Concept explainers
Interpretation:
The major product of the reaction of
Concept introduction:
Fridel-Crafts acylation is a type of electrophilic
Partial rate factor is the experimentally determined relative data for rates of electrophilic aromatic substitution reactions.
Substituents which pull the electron density away from carbon atom are the electron withdrawing substituents.
Substituents which donate the electron density to the carbon atom are the electron releasing substituents.
Electron withdrawing substituents deactivate the ring and direct the upcoming electrophile to meta positions.
Electron releasing substituents activate the ring and direct the upcoming electrophile to ortho-para positions.
Halogen substituents are strongly deactivating but are ortho-para directing.
If aromatic ring having two substituents, the regioselectivity of electrophilic aromatic substitution is controlled by the more activating substituent.
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- In the Friedel-Crafts alkylation of benzene, dialkylation is often a significant by-product. In the Friedel-Crafts acylation of benzene, diacylation is not a significant by-product. Which of the following is the primary reason for this difference? a. Acyl cations are more difficult to make with Lewis acids b.Unlike acyl cations, carbocations can undergo rearrangements. c.Alkyl groups activate the ring to further substitution, acyl groups deactivate it. d. Alkyl groups activate the ring to further substitution, acyl groups deactivate itarrow_forwardShow how you would synthesize nitrobenzene from benzene, using a mixture of nitric acid and sulfuric acid. Write the overall reaction for the preparation of the electrophile and the mechanism for the substitution reactionarrow_forwardThe Friedel-Crafts Alkylation of p-xylene n-propyl bromide can result in an isopropyl as well as n-propyl substitution. A) Write the chemical equation involved in this reaction. B) Which will be the major and minor product? What do you expect will be the ratio of n-propyl to isopropyl substitution for p-xylene?arrow_forward
- The Wittig Reaction allows the preparation of an alkene by the reaction of an aldehyde or ketone with the ylide generated from a phosphonium salt. From the reaction, write the mechanism of Wittig reaction and Wittig reaction applicationarrow_forwardImagine that phenol (“hydroxybenzene”) and nitrobenzene are reacted (in separate beakers) with a hot solution containing both concentrated sulfuric acid and concentrated nitric acid. A) When chlorobenzene reacts with a hot solution of sulfuric and nitric acids, an interesting result occurs: the reaction is slower than the reaction of the solution with benzene – which is similar to the result of the reaction of the solution with nitrobenzene – but it generates products with the same substitution pattern seen in the reaction of the solution with phenol. Explain why chlorobenzene has this curious reactivity.arrow_forwardCalculate theoretical yield of the Grignard reaction synthesis of triphenylmethanol from bromobenzene. Amounts of products used are listed in the image.arrow_forward
- Two mechanisms are among those that have been postulated for decomposition of aryl diazonium salts in aqueous solution containing nucleophilic anions, A—:arrow_forwardAlkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev’s rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak…arrow_forwardAlkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev’s rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak…arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning