Chapter 3, Problem 142EQ

Question: How do quantum mechanical effects influence the stability and reactivity of molecules with non-classical carbocations, such as the 2-norbornyl cation, and how does this impact the reaction mechanisms and outcomes?

Ring opening reaction of tetrahydrofuran catalyzed by basic materials

write the free radical monosubtitution mechanism for the bromination of ethane to produce bromoethane

The Friedel-Crafts Alkylation of p-xylene n-propyl bromide can result in an isopropyl as well as n-propyl substitution. A) Write the chemical equation involved in this reaction. B) Which will be the major and minor product? What do you expect will be the ratio of n-propyl to isopropyl substitution for p-xylene?

Write the mechanism and predict the product for the reaction of cyclohexene with bromine. Make sure that you include the stereochemistry for the reaction in your mechanism. Then describe in detail the appearance of the reactants and products in this reaction. What would be the visible evidence that a reaction took place? Explain paragraph why no color change would occur upon mixing cyclohexanol with a solution of bromine.

The Wittig reaction can be used for the synthesis of conjugated dienes as the example below, 1-phenyl-penta-1, 3-diene.  Propose two different sets of reagents that could be combined in a Wittig reaction to give 1-phenyl-1,3-pentadiene.

Conversion of an alkene to a halohydrin and internal displacement of a halide ion by an alkoxide ion are both stereoselective. Use this information to demonstrate that the configuration of the alkene is preserved in the epoxide. As an illustration, show that reaction of cis-2-butene by this two-step sequence gives cis-2,3- dimethyloxirane (cis-2-butene oxide).

Write a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. A. Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond.   B. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond.   C.Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Cl- will act as the base in this reaction.

Show stereo chemistry and possible outcomes and the steps for the reaction.