The major product of this reaction exists as two stereoisomers. Draw both isomers. Show all hydrogen atoms in the structures. Use wedge and dash bonds to indicate the stereochemistry. You can quickly add condensed hydrogens by clicking the More button and using the +H button. Select Draw Rings More Erase H Br H3C-CH2 H Br-Br H20 H3C CH3 (large excess) > Feedback First, an electrophilic attack of bromine on the double bond results in the formation of a bromonium ion. Next, a nucleophilic attack of water opens the bromonium ion ring. The product of the reaction is a halohydrin. Consider regiochemistry and stercochemistry. 1. Will the intermediate ion be more stable with a positive charge on a tertiary carbon, or on a secondary carbon? 2. Which carbon in the bromonium ring will be attacked by water? 3. In the product, what group is added to the more substituted carbon of the double bond? To the less substituted carbon? Do not forget that you nccd to draw two stcrcoisomers of thc product. Consider the dircction of brominc attack and later attack by water. Check that you have drawn all hydrogens in the structures. Use wedge and dash bonds to indicate the stereochemistry of the isomers.
Basics in Organic Reactions Mechanisms
In organic chemistry, the mechanism of an organic reaction is defined as a complete step-by-step explanation of how a reaction of organic compounds happens. A completely detailed mechanism would relate the first structure of the reactants with the last structure of the products and would represent changes in structure and energy all through the reaction step.
Heterolytic Bond Breaking
Heterolytic bond breaking is also known as heterolysis or heterolytic fission or ionic fission. It is defined as breaking of a covalent bond between two different atoms in which one atom gains both of the shared pair of electrons. The atom that gains both electrons is more electronegative than the other atom in covalent bond. The energy needed for heterolytic fission is called as heterolytic bond dissociation energy.
Polar Aprotic Solvent
Solvents that are chemically polar in nature and are not capable of hydrogen bonding (implying that a hydrogen atom directly linked with an electronegative atom is not found) are referred to as polar aprotic solvents. Some commonly used polar aprotic solvents are acetone, DMF, acetonitrile, DMSO, etc.
Oxygen Nucleophiles
Oxygen being an electron rich species with a lone pair electron, can act as a good nucleophile. Typically, oxygen nucleophiles can be found in these compounds- water, hydroxides and alcohols.
Carbon Nucleophiles
We are aware that carbon belongs to group IV and hence does not possess any lone pair of electrons. Implying that neutral carbon is not a nucleophile then how is carbon going to be nucleophilic? The answer to this is that when a carbon atom is attached to a metal (can be seen in the case of organometallic compounds), the metal atom develops a partial positive charge and carbon develops a partial negative charge, hence making carbon nucleophilic.
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