A reasonable mechanism that accounts for the given reaction is to be proposed. Concept introduction: An electrophile is an electron deficient species that is attacked by a nucleophile, which is an electron-rich species. Alkenes can undergo acid-catalyzed hydration reactions in which the alkenes are treated with water in the presence of strong acids. The major product for these reactions is an alcohol. Water ( H + and HO - ) adds across the double bonded carbon atoms according to the Markovnikov’s rule. The addition of water to an alkene favors the product in which the proton adds to the alkene carbon that is initially bonded to a greater number of hydrogen atoms (to the least substituted carbon atom), thus forming a stable carbocation intermediate. The rearrangement of the carbocation intermediate may be possible. Finally, a proton transfer reaction must take place to form an uncharged product. For the double bond present outside of the ring, the methyl carbons in the ring migrate, which converts the more strained ring to a less strained ring. These reactions are called ring expansion reactions, which involve migration of carbon.

Question

Want to see the full answer?

Answer 1

Question

Chapter 11, Problem 11.58P

Interpretation Introduction

Interpretation:

A reasonable mechanism that accounts for the given reaction is to be proposed.

Concept introduction:

An electrophile is an electron deficient species that is attacked by a nucleophile, which is an electron-rich species. Alkenes can undergo acid-catalyzed hydration reactions in which the alkenes are treated with water in the presence of strong acids. The major product for these reactions is an alcohol.

Water (H+and HO-) adds across the double bonded carbon atoms according to the Markovnikov’s rule. The addition of water to an alkene favors the product in which the proton adds to the alkene carbon that is initially bonded to a greater number of hydrogen atoms (to the least substituted carbon atom), thus forming a stable carbocation intermediate. The rearrangement of the carbocation intermediate may be possible. Finally, a proton transfer reaction must take place to form an uncharged product.

For the double bond present outside of the ring, the methyl carbons in the ring migrate, which converts the more strained ring to a less strained ring. These reactions are called ring expansion reactions, which involve migration of carbon.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Using reaction free energy to predict equilibrium composition Consider the following equilibrium: 2NOCI (g) 2NO (g) + Cl2 (g) AGº =41. kJ Now suppose a reaction vessel is filled with 4.50 atm of nitrosyl chloride (NOCI) and 6.38 atm of chlorine (C12) at 212. °C. Answer the following questions about this system: ? rise Under these conditions, will the pressure of NOCI tend to rise or fall? x10 fall Is it possible to reverse this tendency by adding NO? In other words, if you said the pressure of NOCI will tend to rise, can that be changed to a tendency to fall by adding NO? Similarly, if you said the pressure of NOCI will tend to fall, can that be changed to a tendency to rise by adding NO? yes no If you said the tendency can be reversed in the second question, calculate the minimum pressure of NO needed to reverse it. Round your answer to 2 significant digits. 0.035 atm ✓ G 00. 18 Ar

Highlight each glycosidic bond in the molecule below. Then answer the questions in the table under the drawing area. HO- HO- -0 OH OH HO NG HO- HO- OH OH OH OH NG OH

€ + Suppose the molecule in the drawing area below were reacted with H₂ over a platinum catalyst. Edit the molecule to show what would happen to it. That is, turn it into the product of the reaction. Also, write the name of the product molecule under the drawing area. Name: ☐ H C=0 X H- OH HO- H HO- -H CH₂OH ×