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Draw the products formed when
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- Two diastereomeric sets of enantiomers, A/B and C/D, exist for 3-bromo-2-butanol. When enantiomer A or B is treated with HBr, only racemic 2,3-dibromobutane is formed; no meso isomer is formed. When enantiomer C or D is treated with HBr, only meso 2,3-dibromobutane is formed; no racemic 2,3-dibromobutane is formed. Account for these observations.arrow_forwardAlcohols undergo an oxidation reaction to yield carbonyl compounds on treatment with CrO3. For example, 2-tert-butylcyclohexanol gives 2-tert-butylcyclohexanone. If axial OH groups are generally more reactive than their equatorial isomers, which do you think reacts faster, the cis isomer of 2-tert-butylcyclohexanol or the trans isomer? Explain.arrow_forwardGive the IUPAC name for each alcoholarrow_forward
- Alkenes can be converted to alcohols by reaction with mercuric acetate to form a ß-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH reduces the C-Hg bond to a C-H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structure of the Hg-containing compound and the final alcohol product formed in the reaction sequence. CH3 Hg(OOCCH3)2 NaBH4 HO™ Oxymercuration product Demercuration Product H₂O, THF Draw the alcohol product of demercuration. Draw the neutral product of oxymercuration. Omit byproducts. OH Hg Incorrectarrow_forwardDraw a structural formula for the major product of the reaction shown.arrow_forwardDraw a structural formula for the major product of the reaction shown. -CH₂CH3 Br₂ H₂O • Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer.arrow_forward
- What reagent is necessary to complete the reaction? CH3-CH2-CH-C-OH ? CHỊCH,CH C-0- Na* CH3 CH3 NaO O NaCl O Na O NaOH + H₂Oarrow_forwardDraw the stereoisomers of 2-methylcyclohexanol.arrow_forwardWhen carbonyl compounds are reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is formed, what will the composition of the product mixture be? Forms more of one enantiomer than another because of steric reasons around the carbonyl Forms more of one enantiomer than another depending on the temperature of the reaction Forms different products depending on the solvent used Forms a racemic mixture of the two possible enantiomersarrow_forward
- Draw a structural formula for the alkene you would use to prepare the alcohol shown by hydroboration/oxidation. OH AFFIL CH3 CH3 H • 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. Sn [F ? ChemDoodlearrow_forwardDraw all stereoisomers formed in the reaction shown. Use wedges and dashes for tetrahedral stereogenic centers, if applicable. OH CH₂CH₂OH HClarrow_forwardacetone H3C, HO H3C OH The product of the following reaction is: A OH H3C OH C D OBarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning