This addition of HBr to (Z)-2-bromobut-2-ene takes place regioselectively, with the Br preferentially adding to the alkene C that does not already possess a Br atom. (a) Provide a detailed mechanism for this reaction, including initiation and propagation steps. (b) Explain why this regiochemistry is observed. Br Br HBr ROOR Br
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- Bromination can occur in a 1,4 fashion across conjugated double bonds, as shown here for cyclohexa-1,3-diene. One mechanism that has been proposed involves a five-membered ring, bromonium ion intermediate, as shown below. (a) According to this mechanism, what should the stereochemistry be for the products-namely, all cis, all trans, or a mixture of both? (b) Observations from experiment show that both cis and trans products are formed. Does this support or discredit the proposed mechanism shown here? Br Br2 Cyclohexa-1,3-diene Br :Br: Br: Br:For each reaction, draw the complete mechanism and the major organic product(s), paying attention to stereochemistry. (a) (b) OH LOH (еxcess) ? ? CH,Cl2 CH2CI2When treated with NaOH, the bromide below gives an alkene by the E2 mechanism, by elimination of the H atom indicated by the arrow: (a) Draw the Newman projection from which elimination takes place. (b) Draw the mechanism. (c) Draw the product with the proper stereochemistry. (d) Assign the proper stereochemical descriptor to the product. (e) Give the rate equation
- (c) The following reaction shows the electrophillc addition reaction between an alkene compound with hydrogen chloride, HCI. Tindak balas berikut menunjukkan tindak balas penambahan elektrofilik antara sebatian alkena dengan hidrogen klorida, HCI. HCI Major product Draw the mechanism for the formation of major product. Lukis mekanisma bagi pembentukan hasil utama berikut.Alkenes can be converted to alcohols by hydroboration-oxidation. (a) Draw the structure of the alcohol or alcohols formed in the reaction sequence. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond and two O Hint in-plane bonds per each chiral carbon. Draw hydrogen atoms that are connected to wedge-and-dash bonds.(b) Characterize the product or products of the reactions. The first step of the reaction, hydroboration, involves addition of BH, to the double bond, with -BH, attached to one carbon and hydrogen Be sure to draw hydrogens on oxygen, where applicable. attached to the other. Consider both Rings the regioselectivity and the Select Draw More Erase stereochemistry of this addition. H Diborane, B,H,, is a source of borane, BH,, and can be used 1. B2H6, interchangeably. Diglyme is a solvent. diglyme 2. H2О2, НО", The product or products of the reaction are characterized as being O S. O racemic. O achiral. O R,S (and/or S,R). O R. O S,S. O R.R. O diastereomers.Draw mechanism arrows and then predict the major products and stereochemistry. Also include the labels of thermodynamic and kinetic 1-methylcyclohexene with BH3 followed later with –OH, H2O2, and H2O.
- When benzyl bromide is treated separately with KI and CH3OH, the substitution products are different but the reaction rates are about the same. KI Br (a) What does this suggest about the mechanism-is it SN1 or SN2? Explain. (b) Draw the complete mechanism (including curved arrows) for the formation of each product. (c) If the concentration of KI were doubled, what would happen to the rate of the substitution reaction? HOCH3 ?Propene reacts with hydrogen bromide to form two isomers, the major product being, 2- bromopropane. 1(c) Draw the mechanism of the reaction of hydrogen bromide with propene to form 1- bromopropane and 2-bromopropane, showing the structure of both intermediates. (i) (ii) Explain why 2-bromopropane is the major product.In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer ispresent. For example, treatment of optically pure 1-bromo-1phenylpropane with water forms 1-phenylpropan-1-ol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Which product predominates—the product of inversion or the product of retention of configuration? (c) Suggest an explanation for this phenomenon.
- In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1-phenylpropan-1-ol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Which product predominates—the product of inversion or the product of retention of configuration? (c) Suggest an explanation for this phenomenon.A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a) Draw the resonance forms of the three possible allylic free radical intermediates.10) Consider the following alkene hydration reaction. он H2SO, H20 Given that the reaction is endergonic by 10 kcal/mol, complete the following. (a) Draw the intermediate(s) formed in the mechanistic pathway to the major product in the indicated space below. If there are multiple intermediates label them 1, 2, 3, 4, etc. (b) Sketch a reaction-energy profile for this reaction and clearly label staring material, product, intermediate(s), transition state(s), AG" and AG (of the rate determining step) on your plot. Progress of the reaction Draw and Label Intermediate(s) Below: Potential energy