11-64 The tosylate of (2R,3S)-3-phenyl-2-butanol undergoes E2 elimination on treatment with sodium ethoxide to yield (Z)-2-phenyl-2-butene. Explain, using Newman projections. Na* ¯OCH,CH3 CH3CHCHCH3 CH3C=CHCH3
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- A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.13) Starting with ethyne and any necessary reagents to synthesize enantiomers of (3R,4R)-4-bromo-3-hexanol and (3S,4S)-4-bromo-3-hexanol. H5Ç2 H5Ç2 НО H- HO- Several steps HC ECH H- -Br Br H- C2H5 C2H5The base-promoted rearrangement of an a-haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. Jo Han Sow La NaOH, THF O Nat H3O+ OH NaOH, THF The mechanism involves the following 5 steps: -ō cyclopropanone intermediate 1. Abstraction of a proton to form enolate anion 1; 2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion; 3. Addition of hydroxide ion to form tetrahedral intermediate 3; 4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4; 5. Proton transfer to form the rearranged carboxylic acid. For the following reaction, draw the reaction out on paper, and then draw the structure of cyclopropanone intermediate 2 in the window. 1. NaOH, THF 2. H3O* OH
- Provide the reagents necessary to carry out the following conversion: 4-methyl-cyclohexanol -------> 4-methyl- cyclohexanone O KMNO4/NAOH/H20 peroxyacetic acid O Br2, CCl, O NazCr207/H2SO2/H2O O OsO4lo CI H3C H3C 07 ↔X + :0: OH Dimethylaminopyridine (DMAP) is often used as a catalyst in esterification reactions. A basic solvent such as triethylamine is used to react with the liberated proton from the alcohol group. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CI NMe₂ N(CH₂CH3)3 CH3 6--10-- NMe2: Treatment of (CHa)CHCH(OH)CH,CH3 with TSOH affords two products (M and N) with molecular formula CgH12. The 'H NMR spectra of M and N are given below. Propose structures for M and N and draw a mechanism to explain their formation. 1H NMR of M 3H 1H NMR of N 3H 3H 3 H 1H 3 H 2 H 2H 2H 8 7 6 4 1 0 9 8. 2 1 ppm ppm 4.
- 9a) The proton bonded to the carbon adjacent to the carbonyl group in the following compound can be classified into which chemical shift in the ¹H-NMR spectra of aldehydes and ketones? R or H H - 10.0-12.0 ppm R H -2.0-3.0 ppm NO₂ N (1) 9b) Choose the one below that could be resolved into enantiomers. (1) alpha hydrogens = ? ppm NO₂ NO₂ 9c) Which of the following is the major product of the reaction below. `N H -5.0-7.0 ppm (11) (11) -0.0-1.0 ppm HNO3, H₂SO4 H NO₂ (III) NO₂ (1) and (II) (IV) None of the options (IV)What is the product when (2R, 3R)-2-bromo-2,3-diphenylpentane undergoes an E2 reaction with EtONa? ph Br X (A) H3C, Ph (C) Ph Ph 3 Ph CH₂CH3 (B) H₂C Ph CH₂CH3 CH3 Ph. (D) H₂C Ph R CH₂CH3 Ph Ph Á CH,CH HTreatment of cis-4-bromocyclohexanol with HO− affords compound Aand cyclohex-3-en-1-ol. Treatment of trans-4-bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and Bcontain different functional groups and are not isomers of each other.Propose structures for A and B and offer an explanation for theirformation.
- Provide the structure of the product(s) with stereochemisty if appropriate. If multiple products indicate major product or if products are formed in equal amounts. If there is no reaction expected explain why. (a) OH HIO4 (the protecting group is remained) CHO H HOH2C OH (b) CHO -ОН NaCN # HO -H H -OH CH₂OH (c) CHO HO- -H HO -H NH₂OH 張一 H -OH H -OH CH₂OH i) Ba(OH)2 ii) MeOH, H₂SO4 NaOAc Ac₂0 NaOMe MeOH9-53 Identify the reagents a through d in the following scheme: H OH H. CH30 OCH3 Br BrWhat is an appropriate systematic name for the following? OH CI (1S,2R)-2-hydroxycyclopentanecarbonyl chloride O (15,2 R)-2-hydroxypentanoyl chloride (1R,2S)-2-(chlorocarbonyl)cyclopentanol O (15,5R)-5-hydroxycyclopentanecarbonyl chloride