Elimination occurs when (Z)-3-bromohex-3-ene is treated with NaNH2. Under the same conditions, 1-bromocyclohexeneundergoes elimination much more sluggishly. Explain why
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Elimination occurs when (Z)-3-bromohex-3-ene is treated with NaNH2.
Under the same conditions, 1-bromocyclohexene
undergoes elimination much more sluggishly. Explain why
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- When (ft)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (fl)-2-bromo-2,5- dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.Draw the products formed when both cis- and trans-but-2-ene are treated with a peroxyacid followed by -OH (in H2O).Explain how these reactions illustrate that anti dihydroxylation is stereospecic.Draw the structure of an alkyl bromide with molecular formula C-H₁3Br that fits each description: (a) a 1° alkyl bromide with one stereogenic center; (b) a 2° alkyl bromide with two stereogenic centers; (c) an achiral 3° alkyl bromide.
- If 2,4-dimethylcyclopentane-1-carbonyl chloride reacts with propan-2-ol. What product is obtained?Dehydrohalogenation of 1-chloro-1-methylcyclopropane affords two alkenes (A and B) as products. Explain why A is the major product despite the fact that it contains the less substituted double bond.Addition of HCl to alkene X forms two alkyl halides Y and Z. (A) Label Y and Z as a kinetic or thermodynamic product and explain why. (B) Explain why the addition of HCl occurs at the exocyclic C=C, rather than the other C=C
- (a) Draw the products (including stereoisomers) formed when 2methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.explain why cis-2-chloro-1-cyclohexanol yields a cyclohexanone but the trans isomer yields cyclohexene oxideWhen buta-1,3-diene (CH2 = CH – CH = CH2) is treated with HBr, two constitutional isomers are formed, CH3CHBrCH = CH2 and BrCH2CH = CHCH3. Draw a stepwise mechanism that accounts for the formation of both products.
- What product is formed when each compound undergoes thermal electrocyclic ring opening or ring closure? Label each process as conrotatory or disrotatory, and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds.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?Draw the products (including stereoisomers) formed when (S)-2,4-dimethylhex-2-ene is treated with HBr and peroxides under similarconditions.