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- Aromatic iodination can be carried out with a number of reagents, including iodine monochloride, ICl. What is the direction of polarization of ICl? Propose a mechanism for the iodination of an aromatic ring with ICl.The polyurethane foam used for home insulation uses methane-diphenyldiisocyanate (MDI) as monomer. The MDI is prepared by acid-catalyzed reaction of aniline with formaldehyde, followed by treatment with phosgene, COCl2. Propose mechanisms for both steps.Identify the pericyclic reaction benzocyclobutane E undergoes on heating, give astructure for intermediate H, and provide a mechanism that accounts for itsformation.
- What is the expected product of the reaction scheme below?Following is a balanced equation for bromination of toluene.(a) Using the values for bond dissociation enthalpies given in Appendix 3,calculate ∆H0for this reaction.(b) Propose a pair of chain propagation steps and show that they add up to theobserved reaction.(c) Calculate ∆H0for each chain propagation step.(d) Which propagation step is rate-determininExplain the mechanism-Carboxylation—Reaction of RMgX with CO2
- Acetoxybenzene (PhOC(=O)OCH3) is much less reactive than ethoxybenzene (PhOCH2CH3) in electrophilic aromatic substitution reactions. Suggest an explanation for this result, based on an analysis of the inductive and resonance electronic effects of the two substituents on the stability of theWheland intermediate for para substitution by an electrophile E+Unknown X, C5H9Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide,X gives only one product, Y, C5H8. Unlike X, Y decolorizes bromine and changes KMnO4 from purple to brown.Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis–reduction of Y gives dialdehyde Z, C5H8O2. Proposeconsistent structures for X, Y, and Z. Is there any aspect of the structure of X that is still unknown?Tributyltin hydride (Bu3SnH) is used synthetically to reduce alkyl halides, replacing a halogen atom with hydrogen. Free-radical initiators promote this reaction, and free-radical inhibitors are known to slow or stop it. Your job is todevelop a mechanism,
- The following compound undergoes Benzilic Acid Rearrangementto yield ahydroxyacid salt. Proposea mechanism for the reaction, writethe major product,and provide an explanation as tothe preference of migration of one R group over the other.When Br2 is added to buta-1,3-diene at -15 °C, the product mixture contains 60% ofproduct A and 40% of product B. When the same reaction takes place at 60 °C, theproduct ratio is 10% A and 90% B.) Propose a mechanism to account for formation of both A and BCompound A gives the product(s) below on oxidative cleavage with KMnO4 in acidic solution. Propose a structure for A.