Concept explainers
Interpretation: A stepwise mechanism for the reaction between benzyl bromide and
Concept introduction: The replacement or substitution of one
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ORGANIC CHEMISTRY-STUDY GDE./SOL.MAN.
- Which reactant in each of the following pairs is more nucleophilic? Explain. (a) -NH2 or NH3 (b) H2O or CH3CO2- (c) BF3 or F- (d) (CH3)3P or (CH3)3N (e) I- or Cl- (f) -C≡N or -OCH3arrow_forwardFluoxetine, a heavily prescribed antidepressant marketed under the name Prozac, can be prepared by a route that begins with reaction between a phenol and an alkyl chloride. (a) The rate of the reaction depends on both phenol and alkyl halide. Is this an SN1 or an SN2 reaction? Show the mechanism. (b) The physiologically active enantiomer of fluoxetine has (S) stereochemistry. Based on your answer in part (a), draw the structure of the alkyl chloride you would need, showing the correct stereochemistry.arrow_forwardRank the following compounds in order of fastest reaction when treated with H2SO4 (1–5, where 1 = fastest), and explain your answer.arrow_forward
- Identify the reagents necessary for the reaction:arrow_forwardTreatment of cis-2-bromocyclohexanol with NaOH yields cyclohexanone instead of an epoxide. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism.arrow_forwardEven though B contains three ester groups, a single Dieckmann product results when B is treated with NaOCH3 in CH3OH, followed by H3O+. Draw the structure and explain why it is the only product formed.arrow_forward
- O-chem help!arrow_forwardWhich reagent would best accomplish the following transformation?arrow_forwardRank the following esters in order of decreasing reactivity in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate):Rank the same esters in order of decreasing reactivity in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).arrow_forward
- 2) When conjugated aldehydes or ketones are attacked by a nucleophile, often more than one product forms. Please show resonance structures to explain which positions in the following conjugated ketone can react with NaBH4. Which product(s) can form? + H н-вн Na H CH3OHarrow_forwardFor the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.arrow_forwardWhich of the attached compound is the most nucleophilic ?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning