Given that, when an unsymmetrical alkene such as propene is treated with NBS in aqueous dimethyl sulfoxide, the major product has the bromine atom bonded to the less highly substituted carbon atom. Whether the orientation is Markovnikov or non-Markovnikov is to be explained. Concept introduction: NBS can be used as a source of bromine, as it is stable, easily handled compound that slowly decompose in aqueous dimethyl sulfoxide to yield bromine at controlled rate. Bromine from NBS adds on to the double bond to give a cyclic bromonium ion. Water, being a nucleophile, attacks the bromonium ion from the unshielded side to give an intermediate which loses a proton to yield a bromohydrin as the product. The addition occurs with anti stereochemistry. According to Markovnikov rule, in the addition of HX to unsymmetrical alkenes the H (positive part) attaches itself to the carbon with fewer alkyl substituents and X (negative part) attaches itself to the carbon with more alkyl substituents. To explain: Whether the orientation of groups in the addition reaction between propene and NBS in aqueous dimethyl sulfoxide ,where in the major product has the bromine atom bonded to the less highly substituted carbon atom, is Markovnikov or non-Markovnikov.

Question

For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

Answer 1

Question

Chapter 8.3, Problem 6P

Interpretation Introduction

Interpretation:

Given that, when an unsymmetrical alkene such as propene is treated with NBS in aqueous dimethyl sulfoxide, the major product has the bromine atom bonded to the less highly substituted carbon atom. Whether the orientation is Markovnikov or non-Markovnikov is to be explained.

Concept introduction:

NBS can be used as a source of bromine, as it is stable, easily handled compound that slowly decompose in aqueous dimethyl sulfoxide to yield bromine at controlled rate. Bromine from NBS adds on to the double bond to give a cyclic bromonium ion. Water, being a nucleophile, attacks the bromonium ion from the unshielded side to give an intermediate which loses a proton to yield a bromohydrin as the product. The addition occurs with anti stereochemistry.

According to Markovnikov rule, in the addition of HX to unsymmetrical alkenes the H (positive part) attaches itself to the carbon with fewer alkyl substituents and X (negative part) attaches itself to the carbon with more alkyl substituents.

To explain:

Whether the orientation of groups in the addition reaction between propene and NBS in aqueous dimethyl sulfoxide ,where in the major product has the bromine atom bonded to the less highly substituted carbon atom, is Markovnikov or non-Markovnikov.

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