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The following scheme shows possible interconversions between alkenes, alkyl halides, alcohols and ethers. Study it carefully and answer the questions that follow. (x) (iii) (ix) (i) (viii) OH OH (iv) CN (vii) (V) (vi) Br Br он OH .1 Give reagents and conditions for step (i). What reagent would you use to reverse the process i.e., convert the depicted alkyl chloride back to the starting alcohol? (2) .2 Give reagents and conditions for step (ii), as well as the detailed reaction mechanism that explains formation of the depicted product. What other product is possible from this reaction? Please explain (6) .3 Give the reagent and conditions for step (iii). (2) .4 Give a reagent and conditions for step (iv), as well as a detailed reaction mechanism. Why is the depicted alkene the only product and not any other alkene? (5) 5 Give reagents and conditions for step (v). (1) 6 Give a reagent and conditions for step (vi). If you wanted to produce the cis-diol directly from the alkene, what reagents would you use? (2) .7 Give a reagent and conditions for step (vii), as well as the detailed reaction mechanism that explains formation of the depicted product. (5) 8 Give reagents and conditions for step (viii). Why is the original stereochemistry of the alcohol retained in the product? Please give a brief explanation (not a reaction mechanism). (3) 9 Give reagents and conditions for step (ix). (1) 10 Give reagents and conditions for step (x). (3) 11 Give reagents and conditions that can cleave the ether product of step (viii) and show what products you will get. Please give a detailed reaction mechanism that explains the outcome of the reaction. (6) 2 12 Draw all the possible stereoisomers of the diol product of step (vi) and assign the stereochemistry at all chiral centers. In groups of two, designate which stereoisomers are enantiomers and which ones are diastereomers. (4)

The following scheme shows possible interconversions between alkenes, alkyl halides, alcohols and ethers. Study it carefully and answer the questions that follow. (x) (iii) (ix) (i) (viii) OH OH (iv) CN (vii) (V) (vi) Br Br он OH .1 Give reagents and conditions for step (i). What reagent would you use to reverse the process i.e., convert the depicted alkyl chloride back to the starting alcohol? (2) .2 Give reagents and conditions for step (ii), as well as the detailed reaction mechanism that explains formation of the depicted product. What other product is possible from this reaction? Please explain (6) .3 Give the reagent and conditions for step (iii). (2) .4 Give a reagent and conditions for step (iv), as well as a detailed reaction mechanism. Why is the depicted alkene the only product and not any other alkene? (5) 5 Give reagents and conditions for step (v). (1) 6 Give a reagent and conditions for step (vi). If you wanted to produce the cis-diol directly from the alkene, what reagents would you use? (2) .7 Give a reagent and conditions for step (vii), as well as the detailed reaction mechanism that explains formation of the depicted product. (5) 8 Give reagents and conditions for step (viii). Why is the original stereochemistry of the alcohol retained in the product? Please give a brief explanation (not a reaction mechanism). (3) 9 Give reagents and conditions for step (ix). (1) 10 Give reagents and conditions for step (x). (3) 11 Give reagents and conditions that can cleave the ether product of step (viii) and show what products you will get. Please give a detailed reaction mechanism that explains the outcome of the reaction. (6) 2 12 Draw all the possible stereoisomers of the diol product of step (vi) and assign the stereochemistry at all chiral centers. In groups of two, designate which stereoisomers are enantiomers and which ones are diastereomers. (4)

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
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.43P: The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas...
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The following scheme shows possible interconversions between alkenes, alkyl halides, alcohols and

ethers. Study it carefully and answer the questions that follow

The following scheme shows possible interconversions between alkenes, alkyl halides, alcohols and ethers. Study it carefully and answer the questions that follow. (x) (iii) (ix) (i) (viii) OH OH (iv) CN (vii) (V) (vi) Br Br он OH .1 Give reagents and conditions for step (i). What reagent would you use to reverse the process i.e., convert the depicted alkyl chloride back to the starting alcohol? (2) .2 Give reagents and conditions for step (ii), as well as the detailed reaction mechanism that explains formation of the depicted product. What other product is possible from this reaction? Please explain (6) .3 Give the reagent and conditions for step (iii). (2) .4 Give a reagent and conditions for step (iv), as well as a detailed reaction mechanism. Why is the depicted alkene the only product and not any other alkene? (5) 5 Give reagents and conditions for step (v). (1) 6 Give a reagent and conditions for step (vi). If you wanted to produce the cis-diol directly from the alkene, what reagents would you use? (2) .7 Give a reagent and conditions for step (vii), as well as the detailed reaction mechanism that explains formation of the depicted product. (5) 8 Give reagents and conditions for step (viii). Why is the original stereochemistry of the alcohol retained in the product? Please give a brief explanation (not a reaction mechanism). (3) 9 Give reagents and conditions for step (ix). (1) 10 Give reagents and conditions for step (x). (3) 11 Give reagents and conditions that can cleave the ether product of step (viii) and show what products you will get. Please give a detailed reaction mechanism that explains the outcome of the reaction. (6) 2 12 Draw all the possible stereoisomers of the diol product of step (vi) and assign the stereochemistry at all chiral centers. In groups of two, designate which stereoisomers are enantiomers and which ones are diastereomers. (4)
Transcribed Image Text:The following scheme shows possible interconversions between alkenes, alkyl halides, alcohols and ethers. Study it carefully and answer the questions that follow. (x) (iii) (ix) (i) (viii) OH OH (iv) CN (vii) (V) (vi) Br Br он OH .1 Give reagents and conditions for step (i). What reagent would you use to reverse the process i.e., convert the depicted alkyl chloride back to the starting alcohol? (2) .2 Give reagents and conditions for step (ii), as well as the detailed reaction mechanism that explains formation of the depicted product. What other product is possible from this reaction? Please explain (6) .3 Give the reagent and conditions for step (iii). (2) .4 Give a reagent and conditions for step (iv), as well as a detailed reaction mechanism. Why is the depicted alkene the only product and not any other alkene? (5) 5 Give reagents and conditions for step (v). (1) 6 Give a reagent and conditions for step (vi). If you wanted to produce the cis-diol directly from the alkene, what reagents would you use? (2) .7 Give a reagent and conditions for step (vii), as well as the detailed reaction mechanism that explains formation of the depicted product. (5) 8 Give reagents and conditions for step (viii). Why is the original stereochemistry of the alcohol retained in the product? Please give a brief explanation (not a reaction mechanism). (3) 9 Give reagents and conditions for step (ix). (1) 10 Give reagents and conditions for step (x). (3) 11 Give reagents and conditions that can cleave the ether product of step (viii) and show what products you will get. Please give a detailed reaction mechanism that explains the outcome of the reaction. (6) 2 12 Draw all the possible stereoisomers of the diol product of step (vi) and assign the stereochemistry at all chiral centers. In groups of two, designate which stereoisomers are enantiomers and which ones are diastereomers. (4)
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