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Reagents a. HCI b. HBr c. H₂O, H₂SO4 d. Br₂ e. Cl₂ f. H₂, Pd 9. Br₂, H₂O h. Cl₂, H₂O i. OsO4 then NaHSO3 j. k. 1. HC=CH Hg(OAc)2. H₂O then NaBH4 BH3 then H₂O₂, NaOH O3 then (CH3)2S m. n. 0. p. q. r. 2 equivalents of NaNH₂ H₂, Lindlar's catalyst Na/NH3 H₂SO4, HgSO4 (sia) 2BH then H₂O₂, NaOH 1 equivalent of NaNH₂ In this synthesis starting with acetylene, reagents from the table are used to carry out the indicated steps (shown in blue). In the box below, draw the structure of compound h.

Reagents a. HCI b. HBr c. H₂O, H₂SO4 d. Br₂ e. Cl₂ f. H₂, Pd 9. Br₂, H₂O h. Cl₂, H₂O i. OsO4 then NaHSO3 j. k. 1. HC=CH Hg(OAc)2. H₂O then NaBH4 BH3 then H₂O₂, NaOH O3 then (CH3)2S m. n. 0. p. q. r. 2 equivalents of NaNH₂ H₂, Lindlar's catalyst Na/NH3 H₂SO4, HgSO4 (sia) 2BH then H₂O₂, NaOH 1 equivalent of NaNH₂ In this synthesis starting with acetylene, reagents from the table are used to carry out the indicated steps (shown in blue). In the box below, draw the structure of compound h.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Organic Chemistry Synthesis Exercise** **Reagents:** a. HCl b. HBr c. H₂O, H₂SO₄ d. Br₂ e. Cl₂ f. H₂, Pd g. Br₂, H₂O h. Cl₂, H₂O i. OsO₄ then NaHSO₃ j. Hg(OAc)₂, H₂O then NaBH₄ k. BH₃ then H₂O₂, NaOH l. O₃ then (CH₃)₂S m. 2 equivalents of NaNH₂ n. H₂, Lindlar's catalyst o. Na / NH₃ p. H₂SO₄, HgSO₄ q. (sia)₂BH then H₂O₂, NaOH r. 1 equivalent of NaNH₂ In this synthesis starting with acetylene, reagents from the table are used to carry out the indicated steps (shown in blue). In the box below, draw the structure of **compound h**. **Instructions:** - Use the wedge/hash bond tools to indicate stereochemistry where it exists. - In cases where there is more than one answer, just draw one. - Show stereochemistry in a meso compound. - Do not include counter-ions, e.g., Na⁺, I⁻, in your answer. (Note: Utilize the drawing tools provided below to represent the chemical structure.) **[Drawing Tools Instructions]**
Transcribed Image Text:**Organic Chemistry Synthesis Exercise** **Reagents:** a. HCl b. HBr c. H₂O, H₂SO₄ d. Br₂ e. Cl₂ f. H₂, Pd g. Br₂, H₂O h. Cl₂, H₂O i. OsO₄ then NaHSO₃ j. Hg(OAc)₂, H₂O then NaBH₄ k. BH₃ then H₂O₂, NaOH l. O₃ then (CH₃)₂S m. 2 equivalents of NaNH₂ n. H₂, Lindlar's catalyst o. Na / NH₃ p. H₂SO₄, HgSO₄ q. (sia)₂BH then H₂O₂, NaOH r. 1 equivalent of NaNH₂ In this synthesis starting with acetylene, reagents from the table are used to carry out the indicated steps (shown in blue). In the box below, draw the structure of **compound h**. **Instructions:** - Use the wedge/hash bond tools to indicate stereochemistry where it exists. - In cases where there is more than one answer, just draw one. - Show stereochemistry in a meso compound. - Do not include counter-ions, e.g., Na⁺, I⁻, in your answer. (Note: Utilize the drawing tools provided below to represent the chemical structure.) **[Drawing Tools Instructions]**
**Synthesis Pathway Using Organic Chemistry Roadmaps** **Diagram Explanation:** The diagram provides a synthesis map for transforming various compounds using specific reagents. The process starts with the base compound (HC≡CH) and progresses through multiple steps, resulting in different final compounds. - **Compound Overview:** - **Compound a**: Formed from the base compound HC≡CH using reagent r. - **Compound b**: Formed from HC≡CH using reagent n. - **Compound c**: Derived from HC≡CH using reagent b. - **Compound d**: Produced from compounds a and c. - **Compound e**: Created from HC≡CH using reagent a. - **Compound f**: Formed from compound d using reagent r. - **Compound g**: Obtained from compound e using reagent f. - **Compound h**: Synthesized from compounds f and g. - **Compound i**: Developed from compound h using reagent n. - **Compound j**: Final compound, produced from compound i using reagent i. **Reagents List:** a. HCl b. HBr c. H₂O, H₂SO₄ d. Br₂ e. Cl₂ f. Na, NH₃ g. (sia)₂BH then H₂O₂, NaOH h. O₃, (CH₃)₂S i. 1. O₃, 2. H₂O j. NaBH₄ k. H₂, Pd-C l. KMnO₄, H₃O⁺ m. 2 equivalents of NaNH₂ n. H₂, Lindlar's catalyst o. Na / NH₃ p. H₂SO₄, HgSO₄ This roadmap illustrates how different reagents are utilized for specific transformations within an organic synthesis pathway. Each step corresponds to a specific reaction, advancing through the synthesis sequence.
Transcribed Image Text:**Synthesis Pathway Using Organic Chemistry Roadmaps** **Diagram Explanation:** The diagram provides a synthesis map for transforming various compounds using specific reagents. The process starts with the base compound (HC≡CH) and progresses through multiple steps, resulting in different final compounds. - **Compound Overview:** - **Compound a**: Formed from the base compound HC≡CH using reagent r. - **Compound b**: Formed from HC≡CH using reagent n. - **Compound c**: Derived from HC≡CH using reagent b. - **Compound d**: Produced from compounds a and c. - **Compound e**: Created from HC≡CH using reagent a. - **Compound f**: Formed from compound d using reagent r. - **Compound g**: Obtained from compound e using reagent f. - **Compound h**: Synthesized from compounds f and g. - **Compound i**: Developed from compound h using reagent n. - **Compound j**: Final compound, produced from compound i using reagent i. **Reagents List:** a. HCl b. HBr c. H₂O, H₂SO₄ d. Br₂ e. Cl₂ f. Na, NH₃ g. (sia)₂BH then H₂O₂, NaOH h. O₃, (CH₃)₂S i. 1. O₃, 2. H₂O j. NaBH₄ k. H₂, Pd-C l. KMnO₄, H₃O⁺ m. 2 equivalents of NaNH₂ n. H₂, Lindlar's catalyst o. Na / NH₃ p. H₂SO₄, HgSO₄ This roadmap illustrates how different reagents are utilized for specific transformations within an organic synthesis pathway. Each step corresponds to a specific reaction, advancing through the synthesis sequence.
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