Account for the fact that allylic bromination of 1-octene by NBS gives these products. NBS Br CH,Clg Br 1-Octene 3-Bromo-1-octene (E)-1-Bromo-2-octene (83%) (racemic, 17%)
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A: The elimination reaction occurs when (Z)-3-bromohex-3-ene is treated with NaNH2 is as shown below.
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- 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 reactions2. What is the IUPAC name of the following alkene? (A) (3E,5Z)-3-bromoocta-3,5-diene (B) (3Z,5E)-6-bromoocta-3,5-diene C (3E,5Z)-3-bromoocta-4,6-diene (D) (32,5E)-3-bromoocta-3,5-diene (E) (3E,5Z)-3-bromohepta-3,5-dienc Br 3,5 8Draw the structure consistent with each description. a.(2E,4E)-octa-2,4-diene in the s-trans conformation b.(3E,5Z)-nona-3,5-diene in the s-cis conformation c.(3Z,5Z)-4,5-dimethyldeca-3,5-diene. Draw both the s-cis and s-trans conformations.
- Addition of HBr to allene (CH2=C=CH2) forms 2-bromoprop-1-ene ratherthan 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed froman allylic carbocation. Considering the arrangement of orbitals in theallene reactant, explain this result.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.Which isomer of 1-bromo-3-isopropylcyclohexane reacts faster when refluxed with potassium tert-butoxide, the cis isomer or the trans isomer? Draw the structure of the expected product from the faster-reacting compound.
- C(CH3)3X +H20 where (X-F, CI, Br, I) give reaction with each of halogen as well determine with which halogen substitution reaction is more favorable and feasible and give reason of its feasibility? C(CH3)3OHChemistry 60. Give the principal product(s) expected, if any, when trans-1,3-pentadiene reacts under the following conditions. Assume one equivalent of each reagent reacts unless noted otherwise. (a) H2O, H3O+ (b) Na+EtO- in EtOH (c) Maleic anhydride heatDraw the structure of (Z)-1-bromo-1-chloro-1-butene. • Consider E/Z stereochemistry of alkenes. • You do not have to explicitly draw H atoms. AAVII ? ChemDoodle [F Ⓡ
- Using the Woodward–Hoffmann rules, predict the stereochemistry of eachreaction.a. a [6 + 4] thermal cycloadditionb. photochemical electrocyclic ring closure of deca-1,3,5,7,9-pentaenec. a [4 + 4] photochemical cycloadditiond. a thermal [5,5] sigmatropic rearrangementFrom trans-1-chloro-2-isopropylcyclohexane, only 3-isopropylcyclohexene, the less substituted alkene, is formed. Using conformational analysis, explain why this product is observed. Also, will the E2 reaction with trans-1-chloro- 2-isopropylcyclohexane or cis-1-chloro-2-isopropylcyclohexane occur faster under the same basic conditions? CH;O Na* CH3OH CI trans-1-Chloro-2 (R)-3-Isopropylcyclohexene isopropylcyclohexaneDraw the structure of each compound.a. (Z)-penta-1,3-diene in the s-trans conformationb. (2E,4Z)-1-bromo-3-methylhexa-2,4-dienec. (2E,4E,6E)-octa-2,4,6-triened. (2E,4E)-3-methylhexa-2,4-diene in the s-cis conformation