Organic Chemistry : Nucleophiles and Electrophiles

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #11 : Identifying Nucleophiles

Which of the following is the worst nucleophile?

Possible Answers:

Correct answer:

Explanation:

 is least nucleophilic because its oxygen has no negative charge, and oxygen is more electronegative than sulfur, thus the lone pair of electrons on oxygen are more stable than they would be on sulfur or nitrogen.

Example Question #12 : Nucleophiles And Electrophiles

Which of the following sentences correctly explains why iodide () is a better nucleophile than fluoride () in a polar protic solvent?

Possible Answers:

is more electronegative than  which causes  to interact more with the solvent (the more abundant substance) than with the target molecule.

 is more electronegative than  which causes  to interact more with the target molecule than with the solvent (the more abundant molecule).

 is less electronegative than  which causes  to interact more with the solvent (the more abundant substance) than with the target molecule.

 is less electronegative than  which causes  to interact more with the target molecule than with the solvent (the more abundant molecule).

None of the other answers.

Correct answer:

is more electronegative than  which causes  to interact more with the solvent (the more abundant substance) than with the target molecule.

Explanation:

 forms strong hydrogen bonds with polar protic solvents, which makes it less able to interact with any target molecules (electrophiles). Note: in a polar aprotic solvent, hydrogen bonds cannot form, and  is more nucleophilic than .

Example Question #13 : Nucleophiles And Electrophiles

Which of the following compounds can be considered a Lewis base?

Possible Answers:

Correct answer:

Explanation:

A Lewis base is a compound that donates a pair of electrons. The only compound shown that possesses an electron pair that can be donated is ammonia.  is the Lewis base.  and  are Lewis acids and are therefore wrong. Neither carbon dioxide nor methane are Lewis bases.

Example Question #11 : Nucleophiles And Electrophiles

Which of these qualities applies to a good nucleophile?

Possible Answers:

Wants to accept electrons

More bulky

Is a conjugate acid

Less bulky

Correct answer:

Less bulky

Explanation:

A good nucleophile should not be bulky. If the nucleophile is bulky, the compound will not be able to reach the carbonyl carbon, where the reaction occurs. With increased steric hindrance due to a bulkier nucleophile, the reaction will run slowly, and the compound is not a good nucleophile. Good nucleophiles also want to give away electrons so that the reaction can occur. This means that conjugate bases make better nucleophiles than acids.

Example Question #13 : Identifying Nucleophiles

Which of the following is least likely to result in substitution when added to a secondary halide.

Possible Answers:

Correct answer:

Explanation:

To promote elimination rather than substitution, a molecule must be a strong base and weakly nucleophilic. Typically weak nucleophiles are large and bulky, which therefore have difficulty undergoing backside attack. Only tert-butoxide is a weak nucleophile, due to its branching, meaning it is least likely to participate in substitution. 

Example Question #14 : Identifying Nucleophiles

Which of the following is the best leaving group?

Possible Answers:

Correct answer:

Explanation:

 is the weakest base as its negative charge is spread out more evenly over the large atom. Thus, it is the best leaving group of these four halogens. It is the best leaving group due to its largest size and distribution of negative charge. 

Example Question #1 : Identifying Electrophiles

The molecule pictured is known as rapamycin, or Sirolimus, and is used as an immunosuppressant during organ transplants. Which of the following colored carbonyl groups is the most electrophilic?


        Q7

Possible Answers:

Purple

Blue

Gold

Red

Green

Correct answer:

Gold

Explanation:

Note that many of these carbonyl groups are actually part of various functional groups. For example, the gold is an aldehyde, the green and purple are both ketones, the red is an amide, and the blue is an ester. We know the electrophilicity of carbonyl-containing functional groups is as follows:

 

A7 

Thus, our aldehyde, in gold, is the most electrophilic.

Example Question #1 : Identifying Electrophiles

Which compound is not a Lewis acid?

Possible Answers:

All of the given compounds are Lewis acids

Correct answer:

Explanation:

A Lewis acid is an electron pair acceptor. A Lewis base is an electron pair donor.

 is an ionic molecule and is neutral.  and  have positive charges and are electron pair acceptors, as they are more stable when they are neutral.

The correct answer, , has a lone pair on the nitrogen atom that can be donated to form bonds with other atoms, so it is a Lewis base.

Example Question #11 : Nucleophiles And Electrophiles

Which of these is a typical electrophile?

Possible Answers:

Ammonia

Chloride ion

Iodide ion

Methyl carbocation

Correct answer:

Methyl carbocation

Explanation:

Electrophiles are substances that accept an electron pair to form a covalent bond, and nucleophiles are those that donate an electron pair to form a covalent bond. The chloride and iodide ions are both nucleophiles, as they each have a charge of  and would thus be willing to donate their extra electron. Ammonia () is also a nucleophile, as the nitrogen has a lone pair of electrons to donate. The methyl carbocation (carbon attached to three hydrogen atoms, with a positive charge) is an electrophile. The positive charge on the carbon makes it willing to accept an electron pair to form a covalent bond.

Example Question #92 : Organic Chemistry

Electron donation and withdrawal have important impacts on acidity. What R group would yield the species with the highest pKa?

 Q5

Possible Answers:

Correct answer:

Explanation:

This question tests your knowledge about electron donation, as well as acidity. The question asks you to identify the species with the highest pKa, which means you need to look for the R group that will be the most donating. Electron donation will destabilize the conjugate base anion, localized partially on the oxygen of the hydroxyl moiety; the result is a less acidic acid, and a higher pKa.

Of the answer choices, three are electron-withdrawing. These include the nitro (-NO2), the ketone (-CCOMe), and the carboxyl (-COOH). The only answer choices that are electron-donating are the methyl (-Me), and the ether (-OMe). As the ether can push its lone pairs into the pi system of the ring and the carboxyl group, it is the stronger electron-donating group. The methyl can only donate electrons through inductive effects, or electronic polarization of sigma bonds, which is not as strong of an electron donation effect. Thus, -OMe is the correct answer.

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