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COOEt COOEt Step 1 Step 2 Step 3 COOEt COOEt COOH Step 6 OH Step 4 Step 7 (racemic) cyclizes under conditions (8) OTS Step 5 Step 8 ОН OH (racemic) Frontalin (racemic) Shown above are the steps in one of the several published syntheses of Frontalin, a pheromone of the western pine beetle. From the choices provided, show the reagents and conditions by which step 3 of this synthesis might be accomplished. List the reagent(s) in order that will accomplish this transformation. No more than 4 steps are required. List your answer as a single letter (single-step transformation) or a series of letters (multi-step transformation) with no commas separating them. For example, "ab" corresponds to: 1. Eto Na+ 2. NaOH, H₂O NOTE: The order in which you list your letters matters! Reagents: a. Eto Na* g. NaCN b. NaOH, H₂O h. SOCI₂ c. H3O+, heat i. (CH3)2CuLi, ether, -78°C d. LiAlH4 j. H₂O e. p-TsCI, pyridine k. RCO3H f. Br I. H3O+ 1,024

COOEt COOEt Step 1 Step 2 Step 3 COOEt COOEt COOH Step 6 OH Step 4 Step 7 (racemic) cyclizes under conditions (8) OTS Step 5 Step 8 ОН OH (racemic) Frontalin (racemic) Shown above are the steps in one of the several published syntheses of Frontalin, a pheromone of the western pine beetle. From the choices provided, show the reagents and conditions by which step 3 of this synthesis might be accomplished. List the reagent(s) in order that will accomplish this transformation. No more than 4 steps are required. List your answer as a single letter (single-step transformation) or a series of letters (multi-step transformation) with no commas separating them. For example, "ab" corresponds to: 1. Eto Na+ 2. NaOH, H₂O NOTE: The order in which you list your letters matters! Reagents: a. Eto Na* g. NaCN b. NaOH, H₂O h. SOCI₂ c. H3O+, heat i. (CH3)2CuLi, ether, -78°C d. LiAlH4 j. H₂O e. p-TsCI, pyridine k. RCO3H f. Br I. H3O+ 1,024

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 27AP
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COOEt COOEt Step 1 Step 2 Step 3 COOEt COOEt COOH Step 6 OH Step 4 Step 7 (racemic) cyclizes under conditions (8) OTS Step 5 Step 8 ОН OH (racemic) Frontalin (racemic) Shown above are the steps in one of the several published syntheses of Frontalin, a pheromone of the western pine beetle. From the choices provided, show the reagents and conditions by which step 3 of this synthesis might be accomplished. List the reagent(s) in order that will accomplish this transformation. No more than 4 steps are required. List your answer as a single letter (single-step transformation) or a series of letters (multi-step transformation) with no commas separating them. For example, "ab" corresponds to: 1. Eto Na+ 2. NaOH, H₂O NOTE: The order in which you list your letters matters! Reagents: a. Eto Na* g. NaCN b. NaOH, H₂O h. SOCI₂ c. H3O+, heat i. (CH3)2CuLi, ether, -78°C d. LiAlH4 j. H₂O e. p-TsCI, pyridine k. RCO3H f. Br I. H3O+ 1,024
Transcribed Image Text:COOEt COOEt Step 1 Step 2 Step 3 COOEt COOEt COOH Step 6 OH Step 4 Step 7 (racemic) cyclizes under conditions (8) OTS Step 5 Step 8 ОН OH (racemic) Frontalin (racemic) Shown above are the steps in one of the several published syntheses of Frontalin, a pheromone of the western pine beetle. From the choices provided, show the reagents and conditions by which step 3 of this synthesis might be accomplished. List the reagent(s) in order that will accomplish this transformation. No more than 4 steps are required. List your answer as a single letter (single-step transformation) or a series of letters (multi-step transformation) with no commas separating them. For example, "ab" corresponds to: 1. Eto Na+ 2. NaOH, H₂O NOTE: The order in which you list your letters matters! Reagents: a. Eto Na* g. NaCN b. NaOH, H₂O h. SOCI₂ c. H3O+, heat i. (CH3)2CuLi, ether, -78°C d. LiAlH4 j. H₂O e. p-TsCI, pyridine k. RCO3H f. Br I. H3O+ 1,024
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