Concept explainers
Interpretation:
The majororganic product formed by the addition of
Concept Introduction:
>Addition of hydrogen halides to
This addition may be electrophilic which proceeds through the formation of carbocation intermediates.
>During electrophilic addition, a proton is added to the double bond such that the more stable carbocation is produced.
>The overall addition is according to the Markovnikov rule. The hydrogen atoms get added to the carbon atom which has more hydrogens attached to it.
>The addition of hydrogen halides to alkenes may be through the formation of free radicals as intermediates.
>During free radical addition, the bromine is added to the double bond such that a more stable alkyl free radical is produced.
>The overall addition takes place with a regioselectivity opposite to that of Markovnikov rule: The hydrogen atoms get added to the carbon atom which has less hydrogens attached to it.
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ORGANIC CHEMISTRY,VOL.1 >CUSTOM<
- Addition of HCl to alkene X forms two alkyl halides Y and Z. (A) Label Y and Z as a kinetic or thermodynamic product and explain why. (B) Explain why the addition of HCl occurs at the exocyclic C=C, rather than the other C=Carrow_forwardAddition of HCl to alkene X forms two alkyl halides Y and Z.a.Label Y and Z as a 1,2-addition product or a 1,4-addition product. b. Label Y and Z as the kinetic or thermodynamic product and explain why. c.Explain why addition of HCl occurs at the indicated C=C (called an exocyclic double bond), rather than the other C=C (called an endocyclic double bond).arrow_forward(a) What is the structure of C, which is formed by oxy-Coperearrangement of B with NaOEt? (b) Draw a stepwise mechanism for theconversion of C to the bicyclic alcohol D.arrow_forward
- Bromoetherification, the addition of the elements of Br and OR to adouble bond, is a common method for constructing rings containingoxygen atoms. This reaction has been used in the synthesis of thepolyether antibiotic monensin (Problem 18.34). Draw a stepwisemechanism for the following intramolecular bromoetherification reaction.arrow_forwarda) Draw the mechanism, using good curved arrow notation, for the reaction of 2-methyl-2- butene with bromine in water, omitting any stereochemistry: b) (R)-3-butyn-2-ol is treated with 2 mol of HBr, yielding optically active Compound A (C4H8OBr2). Draw the structure of the reaction with the correct stereochemistry. c) Name Compound A above, including stereochemistry. d) Compound A is treated with HBr to yield Compound B (C4H7Br3). The resulting solution is optically inactive. Draw the product(s) obtained and explain why there is a loss in optical activity.arrow_forwardTreatment of alkenes A and B with HBr gives the same alkyl halide C. Draw a mechanism for each reaction, including all reasonable resonance structures for any intermediate.arrow_forward
- For alkenes A, B, C, and D: (a) Rank A—D in order of increasing heat of hydrogenation; (b) rank A—D in order of increasing rate of reaction with H2, Pd-C; (c) draw the products formed when each alkene is treated with ozone, followed by Zn, H2O.arrow_forwardsusceptible to nucleophilic attack a to b c only a only a and carrow_forwardDraw a stepwise mechanism for the following reaction and explain the stereochemistry of the product.arrow_forward
- Suzuki coupling of aryl iodide A and vinylborane B affords compound C,which is converted to D in the presence of aqueous acid. Identifycompounds C and D and draw a stepwise mechanism for the conversionof C to D.arrow_forwardDraw the major organic product of the reaction. Ignore stereochemistryarrow_forwardWhen both carbons ortho to the aryl oxygen are not bonded to hydrogen, an allyl aryl ether rearranges to a para-substituted phenol. Draw a stepwise mechanism for the following reaction, which contains two [3,3] sigmatropic rearrangements.arrow_forward