Organic Chemistry : Redox Chemistry

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #3 : Using Sodium Borohydride

Which of the following statements is false?

Possible Answers:

 can be used to reduce an acid halide into a primary alcohol

 can be used to reduce a ketone into a secondary alcohol

 can be used to reduce an aldehyde into a primary alcohol

None of these

Correct answer:

None of these

Explanation:

These are all true uses of .

Example Question #1 : Organic Reducing Agents

What is the product of the reaction between magnesium and any alkyl halide, in anhydrous ether?

Possible Answers:

An alkane

An alcohol

An aldehyde

A Grignard reagent

An organolithium

Correct answer:

A Grignard reagent

Explanation:

The reaction between magnesium and an alkyl halide in anhydrous ether results in a Grignard reagent.

An organolithium would result from the same process, but the magnesium would need to be replaced by two equivalents of lithium. Alcohols are products of reactions between a Grignard reagent and a carbonyl. 

Example Question #1 : Using Grignard Reagents

What type of reaction would ensue if the ketone compound shown was introduced to  (a Grignard reagent in water).

Possible Answers:

Oxidation-reduction reaction

Grignard addition reaction

No reaction

Correct answer:

No reaction

Explanation:

Grignard reagents are known for their ability to readily attack carbonyls at the point of their carbons. However, Grignard reagents do not work in the presence of protic solvents. Rather than reacting with the desired molecule, the Grignard is so unstable that it will readily accept a proton from a protic solvent. The Grignard then becomes inert and no reaction ensues with the desired molecule.

Example Question #1 : Using Grignard Reagents

3-bromopropene was treated with 

What is the final major product?

Possible Answers:

Hexanol

Cyclohexene

6-bromohex-4-ene

Hexene

Correct answer:

Hexene

Explanation:

Any time we have a Grignard reagent and a primary haloalkane, we will see a substitution reaction, identical to an  reaction. In this case, the Grignard can easily attack the haloalkane as the bromine leaves to create hexene.

Example Question #4 : Using Grignard Reagents

Img 0711

What reactant(s) is/are needed to drive this reaction?

Possible Answers:

Correct answer:

Explanation:

The carbons on the epoxide compound experience a slightly positive charge. As a result, a Gringard reagent can easily attack the less substituted side of the epoxide to break the ring and to form a six membered carbon chain.  is used to protonate the negatively charged oxygen atom.

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Example Question #1 : Using Lithium Aluminum Hydride

Which of the following can be reduced when mixed with ?

Possible Answers:

Correct answer:

Explanation:

 is a very powerful reducing agent that works to reduce almost any carbonyl compound.  is an amide and the only carbonyl compound given of the answer choices.

Example Question #1 : Using Lithium Aluminum Hydride

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What reagents are needed to satisfy the given reaction?

Possible Answers:

Correct answer:

Explanation:

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This problem requires that we convert our ketone group into a chlorine. However, this cannot be done directly, and requires multiple steps.

We begin by reducing the ketone with  to form an alcoxide. The alcoxide undergoes workup (the process whereby a negatively charged oxygen gains a proton) via , depicted above as simply "". We now have a secondary alcohol. From here, we can simply use the reagent  to convert the alcohol into the desired chlorine.

Example Question #21 : Redox Chemistry

What is the product of the given reaction? 

Screen shot 2015 11 13 at 3.38.24 pm

Screen shot 2015 11 13 at 3.39.24 pm

Possible Answers:

III

IV

V

I

II

Correct answer:

IV

Explanation:

First step: esterification

Second step: lithium aluminum hydride reduction

Third step: neutralization to form primary alcohol

Fourth step: SN2 reaction to form final chlorinated product

Example Question #22 : Redox Chemistry

What is the result of the following reaction?

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Possible Answers:

All of the above

Correct answer:

Explanation:

Lithium Aluminum Hydride is a potent reducing agent; it has the ability to turn esters and aldehydes into primary alcohols, and ketones into secondary alcohols. The starting material is an aldehyde, so the correct answer is thus a primary alcohol ONLY.

Example Question #23 : Redox Chemistry

Which of the following is not a reducing agent?

Possible Answers:

Correct answer:

Explanation:

 is not a reducing agent; peroxides (compounds with the formula R-O-O-R) are oxidizing agents. A very common peroxide is sodium peroxide .

All of the other listed compounds are reducing agents.

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