Video Solution: Each of the following reactions has been described in the ch...

Sign up for free to keep watching this solution
Organic Chemistry / Leaving Group Conversions - Using HX / Problem #15920

Each of the following reactions has been described in the chemical literature and involves an organic starting material somewhat more complex than those we have encountered so far. Nevertheless, on the basis of the topics covered in this chapter, you should be able to write the structure of the principal organic product of each reaction. 

Treatment of alcohol A with HCl (catalyst) in CH3OH as the solvent produces 3 different polyenes B, C, and D that have the same molecular formula (MF= C9H16O) and contain only trans alkenes. Predict the structures of B, C and D.

b.  Which one of the alkenes B, C, D will be favored under thermodynamic or kinetic control? Explain your answer in 1-2- sentences.

Watch Solution

Predict the organic product of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product. Draw your answer in skeletal form. You will be graded on the product your draw from the reaction no other information is needed for this question.

Watch Solution

Predict the organic product of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product. Draw your answer in skeletal form. You will be graded on the product your draw from the reaction no other information is needed for this question.

Watch Solution

Predict the major product for the following reaction

A) I                             B) II                            C) III                          D) IV                          E) V          

Watch Solution

Provide an organic reaction in which the given intermediate or transition-state structure is involved and give a chemical equation for your selected organic reaction that includes the following in each of your answers:

(i) structural formula(s) for the organic reactant(s) [Be sure to show stereochemistry clearly when necessary.];

(ii) a structural formula for the major organic product [Be sure to show stereochemistry clearly when necessary.];

(iii) the experimental conditions (Give structural formulas for organic compounds. Give a chemical formula for inorganic reactants or catalysts . If heat and/or light is needed, be sure to indicate it appropriately.) As we do for most organic reaction equations, the chemical equations that you give do not need to be balanced. Be sure to show stereochemistry clearly when necessary.

Watch Solution

Give the best reagent(s) for the following reactions to occur (in the box). Include solvents if applicable. Indicate the reaction type (ex. SN2) on the line next to the product. Indicate the reaction type (ex. SN2/E2/SN1/E1) on the line next to the product box.

Watch Solution

The transformation of the hydroxyl group into a good leaving group can be accomplished through the use of various reagents. 

Watch Solution

Provide a complete mechanism for the following transformation.

Watch Solution

Predict the major product of the reaction shown.

Watch Solution

Compound A reacts with HBr via an SN1 process leading to 3 different constitutional isomers. Draw the structure of these products.

Watch Solution

The following reaction below is probably

 

A) an SN1-type reaction involving the protonated alcohol as the substrate.

B) an SN2 -type reaction involving the protonated alcohol as the substrate.

C) an E1 -type reaction involving the protonated alcohol as the substrate.

D) an E2 -type reaction involving the protonated alcohol as the substrate.

E) an epoxidation reaction.

Watch Solution