Video Solution: Write a sequence of steps depicting the mechanisms of each o...

Sign up for free to keep watching this solution

Write a sequence of steps depicting the mechanisms of each of the following reactions. Use curved arrows to show electron flow.

 

Predict the organic product(s) for the following reaction. Be sure to indicate stereochemistry when appropriate. If stereoisomers are produced draw one and state the relationship between the otherstereoisomer formed. (enantiomers, diastereomers, etc.).

Watch Solution

What is the major product of the following alcohol dehydration?

Watch Solution

DRAW THE MOLECULAR STRUCTURE OF THE FOLLOWING REACTION PRODUCT(S).

Two products, both of molecular formula C10H18, from reaction of 1-(1,1-dimethylethyl)cyclohexanol (1-tert-butylcyclohexanol) with concentrated H2SO4.

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 all answers in skeletal form.

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

What would be the optimal conditions to effect the following transformation? 

A)              Dilute H2SO4

B)              Concentrated H2SO4

C)              Dilute HBr

D)             Concentrated HBr

Watch Solution

Acid-catalyzed dehydration of 3-methyl-2-butanol gives three alkenes: 2-methyl-2-butene, 3-methyl-1- butene, and 2-methyl-1-butene. Propose a mechanism to account for the formation of each product.

Watch Solution

Provide the following when a product is given. If an organic reactant is missing, supply a structural formula; if an inorganic reactant (reagent) or catalyst is missing, simply give a formula. 

Watch Solution

For each of the following, supply a structural formula for the major organic product(s) when the product(s) is/are not given; if no reaction occurs, write N.R. Give the best possible answers. Be sure to show stereoisomers properly when necessary.

Watch Solution

Complete the mechanism for the following acid-catalyzed dehydration of a alcohol reaction. Draw all the arrows to indicate movement of electrons, write all lone pairs, all formal charges, and all the products for each step. In the dotted box write which mechanistic element is involved in each step. If a racemic mixture is formed you must draw both enantiomers by drawing dashes and wedges and write RACEMIC. Draw the expected reaction coordinate diagram for the above reaction. Assume the above reaction is overall exothermic.

Watch Solution

Provide a detailed mechanism for the following transformation using a curved arrow notation.

Watch Solution

Which of the mechanistic steps shown is not a reasonable one in the mechanism to describe the formation of 2-methyl-1-butene by dehydration of 3-methyl-2-butanol?

Watch Solution

What would be the first step in the dehydration of cyclohexanol in sulfuric acid?

a) loss of OH -

b) loss of Hby the alcohol

c) formation of a sulfite ester

d) protonation of the alcohol

Watch Solution

If this alcohol is dehydrated, which alkene is likely to be formed in the largest quantity?

Watch Solution

Why would the concentrated hydrobromic acid be an inappropriate catalyst for the dehydration of alcohols?

a) HBr is too weakly acidic to protonate the alcohol.

b) The conjugate base, Br - , is a good nucleophile and it would attack the carbocation to form an alkyl bromide. 

c) HBr is strongly acidic, so the water molecule would not be a good leaving group after protonation of the alcohol.

d) HBr would be more likely to promote rearrangement of the carbocation intermediate. 

Watch Solution

For the following dehydration:

A. Predict the product of the following reaction.

B. Construct a reaction mechanism that accounts for the product proposed.

C. Construct a reaction coordinate diagram for the reaction. Label all axes. Note that the reaction has three steps: The 1st is fast and endothermic. The 2nd is slow and endothermic. The 3rd is fast and exothermic. The overall reaction is exothermic.

D. Using complete sentences state how you have shown that the 1st and 3rd steps are fast and that the 2nd reaction is slow.

Watch Solution

What is/are the major product(s) of the following reaction? What mechanism does it follow (E1, E2, SN1, or SN2)? (Hint: Note the temperature and reaction time).  

Watch Solution

Predict the organic product(s) of the following reaction. When appropriate, be sure to indicate stereochemistry. Be sure to indicate the major product if more than one product is formed. Draw all answers in skeletal form. 

Watch Solution

Select the product(s) from the following reaction.

Watch Solution

Propose a mechanism for the following reaction

Watch Solution

Draw the mechanism for the following elimination reaction, without a carbocation rearrangement, and in the presence of sulfuric acid, H2SO4, as reagent. Indicate if it follows an E1 or an E2 mechanism.

Watch Solution