Concept explainers
Interpretation:
The formation of
Concept introduction:
The replacement or substitution of one
The electron deficient chemical species that contains positive charge or have a deficiency of electrons are known as an electrophile.
In an electrophilic
In electrophilic aromatic substitution, if the ring bears several substituents, then the orientation is controlled by the most activating substituent.
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ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
- The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.arrow_forwardWrite the etherification reactions of isopropyl bromide and 2-bromo-1-nitropropane with phenol . Which reaction takes place faster and why?arrow_forwardIn an aqueous solution containing sodium bicarbonate, aniline reacts quickly with bromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions, however, and the yields (mostly m-nitroaniline) are poor.Explain why nitration of aniline is so sluggish and why it gives mostly metasubstitution.arrow_forward
- What would the major organic reaction product be from the reaction of 1-bromo-1-methylcyclopentane withsodium hydroxide? Would the elimination reaction outcome be affected if a student accidentally adds sodium tertbutoxide instead of sodium hydroxide?arrow_forwardBecause bromocyclohexane is a secondary alkyl halide, both cyclohexanol and cyclohexene are formed when the alkyl halide reacts with hydroxide ion. Suggest a method to synthesize cyclohexanol from bromocyclohexane that forms little or no cyclohexene.arrow_forwardThe reaction of 3,4-dimethyl-3-hexanol (3,4-dimethylhexan-3-ol) with HBr generates compound A as the major product. Treatment of compound A with a strong base gives two isomers of compound B as the major product, along with one isomer of compound C and one isomer of compound D as minor products, all of which have one double-bond equivalent. Identify compounds A, B, C, and D and give their names. By what mechanism does the reaction of 3,4-dimethyl-3-hexanol with HBr occur? By what mechanism does the reaction of A with strong base to form B occur? Propose reaction conditions for an alternative, one-step method for converting 3,4-dimethyl-3-hexanol directly to compound B.arrow_forward
- 7. Compound X is an alcohol. Upon oxidation by acidify potassium permanganate, a ketone, Y is formed. X reacts with phosphorous bromide (PBR3) to give Z which is then purified and reflux in dry ether along with Mg metal to form a Grignard reagent, S. S is then treated with Y to yield 3,4-di methyl-3-hexanol after hydrolysis in dilute HCI. Identify X,Y, Z and S. Write all the chemical equations for the reaction involved.arrow_forwardA graduate student tried to make o-fluorophenylmagnesium bromide by adding magnesium to an ether solution of o-fluorobromobenzene. After obtaining puzzling results with this reaction, she repeated the reaction by using as solvent some tetrahydrofuran that contained a small amount of furan. From this reaction, she isolated a fair yield of the compound that follows. Propose a mechanism for its formation.arrow_forwardThe structure below is the cyclic ether (epoxide), butene oxide: (1) CH3CH₂ -CH₂ butene oxide How could this compound be prepared from but-1-ene? Explain why butene oxide is much more reactive than its isomer, tetrahydrofuran, which is also a cyclic ether: H₂C-CH₂ H₂C CH₂ tetrahydrofuran Illustrate how butene oxide reacts with ammonia, showing details of the mechanism leading to the final product, C4H11 NO.arrow_forward
- 1. What effect would you expect on the rate of reaction of ethanol with 2-iodo-2-methyl-butane if the concentration of the halide is tripled? 2. Explain the difference between addition, elimination and substitutionreactions. 3. Optically active 2-butanol slowly racemizes on standing in dilute sulfuricacid. Propose a mechanism to account for this observation.arrow_forward1. When cyclopentene is allowed to react with bromine in an aqueous solution of sodium chloride, the products of the reaction are trans-1,2-dibromocyclopentane, trans-1-bromo-2-chlorocyclopentane, and trans-2-bromo-1-cyclopentanol. Write mechanisms to account for the formation of all these products.arrow_forwardPossible alternative brominations include: Veratrole (1,2-dimethoxybenzene) to 1,2-dibromo-4,5-dimethoxybenzene; 4-Methylacetanilide to 2-bromo-4-methylacetanilide; 2-Methylacetanilide (made in experiment S.1) to 4-bromo-2-methylacetanilide; Vanillin to 5-bromovanillin; Acetanilide to 4-bromoacetanilide; a. b. C. d. e. EXPERIMENT S4: BROMINATION OF AROMATIC COMPOUNDS Certain other acetanilides made in experiment S.1 may also be used as precursors in this experiment. Estimated time: 1 afternoon Associated learning goals: Section 6, LG 6.6; Section 7, LG 7.2 and 7.4 Pre-lab report: complete the standard report form, and answer the following questions. In this experiment, molecular bromine (Br2) is generated from the redox reaction of potassium bromate with hydrobromic acid. Write a balanced equation for this process. Briefly outline the mechanism by which Br2 brominates your aromatic compound. Why do the bromine atoms end up at the positions indicated rather than anywhere else in the…arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning