Propose a set of conditions for a series of reactions that would produce the lactone from the carboxylic acid shown below. Conditions should include solvents, temperature, reagents, and order of operations. OH ?
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- Propose a mechanism for the acid-catalyzed hydration of propene. Remember that a mechanism must include curved arrows to show movement of electrons, as well as all intermediates.Provide the mechanism of the protecting group using the following reagents below.Give reagents necessary and show isolated intermediates for the synthesis below.
- Provide a mechanism for the decarboxylation reaction below:Give the major organic product(s) that would be expected on reaction of 3-pentanone (shown right) with 1 equivalent of LDA, followed by addition of 1 equivalent of each of the following reagents.If methanol rather than water is added at the end of a Hell–Volhard–Zelinskii reaction, an ester rather than an acid is produced. Show how you would carry out the following transformation, and propose a mechanism for the ester forming step.
- A chemist in need of 2,2-dimethylpentanoic acid decided to synthesize some by reaction of 2-chloro-2-methylpentane with NaCN, followed by hydrolysis of the product. After the reaction sequence was carried out, however, none of the desired product could be found. What do you suppose went wrong?Predict the products of the reaction of the below reagents with either acetophenone or phenylacetaldehyde. NaBH4, H3O+ HCN, KCN H2NNH2 CH3MgBr, then H3O+ NH2OH, catalytic acidPropose a plausible arrow pushing mechanism for the following transformation. Hint: hydrolysis of acetal followed by ester formation.
- Show two different ways to synthesize the following compound by carbonyl condensation, and then say which one is better.Propose an easy synthesis route to obtain 2‐nitro‐4‐pentylphenol starting from bromobenzene, without using the Stille reaction:The 1H NMR spectra for two esters with molecular formula C8H8O2 are shown next. Which of the esters is hydrolyzed more rapidly in an aqueoussolution with a pH of 10?