.g., substitution, elimination, etc.)? Reduction (b) What reagent can be used to convert the unexpected compound 3 back into the desired product 2? PCC (there are others that are okay too) (c) As the product of this reaction turned out to be a mixture, the student set about separating these four compounds. First, they dissolved the mixture in dichloromethane and extracted this solution with dilute, aqueous hydrochloric acid. This gave an aqueous phase V and an organic phase X, which were separated from one another. Aqueous phase V was treated with excess sodium bicarbonate, and then was extracted with dichloromethane. This dichloromethane layer was placed into flask A. Organic phase X was washed with aqueous sodium bicarbonate to give another aqueous layer Y and organic layer Z, which were separated from one another. Aqueous layer Y was treated with excess aqueous hydrochloric acid and extracted with diethyl ether. This diethyl ether phase was placed in flask B. Lastly, organic layer Z was evaporated to dryness and the remaining compounds were separated by column chromatography using silica gel. Compounds were eluted from the column with appropriate mobile phases that were placed into flasks C, D, and E, respectively, in order of elution. The compound in flask C showed a peak in the IR spectrum at 1745 cm-1, whereas that in flask D showed a peak at 1700 cm-¹. Indicate the NUMBER(S) of the compound(s) that ended up in each flask. As there are only four compounds but five flasks, one flask will not contain a compound (indicate NONE for this flask): Flask A Compound NONE B 1 с 4 D 2 E 3
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