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Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol a. LiAlH4 f. PBr3 b. H₂SO4 9. CrO3, H₂ SO4, H₂O c. HCI h. NaH d. HBr e. SOCI₂ Reagents available i. CH3 MgBr; then H3O+ j. CH3 CH₂ MgBr; then H3O+ k. CH3CH₂ CH₂ MgBr; then H3O+ I. C6H5 MgBr (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+ n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3

Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol a. LiAlH4 f. PBr3 b. H₂SO4 9. CrO3, H₂ SO4, H₂O c. HCI h. NaH d. HBr e. SOCI₂ Reagents available i. CH3 MgBr; then H3O+ j. CH3 CH₂ MgBr; then H3O+ k. CH3CH₂ CH₂ MgBr; then H3O+ I. C6H5 MgBr (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+ n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 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
Chapter6: Reactions Of Alkenes
Section: Chapter Questions
Problem 6.54P
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**Synthesis of the Compound: Step-by-Step Guide** *Objective:* Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown in the diagram. If the synthesis requires only two steps, enter "none" for step 3. **Compound Diagram:** A skeletal chemical structure is shown, which needs to be identified as the target compound for synthesis. --- **Alcohol Starting Materials:** 1. Methanol 2. Ethanol 3. 1-Propanol 4. 2-Propanol 5. Cyclohexanol **Reagents Available:** - a. LiAlH₄ - b. H₂SO₄ - c. HCl - d. HBr - e. SOCl₂ - f. PBr₃ - g. CrO₃, H₂SO₄, H₂O - h. NaH - i. CH₃MgBr; then H₃O⁺ - j. CH₃CH₂MgBr; then H₃O⁺ - k. CH₃CH₂CH₂MgBr; then H₃O⁺ - l. C₆H₅MgBr (phenylmagnesium bromide); then H₃O⁺ - m. (CH₃)₂CHMgBr; then H₃O⁺ - n. Dess-Martin periodinane (DMP) --- *Write the number/letters of the alcohol/reagents in the boxes below:* - **Alcohol Starting Material:** [ ] - **Reagent for Step 1:** [ ] - **Reagent for Step 2:** [ ] - **Reagent for Step 3:** [ ] **Instructions:** Choose the appropriate alcohol starting material and list the required reagents in the sequence to achieve the desired synthesis.
Transcribed Image Text:**Synthesis of the Compound: Step-by-Step Guide** *Objective:* Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown in the diagram. If the synthesis requires only two steps, enter "none" for step 3. **Compound Diagram:** A skeletal chemical structure is shown, which needs to be identified as the target compound for synthesis. --- **Alcohol Starting Materials:** 1. Methanol 2. Ethanol 3. 1-Propanol 4. 2-Propanol 5. Cyclohexanol **Reagents Available:** - a. LiAlH₄ - b. H₂SO₄ - c. HCl - d. HBr - e. SOCl₂ - f. PBr₃ - g. CrO₃, H₂SO₄, H₂O - h. NaH - i. CH₃MgBr; then H₃O⁺ - j. CH₃CH₂MgBr; then H₃O⁺ - k. CH₃CH₂CH₂MgBr; then H₃O⁺ - l. C₆H₅MgBr (phenylmagnesium bromide); then H₃O⁺ - m. (CH₃)₂CHMgBr; then H₃O⁺ - n. Dess-Martin periodinane (DMP) --- *Write the number/letters of the alcohol/reagents in the boxes below:* - **Alcohol Starting Material:** [ ] - **Reagent for Step 1:** [ ] - **Reagent for Step 2:** [ ] - **Reagent for Step 3:** [ ] **Instructions:** Choose the appropriate alcohol starting material and list the required reagents in the sequence to achieve the desired synthesis.
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