Organic Chemistry : Organic Chemistry

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #521 : Organic Chemistry

How many stable resonance structures are there for the following molecule (include the given structure in your total count)?

Screen shot 2015 10 24 at 10.14.54 am

Possible Answers:

5

1

6

3

4

Correct answer:

5

Explanation:

The five resonance structures of the given molecule are shown below:

Screen shot 2015 10 24 at 10.15.07 am

Example Question #3 : Other Reaction Mechanisms

Rank the following compounds in order of increasing rate of electrophilic aromatic substitution.

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Possible Answers:

V, II, I, III, IV

V, I, III, IV, II

II, I, III, IV, V

IV, V, I, III, II

II, IV, III, I, V

Correct answer:

V, I, III, IV, II

Explanation:

The nitro substituent is strongly deactivating, ketones are moderately deactivating substituent, halides are weakly deactivating, alkyl groups are weakly activating, and amine groups are strongly activating.

Example Question #1 : Other Reaction Mechanisms

Which of these would react fastest with methanol via an SN1 mechanism?

Possible Answers:

All of these will react with similar rates when undergoing an SN1 reaction with methanol

Correct answer:

Explanation:

An SN1 mechanism involves the leaving of the bromine in the first step and the formation of a carbocation on that carbon. The molecule with the most stable carbocation will react most quickly.

The carbocation is most stable on the most highly substituted carbon. All the of the answer options form primary or secondary cations except for one. The correct answer has a carbocation on a carbon bonded to two methyl groups and one ethyl group. The correct answer is .

Example Question #1 : Other Reaction Mechanisms


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What is the major product of the reaction shown above?

Possible Answers:

Img 20150723 140255

Img 20150723 140319

Img 20150723 140248

Img 20150723 140303

Correct answer:

Img 20150723 140248

Explanation:

Grignard reagents attack ketones at the site of the ketone's carbon to produce tertiary alcohols.

Example Question #1 : Identifying Reaction Mechanisms

Under which of the following sets of conditions is an SN2 reaction most favored?

Possible Answers:

Acetone solvent, tertiary electrophile, strong nucleophile

Methanol solvent, tertiary electrophile, weak nucleophile

DMSO solvent, primary electrophile, weak nucleophile

Ethanol solvent, primary electrophile, strong nucleophile

Ether solvent, primary electrophile, strong nucleophile

Correct answer:

Ether solvent, primary electrophile, strong nucleophile

Explanation:

SN2 reactions require a strong nucleophile. If the the nucleophile is weak, SN1 is favored over SN2.

For SN2 reactions less substitution in the electrophile is favored (methyl > primary > secondary).

For SN2 reactions polar aprotic solvents are preferred (DMSO, acetone, DMF and ethers are common polar aprotic solvents). Polar protic solvents (ethanol, methanol) favor SN1 reactions.

Example Question #7 : Other Reaction Mechanisms

Consider the generic reaction shown below.

What type of reaction is occurring here?

Possible Answers:

Elimination

Rearrangement

Addition

Substitution

Correct answer:

Substitution

Explanation:

In this question, we're presented with a hypothetical reaction, and we're asked to identify which type of reaction is occurring. Let's go through each of the answer choices to see which one fits.

Addition reactions are ones in which two atoms or molecules come together. It takes the form of .

Elimination reactions are essentially the opposite of addition reactions. In this case, a molecule splits into two, taking the form of .

Rearrangement reactions are ones in which the reactant is manipulated in a way that gives product, but in the process, no additional reactants are consumed and no additional products are made. It takes the general form of .

Substitution reactions are ones in which there is some sort of exchange of atoms or functional groups between different reactants to give new products. In the reaction shown in the question stem, this qualifies as a substitution reaction.

Example Question #1 : Reaction Energetics And Kinetmatics

With what mechanism do catalysts speed up a reaction?

Possible Answers:

They lower the  of the reaction.

They raise the activation energy of the reaction.

They lower the activation energy of the reaction.

They increase the  of the reaction.

Correct answer:

They lower the activation energy of the reaction.

Explanation:

Regarding chemical reactions, the activation energy is the minimum energy which must be available in a chemical system in order for reactants to participate in a chemical reaction. Catalysts speed up reactions by lowering this minimum energy. Raising it would have the opposite effect. Catalysts do not alter the  of a reaction. Remember this--it is a common error to make!

Example Question #1 : Reaction Energetics And Kinetmatics

What kinetic equation describes the rate of an E1 process?

Possible Answers:

None of these

Correct answer:

Explanation:

Most organic reactions are carried out in multiple steps. The rate equation can be derived from the process that occurs in the slowest step of the mechanism. An E1 reaction's slow step is when a leaving group separates from the hydrocarbon and a carbocation is formed. The only reactant in this step is one molar equivalent of the hydrocarbon. Thus, the rate equation only depends on that substance. The molar equivalent determines the exponent of each reactant in the equation.

Example Question #1 : Reaction Energetics And Kinetmatics

Generally, when compared to the rate of inorganic reactions, the rate of organic reactions is __________.

Possible Answers:

Faster, because organic compounds contain covalent compounds

Slower, because organic compounds contain covalent bonds

Slower, because organic compounds are ionic

Faster, because organic compounds are ionic

Correct answer:

Slower, because organic compounds contain covalent bonds

Explanation:

By and large, organic compounds contain mainly covalent bonds. Covalent bonds are typically harder to break, which is why organic reactions happen at a relatively slower rate than inorganic reactions.

Example Question #1 : Hydrocarbons

Which of the following can reduce an alkene to an alkane?

Possible Answers:

Lithium aluminum hydride (LiAlH4) and H2/Pd

H2/Pd and H2/Raney nickel

H2/Pd

Lithium aluminum hydride (LiAlH4)

H2/Raney nickel

Correct answer:

H2/Pd and H2/Raney nickel

Explanation:

Neither lithium aluminum hydride, nor sodium borohydride will reduce C–C double bonds.

H2/Raney nickel and H2/Pd can each (individually) reduce an alkene to an alkane. Since both H2/Raney nickel and H2/Pd can reduce the alkene, the answer is both of those reagents. This is a catalytic hydrogenation reaction, and H2/Raney nickel not only reduces C–C double bonds, but also carbonyl compounds.

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