What product is formed when (CH3C=CHCH,COCH2CH,CO,CH,CH3 is treated with each reagent: (a) H2 (1 equiv), Pd-C; (b) H2 (2 equiv), Pd-C; (c) LIAIH4, followed by H,O; (d) NABH,, CH;OH?
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- A key step in the synthesis of the narcotic analgesic meperidine (tradename Demerol) is the conversion of phenylacetonitrile to X. (a) What isthe structure of X? (b) What reactions convert X to meperidine ?Hydrogenation of alkene A with D2 in the presence of Pd-C affords a single product B. Keeping this result in mind, what compound is formed when A is treated with each reagent: (a) mCPBA; (b) Br2, H2O followed by base? Explain these results.Hydrogenation of alkene A with D2 in the presence of Pd-C affords asingle product B. Keeping this result in mind, what compound is formedwhen A is treated with each reagent: (a) mCPBA; (b) Br2, H2O followedby base? Explain these results.
- Hydrogenation of alkene A with D2 in the presence of Pd-C affords a single product B. Keeping this result in mind, what compound is formed whenA is treated with each reagent: (a) mCPBA; (b) Br2, H2O followed by base? Explain these results.Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular formula C10H16, both yield 2,6- dimethyloctane when treated with H2 and a Pd catalyst. Ozonolysis of oximene forms (CH3)2C = O, CH2 = O, CH2(CHO)2, and CH3COCHO. Ozonolysis of myrcene yields (CH3)2C = O, CH2 = O, (two equiv), and HCOCH2CH2COCHO. Identify the structures of oximene and myrcene.Explain the following result. Acetic acid (CH3COOH), labeled at its OH oxygen with theuncommon 18O isotope (shown in red), was treated with aqueous base, and then the solution was acidified. Two products having the 18O label at different locations were formed.
- Devise a synthesis of attached acetal from 1-bromo-2-methylhexane,alcohols (and diols) containing one or two carbons, and any neededinorganic reagents.Draw all of the substitution and elimination products formed from thegiven alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate thestereochemistry around the stereogenic centers present in the products,as well as the mechanism by which each product is formed.Explain the following result. Acetic acid (CH3COOH), labeled at its OH oxygen with theuncommon 18O isotope (shown in red), was treated with aqueous base, and then the solution was acidied. Two products having the 18O label at different locations were formed.
- What product is formed when CH3OCH2CH2C ≡ CCH2CH(CH3)2 is treated with each reagent: (a) H2 (excess), Pd-C; (b) H2(1 equiv), Lindlar catalyst; (c) H2 (excess), Lindlar catalyst; (d) Na, NH3?Identify F in the following reaction sequence. F was converted in several steps to the antidepressant paroxetine (trade name Paxil; see also Problem 9.9).a) Which reaction yields hexan-1-ol?