Organic Chemistry : Reactions by Reactant

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #5 : Help With Alkene Reactions

Which of the following show the major product of the addition of hydrobromic acid to 2-methylhex-2-ene?

Possible Answers:

Noname03

Noname05

Noname06

Noname02

Noname04

Correct answer:

Noname06

Explanation:

This is an addition reaction with  being added to an alkene (ionic addition). To reach the correct answer first we need to add the  to one of the carbons by using electrons from the double bond. This next step is crucial because the positive charge (carbocation) that forms needs to be in the most substituted position. However, hydride shifts can occur moving a hydrogen atom over to an adjacent carbon to form the most stable carbocation. In this case, the positive charge on the secondary carbon adjacent to the tertiary carbon will first get the positive charge and then a hydride shift will occur amongst those two carbon leading to a more stable tertiary carbocation. Finally, the  will attack the carbocation from both sides, and then we will have an alkyl halide. The most stable intermediate (carbocation) produces the greatest quantity of the stable product. 

Example Question #1 : Help With Alkene Reactions

When reacted with 1 equivalent of , which of these molecules could form multiple products?

Screen shot 2015 10 24 at 10.11.48 am

Possible Answers:

2 and 4

1 and 4

1 and 3

1, 4 and 5

2, 3 and 4

Correct answer:

2, 3 and 4

Explanation:

This is a classic acid catalyzed alkene reaction. Because of resonance, several reactions have multiple products.

Screen shot 2015 10 24 at 10.11.30 am

Example Question #2 : Help With Alkene Reactions

Which of these alkene compounds would react with hydrobromic acid  the fastest?

Possible Answers:

1-Pentene

1-Butene

2-Butene

Ethene

2-Methyl-2-butene

Correct answer:

2-Methyl-2-butene

Explanation:

2-Methyl-2-butene will react the fastest with hydrobromic acid because when it reacts, it will form the most stable carbocation among all of the alkenes listed. This stability allows for the reaction to proceed much quicker than other compounds, therefore it will react the fastest.

Example Question #11 : Help With Alkene Reactions

The ozonolysis reaction involves the use of  (ozone gas) with alkene molecules. This reaction forms which of the following products?

Possible Answers:

Ethers

Carboxylic acids

Terpenes

Esters

Aldehydes

Correct answer:

Aldehydes

Explanation:

The ozonolysis of alkenes forms either ketones or aldehydes. Subsequent reagents can be added to produces alcohols and/or carboxylic acids. 

Example Question #11 : Help With Alkene Reactions

Screen shot 2015 12 20 at 10.37.19 pm

Which of the following is an intermediate in the hydration of ethylene for the reaction given?

Possible Answers:

Screen shot 2015 12 20 at 10.49.28 pm

Screen shot 2015 12 20 at 10.49.34 pm

Screen shot 2015 12 20 at 10.49.07 pm

Screen shot 2015 12 20 at 10.49.13 pm

Correct answer:

Screen shot 2015 12 20 at 10.49.07 pm

Explanation:

The reaction mechanism goes through a carbocation intermediate as follows:

 

Screen shot 2015 12 20 at 11.09.02 pm

 

Therefore the answer is the following carbocation intermediate:

Screen shot 2015 12 20 at 10.49.07 pm

Example Question #12 : Help With Alkene Reactions

Which of the followinng sets of addition reactions proceed via syn addition? 

Possible Answers:

Halohydrin addition, bromination

Bromination, catalytic hydrogenation

Halohydrin addition, epoxidation

Bromination, epoxidation

Hydroboration-oxidation, epoxidation

Correct answer:

Hydroboration-oxidation, epoxidation

Explanation:

Reactions that proceed by syn addition include hydrogenation, epoxidation, and hydroboration-oxidation. Reactions that proceed by anti addition include halogenation, halohydrin addition and epoxidation followed by ring opening. Syn addition occurs because reagents must approach from only one side of the double bond. 

Example Question #11 : Help With Alkene Reactions

Screen shot 2015 12 17 at 10.46.32 pm

Predict the product of the chemical reaction given.

Possible Answers:

Screen shot 2015 12 17 at 10.47.24 pm

Screen shot 2015 12 17 at 10.49.50 pm

Screen shot 2015 12 17 at 10.50.48 pm

Screen shot 2015 12 17 at 10.48.49 pm

Correct answer:

Screen shot 2015 12 17 at 10.47.24 pm

Explanation:

The reaction given is called a Markovnikov's addition reaction. This is a regiospecific reaction because only one orientation of the reaction occurs. It is an electrophilic addition reaction that involves the reaction of a halogenic acid such as  or  with an alkene. The hydrogen bonds to the carbon with the less alkyl groups bonded to the organic compound and the halogen ion bonds to the carbon with more alkyl substituents. Therefore the answer is:Screen shot 2015 12 17 at 10.47.24 pm

Example Question #15 : Help With Alkene Reactions

Screen shot 2015 12 17 at 11.23.40 pm

Predict the product of the chemical reaction given.

Possible Answers:

Screen shot 2015 12 17 at 11.23.48 pm

Screen shot 2015 12 17 at 11.23.53 pm

Screen shot 2015 12 17 at 11.24.07 pm

Screen shot 2015 12 17 at 11.24.02 pm

Correct answer:

Screen shot 2015 12 17 at 11.23.48 pm

Explanation:

The reaction given is called a Markovnikov's addition reaction. This is a regiospecific reaction because only one orientation of the reaction occurs. It is an electrophilic addition reaction that involves the reaction of a halogenic acid such as  or  with an alkene. The hydrogen bonds to the carbon with the less alkyl groups bonded to the organic compound and the halogen ion bonds to the carbon with more alkyl substituents. Therefore the answer is:Screen shot 2015 12 17 at 11.23.48 pm

Example Question #11 : Reactions By Reactant

Screen shot 2015 12 29 at 7.56.05 pm

Which of the following would be the product of the reaction given?

Possible Answers:

Screen shot 2015 12 29 at 7.56.42 pm

Screen shot 2015 12 29 at 7.56.31 pm

Screen shot 2015 12 29 at 7.56.26 pm

Screen shot 2015 12 29 at 7.56.49 pm

Correct answer:

Screen shot 2015 12 29 at 7.56.26 pm

Explanation:

Molecular chlorine reacts with an alkene in the presence of water to yield a halohydrin product. Below is the mechanism for this reaction:

Screen shot 2015 12 29 at 7.56.58 pm

Example Question #11 : Reactions By Reactant

Screen shot 2015 12 29 at 8.22.26 pm

Which of the following would be the product of the reaction given?

Possible Answers:

Screen shot 2015 12 29 at 8.23.30 pm

Screen shot 2015 12 29 at 8.23.25 pm

Screen shot 2015 12 29 at 8.23.34 pm

Screen shot 2015 12 29 at 8.26.49 pm

Correct answer:

Screen shot 2015 12 29 at 8.23.25 pm

Explanation:

Molecular bromine reacts with an alkene in the presence of water to yield a halohydrin product. Below is the mechanism for this reaction:

Screen shot 2015 12 29 at 8.23.16 pm

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