Organic Chemistry : Redox Chemistry

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #2 : Using Other Organic Reducing Agents

Which reagents reduce alkynes to trans alkenes?

Possible Answers:

 

Meta-Chloroperoxybenzoic acid 

Correct answer:

Explanation:

 produces a trans-alkene from an alkyne whereas   produces a cis-alkene.  reduces an alkyne all the way down to an alkane.  is a strong oxidizing agent.

Example Question #471 : Organic Chemistry

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Identify the major product of the pictured reaction. Assume workup.

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2. Img 0692

3. Img 0689

4. Img 0690

Possible Answers:

Correct answer:

Explanation:

This is a standard organolithium reaction.

The organolithium product can be thought of as a strong nucleophile. The carbon steals an electron from the lithium to create . From there, the highly reactive carbo-anion is free to attack the ketone at the site of its carbon to form a tertiary alcohol on the cyclohexane.

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Example Question #11 : Organic Reducing Agents

Which of the following compounds is not an oxidizing agent?

Possible Answers:

Correct answer:

Explanation:

 is the only answer choice that is not an oxidizing agent. In fact, it is a reducing agent because of the lack of oxygen atoms present. This compound adds hydrogen atoms to a compound, thereby reducing it.

Example Question #5 : Using Other Organic Reducing Agents

Screen shot 2015 12 29 at 7.06.21 pm

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

Possible Answers:

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Screen shot 2015 12 29 at 7.06.40 pm

Screen shot 2015 12 29 at 7.06.36 pm

Screen shot 2015 12 29 at 7.06.25 pm

Correct answer:

Screen shot 2015 12 29 at 7.06.40 pm

Explanation:

Alkenes can be reduced in the presence of  and a metal catalyst like platinum to hydrogenate the alkene to give a saturated alkane. The reaction occurs in a heterogeneous solution rather than a homogenous solution. It occurs on the presence of a solid surface of the metal catalyst.

Note that the three carbon-carbon double bonds in the aromatic ring in the presence of the reducing agent does not get reduced because they are extremely stable due to resonance.

Example Question #1 : Finding Oxidation Number

The oxidation numbers of calcium and chromium in the compound  are __________ and __________, respectively.

Possible Answers:

Correct answer:

Explanation:

Calcium is in the second group of the periodic table, so its oxidation number will always be . This is true for all alkaline earth metals.

As for chromium, the dichromate anion () has an overall charge of . Each oxygen atom will always have an oxidation number of  as well, so the oxygens would have a total negative charge of . The sum of the oxidation numbers have to equal the overall charge, so chromium must be used to balance the negative charges from the oxygen. To bring the overall charge to , the two chromiums have to have total charge of , giving each an oxidation number of .

Example Question #2 : Oxidation Reduction Reactions

What is the oxidation number of the manganese in potassium permanganate?

Possible Answers:

None of these

Correct answer:

Explanation:

Manganese is a transition metal, so its oxidation number is more variable than the other elements of the compound. Oxygen is almost always . Potassium is almost always . The sum of the oxygens and the potassium is .

The compound is neutral, so the manganese is  to balance the net molecular charge.

Example Question #1 : Oxidation Reduction Reactions

Compared to oxygen in water, the oxygen in hydrogen peroxide has __________ valence electron(s).

Possible Answers:

One less

One more

Two more

The same

Correct answer:

One less

Explanation:

To solve this question we need to calculate the oxidation number of oxygen in both molecules. The formula for water is . The oxidation number of hydrogen is +1. Since there are two of them, the hydrogen atoms contribute to a charge of +2. The water molecule is neutral; therefore, the oxygen must have an oxidation number of  to balance the charge. The formula for hydrogen peroxide is . Using the same logic as water, we can determine that hydrogen contributes +2. We have two oxygen atoms in this case; therefore, each oxygen atom will have an oxidation number of  to give a charge of . This will balance the charges and provide a neutral hydrogen peroxide molecule.

Recall that have a negative charge suggests that an atom has extra valence electrons. A charge of  suggests one extra valence electron and a charge of  suggests two extra valence electrons. An oxygen typically has six valence electrons. The oxygen in water has  oxidation number; therefore, it will have two extra valence electrons (eight total). On the other hand, oxygen in hydrogen peroxide will have one extra valence electron (seven total); therefore, oxygen in hydrogen peroxide has one less valence electron than oxygen in water.

Example Question #1 : Oxidation Reduction Reactions

Which of the following is true regarding the correct oxidation number of potassium in potassium bromide?

Possible Answers:

Correct answer:

Explanation:

Potassium bromide has a formula of . This molecule is made up of an alkali metal (potassium) and a halogen (bromine). Alkali metals have one valence electron that they readily lose to obtain octet whereas halogens have seven valence electrons and they readily gain an electron to obtain octet. Recall that losing an electron will give you a  oxidation number whereas gaining an electron will give you a  oxidation number. This means that alkali metals always have an oxidation number of  whereas halogens always have an oxidation number of ; therefore, potassium has an oxidation number of .

Example Question #1 : Oxidation Reduction Reactions

Which of the following is the correct oxidation number of manganese in Manganese(III) oxide?

Possible Answers:

Correct answer:

Explanation:

Manganese(III) oxide has a formula of . The oxidation number of oxygen is . Since there are three of them, the oxygen atoms contribute to a charge of . To maintain the neutrality of the molecule, manganese must balance the  charge (meaning contribute  charge). There are two manganese atoms; therefore, each manganese atom will have an oxidation number of  and contribute  charge.

Example Question #6 : Oxidation Reduction Reactions

A student reacts sodium chloride and lithium bromide. He collects the products in a jar and performs several tests on them. He concludes that product A has a metal and a nonmetal and that the metal has an oxidation number of  whereas the nonmetal has an oxidation number of . What can you conclude from these results?

Possible Answers:

The other product will have similar oxidation numbers (metal:  and nonmetal: )

The results seem invalid

The identity of product A is sodium bromide

The identity of product A is lithium chloride

Correct answer:

The results seem invalid

Explanation:

The reaction stated in this question is as follows.

This is a double replacement reaction. Both products contain a metal (an alkali metal) and a nonmetal (a halogen). The oxidation number of all alkali metals (first column of periodic table) is  and of all halogens (seventh column of periodic table) is . The results stated in the question seem invalid because a halogen can never have an oxidation number of .

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