2. Write a mechanism for the formation of pentasubstituted benzene 8 from cyclopentadienone 6 and alkyne 7. (Hints: An alkyne can act as a dienophile; start with a Diels-Alder reaction; number the atoms of your starting materials and the product to see where bonds are broken and formed and whether anything is gained or lost overall.) Ph Ph CH3 EtO -- کیسے ہو H 8 -CH3 OEt Heat 6
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- Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.2) Predict the major product for each Diels-Alder reaction. Include stereochemistry where appropriate. H. C=N (a) H H. CH3 CH;O, (b) Ph (c) PhExp3: Diels-Alder reaction Why does cyclopentadiene regularly form a dimer? How to break the dimer into monomers? Does the diene in this reaction act as the nucleophile or the electrophile? Is the maleic anhydride a nucleophile or an electrophile in this reaction? Explain your reasoning.
- The compound below is treated with chlorine in the presence of light. CH-CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. . You do not have to consider stereochemistry. You do not have to explicitly draw H atoms.The compound below is treated with chlorine in the presence of light. H₂C CH3 H3C CH₂CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms.Ethers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of iodoethane with the following alkoxide ion: H3C CH3 + Na You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I, in your answer. P opy aste [*
- 4.- Predict the product for each Diels-Alder reaction. Indicate stereochemistry where appropriate. स a) b) H3C, H3C + H3C CHO A ent 10 150 COOH + ·E· <- c) COOH BAS 5.- Retro Diels-Alder: show a combination of diene and dienophile that would result in each Diels-Alder adduct.A) Write the mechanism and predict the products for the following reaction. Label each product as the thermodynamic product or the kinetic product. Write a few sentences explaining which product would predominate at low temperature and which would predominate at high temperature and explain the reason for this result. HBr ABd B) Choose reagents that would give the following product in a Diels-Alder reaction: C) Predict the major and minor product for the following Diels-Alder reaction:Ethers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of 1-iodo-2-methylpropane with the following alkoxide ic + O Na You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I", in your answer. C opy aste
- b) Which of these dienophiles gives the FASTEST reaction with cyclopentadiene? CH2 CH2 A. | В. C. | D. | Give structures for the major Diels-Alder product of the following reactions: 1,3- cyclohexadiene and tetrachloroethene 1,3-cylcohexadiene and fumaric acid, the trans isomer of maleic acid с.4. Propose a synthesis plan for these molecules (a) (b) Br. OEt from a Wittig reaction from benzene i) Propose a Diels-Alder reaction for the molecule to the left or ii) Draw the mechanism for 3f: (ix)→ (x) CI- CIThe electrophilic aromatic substitution of isopropylbenzene with Br₂ and FeBr, gives 1-bromo-4-isopropylbenzene. :Br: Product of 41-320- bromine and FeBr3 :Br: Fe + HBr FeBr3 Complete the curved-arrow mechanism, beginning with formation of the active brominating reagent. Remember to include lone pairs and formal charges where appropriate.