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 \(\displaystyle (MCPBA)\)

\(\displaystyle H_{2}/Pd/C\)

\(\displaystyle H_{2}/Lindlar's\) \(\displaystyle Catalyst\)

\(\displaystyle Na/NH_{3}\)

Correct answer:

\(\displaystyle Na/NH_{3}\)

Explanation:

\(\displaystyle Na/NH_{3}\) produces a trans-alkene from an alkyne whereas \(\displaystyle H_{2}/Lindlar's\) \(\displaystyle Catalyst\) produces a cis-alkene. \(\displaystyle H_{2}/Pd/C\) reduces an alkyne all the way down to an alkane. \(\displaystyle MCPBA\) is a strong oxidizing agent.

Example Question #11 : Organic Reducing Agents

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

1. Img 0691

2. Img 0692

3. Img 0689

4. Img 0690

Possible Answers:

\(\displaystyle 1\)

\(\displaystyle 4\)

\(\displaystyle 2\)

\(\displaystyle 3\)

Correct answer:

\(\displaystyle 3\)

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 \(\displaystyle H_{3}C^{-}Li^{+}\). 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.

Img 0693

Example Question #2 : Using Other Organic Reducing Agents

Which of the following compounds is not an oxidizing agent?

Possible Answers:

\(\displaystyle H_{2}CrO_{4}\)

\(\displaystyle O_{3}\)

\(\displaystyle NaBH_{4}\)

\(\displaystyle H_{2}SO_{4}\)

\(\displaystyle KMnO_{4}\)

Correct answer:

\(\displaystyle NaBH_{4}\)

Explanation:

\(\displaystyle NaBH_{4}\) 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 #17 : 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:

Screen shot 2015 12 29 at 7.06.40 pm

Screen shot 2015 12 29 at 7.06.25 pm

Screen shot 2015 12 29 at 7.06.36 pm

Screen shot 2015 12 29 at 7.06.29 pm

Correct answer:

Screen shot 2015 12 29 at 7.06.40 pm

Explanation:

Alkenes can be reduced in the presence of \(\displaystyle H_2\) 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 #31 : Redox Chemistry

The oxidation numbers of calcium and chromium in the compound \(\displaystyle CaCr_2O_7\) are __________ and __________, respectively.

Possible Answers:

\(\displaystyle +2\ .\ .\ .+6\)

\(\displaystyle +1\ .\ .\ .-2\)

\(\displaystyle +1\ .\ .\ .+6\)

\(\displaystyle +2\ .\ .\ .+3\)

\(\displaystyle +2\ .\ .\ .-6\)

Correct answer:

\(\displaystyle +2\ .\ .\ .+6\)

Explanation:

Calcium is in the second group of the periodic table, so its oxidation number will always be \(\displaystyle +2\). This is true for all alkaline earth metals.

As for chromium, the dichromate anion (\(\displaystyle Cr_2O_7^{-2}\)) has an overall charge of \(\displaystyle -2\). Each oxygen atom will always have an oxidation number of \(\displaystyle -2\) as well, so the oxygens would have a total negative charge of \(\displaystyle -14\). 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 \(\displaystyle -2\), the two chromiums have to have total charge of \(\displaystyle +12\), giving each an oxidation number of \(\displaystyle +6\).

Example Question #2 : Oxidation Reduction Reactions

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

Possible Answers:

\(\displaystyle +7\)

\(\displaystyle +4\)

\(\displaystyle -2\)

\(\displaystyle 0\)

None of these

Correct answer:

\(\displaystyle +7\)

Explanation:

Manganese is a transition metal, so its oxidation number is more variable than the other elements of the compound. Oxygen is almost always \(\displaystyle -2\). Potassium is almost always \(\displaystyle +1\). The sum of the oxygens and the potassium is \(\displaystyle -7\).

\(\displaystyle KMnO_4\)

\(\displaystyle K+Mn+4(O)=0\)

\(\displaystyle 1+Mn+4(-2)=-7+Mn=0\)

The compound is neutral, so the manganese is \(\displaystyle +7\) to balance the net molecular charge.

Example Question #3 : Oxidation Reduction Reactions

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

Possible Answers:

Two more

One less

The same

One more

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 \(\displaystyle H_2O\). 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 \(\displaystyle -2\) to balance the charge. The formula for hydrogen peroxide is \(\displaystyle H_2O_2\). 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 \(\displaystyle -1\) to give a charge of \(\displaystyle -2\). 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 \(\displaystyle -1\) suggests one extra valence electron and a charge of \(\displaystyle -2\) suggests two extra valence electrons. An oxygen typically has six valence electrons. The oxygen in water has \(\displaystyle -2\) 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 #4 : Finding Oxidation Number

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

Possible Answers:

\(\displaystyle -2\)

\(\displaystyle -1\)

\(\displaystyle +2\)

\(\displaystyle +1\)

Correct answer:

\(\displaystyle +1\)

Explanation:

Potassium bromide has a formula of \(\displaystyle KBr\). 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 \(\displaystyle +1\) oxidation number whereas gaining an electron will give you a \(\displaystyle -1\) oxidation number. This means that alkali metals always have an oxidation number of \(\displaystyle +1\) whereas halogens always have an oxidation number of \(\displaystyle -1\); therefore, potassium has an oxidation number of \(\displaystyle +1\).

Example Question #5 : Finding Oxidation Number

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

Possible Answers:

\(\displaystyle +4\)

\(\displaystyle +5\)

\(\displaystyle +2\)

\(\displaystyle +3\)

Correct answer:

\(\displaystyle +3\)

Explanation:

Manganese(III) oxide has a formula of \(\displaystyle Mn_2O_3\). The oxidation number of oxygen is \(\displaystyle -2\). Since there are three of them, the oxygen atoms contribute to a charge of \(\displaystyle -6\). To maintain the neutrality of the molecule, manganese must balance the \(\displaystyle -6\) charge (meaning contribute \(\displaystyle +6\) charge). There are two manganese atoms; therefore, each manganese atom will have an oxidation number of \(\displaystyle +3\) and contribute \(\displaystyle +6\) charge.

Example Question #6 : Finding Oxidation Number

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 \(\displaystyle +1\) whereas the nonmetal has an oxidation number of \(\displaystyle -2\). What can you conclude from these results?

Possible Answers:

The identity of product A is lithium chloride

The identity of product A is sodium bromide

The other product will have similar oxidation numbers (metal: \(\displaystyle +1\) and nonmetal: \(\displaystyle -2\))

The results seem invalid

Correct answer:

The results seem invalid

Explanation:

The reaction stated in this question is as follows.

\(\displaystyle NaCl\: + \: LiBr \rightarrow NaBr\: + LiCl\)

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 \(\displaystyle +1\) and of all halogens (seventh column of periodic table) is \(\displaystyle -1\). The results stated in the question seem invalid because a halogen can never have an oxidation number of \(\displaystyle -2\).

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