Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treat- ment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives which alkene? Account for the stereoselectivity of each B-elimination. H C-C Mẹ Me Br H Ме Br C-C Me Et Et Et Et (A) (В)
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- An alkene having the molecular formula C,H12 is treated sequentially with ozone (O3) and zinc/acetic acid to give the product/s shown. CH3CH2CH,CH½CH2CH Draw a structural formula for the alkene. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. P opy aste Previous NextFollowing are two diastereomers of 3-bromo-4-ethyl-2,3,5-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3-ethyl-2,4,5-trimethyl-3- hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives the E alkene? Br Me H Br Me iPr Et Et iPr iP" iPr bName (including E/Z stereochemistry) the five alkenes that can produce 3-bromo-3-methylhexane on reaction with HBr. Draw the skeletal structure of each molecule.
- An alkene having the molecular formula C5H10 is treated sequentially with ozone (O3) and zinc/acetic acid to give the product/s shown. H3C O CH3CHCH + H. Draw a structural formula for the alkene. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one. P opy aste [* Previous NextA 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.What alkene is needed to synthesize each 1,2-diol using [1] OsO4 followed by NaHSO3 in H2O; or [2] CH3CO3H followed by −OH in H2O?
- Draw the line-angle formula of the enol formed in the following alkyne hydration reaction and then draw the structural formula of the carbonyl compound with which this enol is in equilibrium. -C=CH 1. (sia)2BH 2. NaOH/H₂O₂ an enol carbonyl compound • You do not have to consider stereochemistry. • Draw both the enol and the carbonyl forms. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures using the sign from the drop-down menu. ChemDoodleⓇ <5A In the following reactions, mixtures of alkenes and ethyl ethers are formed. Draw their structures. Explain which is or are likely to be the main product(s) in each reaction. In case of formation of two isomers of alkenes, explain which is formed in greater proportion CH3 ofi H3C- -Br CH3 EtOHAn alkene having the molecular formula C,H14 is treated sequentially with ozone (O3) and zinc/acetic acid to give the product/s shown. Draw a structural formula for the alkene. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. opy aste
- C=CH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-OH HO: Hjö: C=CH c=CH Hö Hg HgThe optically active (2R)-2-phenyl-2-butanol reacts in hydrochloric acid to form haloalkanes and alkenes. The substitution reaction is reported to occur with 100% racemization. Give the structures of the enantiomers that form during the substitution and indicate how much of each is formed. Propose a mechanism for the substitution reaction to yield the R product. What reagents would you use to achieve 100% retention of configuration. Two geometric isomers are obtained during the elimination reaction. Explain mechanistically which alkene will be the main product.Compound A has molecular formula C4H10. Compound A gives two monochlorides, B and C, on photochemical chlorination. Treatment of either of these monochlorides with potassium tert-butoxide gives the same alkene (C4H8) as the product, but B leads to just one isomer of the alkene, D, whereas C gives D and another isomer of the alkene, E. Treatment of monochlorides B and C with aqueous ethanol gives products F and G, respectively, both of which are of molecular formula C4H100. What are the chemical names of compounds A-G?