Organic Chemistry : Organic Concepts

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #18 : Help With Substitution Reactions

Screen shot 2016 02 22 at 11.02.15 am

Classify the type of reaction given.

Possible Answers:

Substitution

reaction

Heterolytic

Addition

Correct answer:

Substitution

Explanation:

A substitution reaction is a chemical reaction that occurs when the reactants exchange atoms to form new products. In the reaction given the chloride in 1-chloro-4-nitrobenzene  is substituted for the hydroxide in sodium hydroxide to form 4-nitrophenol. Also the hydroxide in sodium hydroxide is substituted for the chloride in 1-chloro-4-nitrobenzene to form sodium chloride.

Example Question #19 : Help With Substitution Reactions

Screen shot 2016 02 21 at 7.20.51 am

Classify the type of reaction given.

Possible Answers:

Substitution

Elimination

Addition

Rearrangement

Correct answer:

Substitution

Explanation:

A substitution reaction is a chemical reaction that occurs when the reactants exchange atoms to form new products. In the reaction given the hydrogen atom in benzene is substituted for the nitro group in nitric acid to form nitrobenzene.

Example Question #20 : Help With Substitution Reactions

What is the product of the reaction shown?


Image8

Possible Answers:

None of these

Correct answer:

Explanation:

The reaction shown is a nucleophilic substitution reaction. The molecule shown is a primary alkyl bromide, and the nucleophile that will be used is the iodide anion (). In this type of reaction the iodide will displace the bromide on the organic molecule, generating iodoethane ().

Example Question #32 : Reactions Types

What is the product of the reaction shown?

Image10

Possible Answers:

Correct answer:

Explanation:

This reaction is an example of a nucleophilic substitution on a secondary alkyl halide. The nucleophile in this case is cyanide (), and the atom that attacks in the cyanide ion is the carbon. Because cyanide is a good nucleophile, the reaction will occur via  mechanism. The answer is thus the molecule where the bromide is replaced with cyanide.

Note: when nucleophilic substitution is performed using a nucleophile that contains carbon (Grignard reagents, acetylide reagents, cyanide, etc.) it is often easy to incorrectly count the number of carbons in the final product.

Example Question #51 : Organic Concepts

Question 8

Which of these molecules would have a faster SN2 reaction?

Possible Answers:

1-iodobutane

They would have the same rate. 

1-bromobutane

Neither would react. 

Correct answer:

1-iodobutane

Explanation:

 is a better leaving group because it is a larger atom and thus has its negative charge spread more evenly. It is more stable and a weaker base than . The molecule with the leaving group that would be most stable, or the weakest base, is the molecule that would react fastest in an SN2 reaction. 

Example Question #22 : Help With Substitution Reactions

Question 10

Which of these would undergo a faster SN2 reaction?

Possible Answers:

1-bromopropane

2-bromobutane

They would react at the same rate. 

Neither would undergo the reaction.

Correct answer:

1-bromopropane

Explanation:

There would be more steric hindrance for a nucleophile in the 2-bromobutane because the leaving group, bromine, is located on a secondary carbon atom. A secondary carbon atom is attached to two other carbon atoms. The leaving group on the 1-propane is located on a primary carbon atom, which is attached to only one other carbon atom. 

Example Question #23 : Help With Substitution Reactions

Question 10

What is the rate law for this equation? 

Possible Answers:

rate = k[Nucleophile][R-Leaving Group]

rate = k[Nucleophile]2

rate = k[R-Leaving Group]

rate = k[R-Leaving Group]2

Correct answer:

rate = k[R-Leaving Group]

Explanation:

This reaction would occur using an SN1 mechanism because the leaving group is attached to a tertiary carbon, a carbon atom with three of the carbon atoms attached to it. The rate laws for SN1 mechanisms do not depend on the nucleophile concentration. The slow-step occurs unimolecularly within the molecule with the leaving group. 

Example Question #1 : Help With Elimination Reactions

Which of the following reaction conditions favors an E1 reaction mechanism?

Possible Answers:

Aprotic solvent

Weak base

Strong base

Weak nucleophile

Strong nucleophile

Correct answer:

Weak base

Explanation:

E1 reactions occur in two steps. First, the leaving group is removed, yielding a carbocation. Second, a weak base removes a proton from the carbon adjacent to the carbocation carbon. Thus, to favor E1, a protic solvent is desired in order to stabilize the carbocation. Weak bases favor an E1 mechanism.

Example Question #55 : Organic Concepts

Which of the following conditions favors an E2 mechanism?

Possible Answers:

Strong nucleophile

Weak nucleophile

Weak base

Strong base

Strong electrophile

Correct answer:

Strong base

Explanation:

E2 reaction occur in only one step. The strong base removes the beta-hydrogen, while the leaving group simultaneously leaves. The double bond forms simultaneously. 

Example Question #2 : Help With Elimination Reactions

In an elimination reaction __________.

Possible Answers:

one sigma bond and one pi bond are broken, and two sigma bonds are formed

one pi bond is broken and one pi bond is formed

two pi bonds are broken and one sigma bond is formed

two sigma bonds are broken, and one sigma and one pi bond are formed

one sigma bond is broken and one sigma bond is formed

Correct answer:

two sigma bonds are broken, and one sigma and one pi bond are formed

Explanation:

Elimination reactions involve the use of bases, which remove hydrogen atoms. The leaving group, which is bound via a sigma bond is removed, along with a hydrogen (thus two sigma bonds are broken). The result is a double bond, which consists of one sigma bond and one pi bond. 

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