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.
Want to see the full answer?
Check out a sample textbook solutionChapter 13 Solutions
Organic Chemistry - Standalone book
- A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_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_forwardthe following reaction scheme leads to the formation of compound B. give the structure of the final products and of the intermediate product A and justify, using the mechanism, the formation of thesearrow_forward
- Write the structures of all the alkenes that can be formed by dehydrohalogenation of the following alkyl halides using sodium ethoxide. Assuming that Zaitsev's rule applies, predict the alkene formed in greatest amount in each case.arrow_forward1-pentanol + NaBr/H2SO4 -> 1-bromopentane Is this substitution reaction reversible? In other words, would one expect to obtain an equilibrium mixture of the alcohol and bromoalkene at the end of the reaction of would one expect this reaction to go to completion? Justify your answer?arrow_forwardGive the order of reactivity of carboxylic acid and its derivatives. What is thesignificance of this order of reactivity in predicting their interconversions?arrow_forward
- Explain with the help of electronic effects, ‘generally haloalkenes undergo nucleophilic substitution reactions whereas haloarenes undergo electrophilic substitution reactions’.arrow_forwardThe following table indicates the yield percent values of nitration products and toluene bromination. Explain the difference between the performance percentages of the products of bromination.arrow_forwardThe formation of the following cyclic compound has been observed in the hydration of the following alkene, write a mechanism that explains the product.arrow_forward
- Assuming that benzaldehyde is the limiting reagent for the synthesis of stilbene, that stilbene is the limiting reagent for the synthesis of stilbene dibromide, and that stilbene dibromide is the limiting reagent for the synthesis of diphenylacetylene; what is the overall % yield of diphenylacetylene from benzaldehyde given the percentage yield of each step of the reaction sequence as follows? Give only two significant digits. If the answer is a whole number with two digits, do not include the decimal. benza Idehy de Notes: 66% stil be ne 23% stilbene dibromi de 66% dipheny lacetyle nearrow_forwardAssuming that benzaldehyde is the limiting reagent for the synthesis of stilbene, that stilbene is the limiting reagent for the synthesis of stilbene dibromide, and that stilbene dibromide is the limiting reagent for the synthesis of diphenylacetylene; what is the overall % yield of diphenylacetylene from benzaldehyde given the percentage yield of each step of the reaction sequence as follows? Give only two significant digits. If the answer is a whole number with two digits, do not include the decimal. 52% 87% benzaldehyde → stilbene → stilbene dibromide 41% Answer: diphenylacetylene Notes: For our multi-step synthesis we cannot just calculate the yield based on starting amount of benzaldehyde and final amount of diphenylacetylene because your group may have been supplemented with commercial material at one or more steps. In truth most chemist use an excess of the least expensive reagent to increase their yield. So in our case benzyltriphenylphosphonium chloride should probably be our…arrow_forwardPropanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4. The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning