Which of the following describes the sigmatropic rearrangement that occurs in the reaction shown below? CH2 CH3 dede CH3 CH₂ [3,3] sigmatropic rearrangement [2,3] sigmatropic rearrangement [1,4] sigmatropic rearrangement [1,3] sigmatropic rearrangement [1,5] sigmatropic rearrangement
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- A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2 CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under the same conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C. Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structures of A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions.A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under thesame conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C.Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structuresof A, B, and C; give equations for their formation; and explain the stereospecificity of these reactionsOct-1-yne (HC≡CCH2CH2CH2CH2CH2CH3) reacts rapidty with NaH, forming a gas that bubbles out of the reaction mixture, as one product. Oct-1-yne also reacts rapidty with CH3MgBr, and a different gas is produced. Write balanced equations for both reactions and identify the gases formed.
- Which stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br2 and H2O?Complete the following reaction scheme. Give all product(s) and indicate major or minor and any relevant stereochemistry (g) 1) BH3. THF 2) H202, OH (h) 1) Hg(OАC), H,о 2) NABH4Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: CH3 CH3 CH3 HBr Br Br cis & trans cis & trans However, similar reaction of HBr with 3-bromocyclohexene produces a single product, trans-1,2-dibromocyclohexane: Br Br HBr "Br Propose a structure for an ionic intermediate that is responsible for the unique regiochemistry and stereochemistry of the reaction of 3-bromocyclohexene with HBr.
- Two products are formed in the following [1,7] sigmatropic rearrangement, one due to hydrogen migration and the other to deuterium migration. Showthe configuration of the products by replacing A and B with the appropriate atoms (H or D).a) What product is formed from the [1,7] sigmatropic rearrangement of a deuterium in the following triene? (b) Does this reaction proceed in a suprafacial or antarafacial manner under thermal conditions? (c) Does this reaction proceed in a suprafacial or antarafacial manner under photochemical conditions?Two products are formed in the following [1,7] sigmatropic rearrangement, one due to hydrogen migration and the other to deuterium migration. Show the configuration of the products by replacing A and B with the appropriate atoms (H or D).
- What is the stereochemistry of the nitrile produced in the reaction below? CN NaCN CCH3 Br CH,CH,CHCH3 DMSO (S)-isomer 1:1 mixture of (R)- and (S) isomer O (S)-isomer an unequal mixture of (R)- and (S) isomer O (R)-isomer HIFollowing is an outline of a synthesis of bombykol, the sex attractant of the male silk- worm moth. Of the four stereoisomers possible for this conjugated diene, the 10-trans- 12-cis isomer shown here is over 106 times more potent as a sex attractant than any of the other three possible stereoisomers. H H ÓMe ÓMe trans 12 cis HO (3) ÓMe Bombykol C16H3,0 Show how this synthesis might be accomplished and explain how your proposed syn- thesis is stereoselective for the 10-trans-12-cis isomer.: 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.