Addition Reactions of AlkenesAlkynesOrganic Synthesis ProblemsReactions of Alcohols

Organic (Orgo) 1 Synthesis Practice Problems

The main Organic Chemistry 1 chapters in most US curricula go up to the reactions of alcohols. So, this summary will include synthesis practice problems on Alkenes, Alkynes, and Alcohols. If you need to practice SN1, SN2, E1, and E2 substitution and elimination reactions, refer to the following posts.

With that said, the ones covering the reactions of alkenes, alkynes, and alcohols are not one-step conversions, as that is not synthesis as such. For the conversions of these functional groups, refer to the corresponding article on the Topics page, the Study Guide available here, as well as the Reaction Maps, which are definitely going to help you solve the synthesis problems as well. So, have them available on a separate tab.

 

Organic Chemistry Reaction Maps

 

 

Practice

1.

Identify the reagents for each of the following addition reactions to an alkene:

Answer

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2.

Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:

Answer

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Solution

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3.

Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:

Answer

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Solution

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4.

Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compounds A and B:

Answer

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5.

Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:

Answer

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6.

Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:

Answer

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7.

Predict the product(s) that are formed after each step for reactions A-G. In each case, consider formation of any chiral center(s) and draw all expected stereoisomers.

 

This is a comprehensive problem that covers the following topics and will serve as a review of all of them:

Substitution and elimination reactions. Particularly, substitution and elimination reactions of alcohols, the regio– and stereochemistry of E2 reactions and E2 reaction of cyclohexanes.

Mesylation and tosylation in Substitution and elimination reactions. 

Hydrohalogenation of alkenes according to the Markovnikov’s rule.

Radical hydrohalogenation of alkenes.

Hydroboration-Oxidation of Alkenes.

Halogenation of alkenes through halohydrin formation.

Syn and anti dihydroxilation of alkenes.

Elimination reactions: Zaitsev and Hoffman products.

Ozonoloysis of Alkenes.

Attempt solving the entire problem before accessing the answers!

The answers will give you the structure of the final product(s) only. Use this as a hint to determine the compounds formed after the first and second reactions.

The structure of intermediate compounds can be found under the Solution tab.

a)
Answer

b)
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c)
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d)
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e)
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f)
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g)
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Solution

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8.

The full Video solution to the problems:

Solution

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9.

Draw a mechanism for each reaction to explain the difference when the following alkenes are reacted with bromine.

Hint: drawing the chair conformations will be very helpful.

Answer

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10.

Draw a mechanism for the following transformations.

a)
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b)
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11.

Propose a mechanism for the following synthesis:

Answer

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12.

When the following cyclohexenes are brominated different configurational isomers are obtained. How would you explain the stereochemistry of these reactions?

 

Note: Tetraethylammonium bromide (Et4NBr) is a source of Br– ion.

Answer

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13.

Propose a mechanism for the following synthesis:

Answer

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14.

Identify the reagents for each of the following reactions of internal and terminal alkynes:

Answer

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15.

On the following synthetic scheme, identify the reagents, in the correct order, that you would use to achieve the following synthetic transformations. Determine the structure of compounds A and B and the major organic products resulting from the alkyne.

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Solution

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16.

Suggest reagents for the following synthetic transformations of alkenes and alkynes:

 

a)
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b)
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c)
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d)
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17.

Use no other source of carbon to achieve the following synthetic transformations:

 

a)
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b)
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18.

Add the reagents, in the correct order, to achieve an efficient synthesis for each of the following multistep transformations.

a)
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b)
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c)
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d)
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e)
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f)
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Solution

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19.

Identify the missing reagents and products in the following synthetic scheme:

Answer

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20.

Identify the missing reagents and products in the following synthetic scheme:

 

Answer

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21.

Identify the missing reagents and products in the following synthetic scheme:

Answer

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22.

Bonus Question! Which fish is going to click?

 

 

Answer

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23.

Check the related articles on the Topics Page or in the Sidebar menu.

 

Additional practice problems are available in the multiple-choice quizzes.

 

 

 

 

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