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Develop a synthesis for the following molecule using only the indicated materials as sources for the carbon atoms that appear in the final product. As a hint, you will need to draw upon several reactions from earlier chapters to come up with a successful solution, and you may have to use some of the carbon sources more than one time. Also assume that
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Chapter 20 Solutions
EBK ORGANIC CHEMISTRY
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- Convert 2-pentanol into 2,3-dibromopentane. Draw structures of the starting material (2-pentanol) and final product (2,3-dibromopentane), and show the two reactions needed for this synthesis. Include the structure of the intermediate compound, and the reagents and conditions for each reaction. Then explain why 1,2-dibromopentane would not be a significant product of this synthesis.arrow_forwardStarting with benzene and using any other reagents of your choice, design a synthesis for the following compound: Br XX O₂N The target molecule above can be prepared by treating benzene with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A HNO3, H₂SO4 D Fuming H₂SO4 B E Br2, AlBr3 Dilute H₂SO4 C BrMg F MgBr axxa. AICI 3arrow_forwardPropose a synthesis for the following molecule from starting material/reagents containing 6 carbons or less. Be sure to show all reagents and synthetic intermediates in your answer. You do not need to show reaction mechanisms.arrow_forward
- Starting with benzene and using any other reagents of your choice, design a synthesis for the following compound: The target molecule above can be prepared by treating benzene with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A OEt 1) EtMgBr 2) H₂O* D NaOEt, heat B HNO3, H₂SO4 E NaOH, heat с F Cl₂, AICI3 CH3CH₂COCI, AICIarrow_forwardStarting with benzene and using any other reagents of your choice, design a synthesis for the following compound: COOH NO₂ COOH The target molecule above can be prepared by treating benzene with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A Mel, AlCl3 B KMnO4, NaOH, heat (followed by H3O+ workup) C HCI, Zn D E F (CH3)2CHCI, AICI 3 HNO3, H2SO4 Fuming H2SO4arrow_forwardWrite four examples of the condensation reactions of carbonyl compounds, starting with benzaldehyde (C6H5CHO), with appropriate reagents and appropriate reactions. Write down the mechanism of one you want in detail.arrow_forward
- 10. Propose a multi-step synthesis to prepare para-nitrotoluene from benzene. NOTE: You can just provide the description or name of the reaction, you do not have to provide the actual reagents.arrow_forwardStarting from acetylene and alkyl halides not longer than 4 carbon atoms, show the synthesis of 3-octanol and a ketone. Indicate the reagents in each step. You may use more than one mole of the reactants.arrow_forwardWrite a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOH Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.arrow_forward
- In attempting to make 2-bromo-2-methyl-propane from 2-methyl-propene, as shown below, you used a dilute aqueous solution of hydrobromic acid. Upon analysis of the isolated product, you realize there is a major unwanted by-product. Br a) Based on the reaction conditions used, predict the major by-product and show a mechanism for its formation. b) What should be changed in the reaction conditions described in order to completely avoid the formation of the unwanted by-product?arrow_forwardHow would the following conversion be achieved? Please show the reaction mechanism step by steparrow_forwardYou are a chemistry company's latest chemistry recruit and your first job is to prepare 2-methylcyclohexanol. The one key starting material you have been given is methylcyclohexane. Draw a scheme to take you from the starting material to the product outlining the reagents you would use for each step as well as the key organic product(s) formed from each step. [Note: You do not need to show mechanisms for any steps]arrow_forward
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