Reactions by Product - Organic Chemistry
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What is the product when the given starting compound is reacted with lithium aluminum hydride and acid?

What is the product when the given starting compound is reacted with lithium aluminum hydride and acid?
This reaction involves a very strong reducing agent in lithium aluminum hydride,
. LAH converts ketones, aldehydes, esters, and acid chlorides into alcohols. This reaction changes the carbonyl group into a hydroxyl group. As a result, the final answer is 2-butanol.
This reaction involves a very strong reducing agent in lithium aluminum hydride, . LAH converts ketones, aldehydes, esters, and acid chlorides into alcohols. This reaction changes the carbonyl group into a hydroxyl group. As a result, the final answer is 2-butanol.
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What reagents are required to efficiently form a tertiary alcohol with two of the same substituents in only two steps?
What reagents are required to efficiently form a tertiary alcohol with two of the same substituents in only two steps?
This is an example of a Grignard reaction that requires the use of an ester or acid chloride, and more than one equivalent of an organometallic. The second step would be to react the product of the first step in an acidic source.
This is an example of a Grignard reaction that requires the use of an ester or acid chloride, and more than one equivalent of an organometallic. The second step would be to react the product of the first step in an acidic source.
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What is the product of a hydroboration–oxidation reaction with 1-hexylcyclohexene?
What is the product of a hydroboration–oxidation reaction with 1-hexylcyclohexene?
This reaction is an electrophilic addition reaction with an alkene. This is one of many alkene addition reactions that can add an -OH group onto your starting material. The key aspect of an hydroboration-oxidation reaction is the anti-Markovinikov addition to the double bond. The -OH group should be on the least substituted of the two carbons that originate from the double bond. In light of this information, the answer is 2-cyclohexanol.
This reaction is an electrophilic addition reaction with an alkene. This is one of many alkene addition reactions that can add an -OH group onto your starting material. The key aspect of an hydroboration-oxidation reaction is the anti-Markovinikov addition to the double bond. The -OH group should be on the least substituted of the two carbons that originate from the double bond. In light of this information, the answer is 2-cyclohexanol.
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What is the IUPAC name of the given diene?

What is the IUPAC name of the given diene?
You must begin counting the carbons so that the first functional substituent has the lowest possible number. In this case, C1 is connected to C2 by the double bond, meaning we start counting from the left.
The longest carbon chain is seven carbons so the parent molecule is heptane. With this numbering, there are methyl groups on carbons 3 and 6 and a chlorine on carbon 5.
Substituents are named in alphabetical order and two double bonds result in a diene. Thus, the correct answer is 5-chloro-3,6-dimethyl-1,5-heptadiene.
You must begin counting the carbons so that the first functional substituent has the lowest possible number. In this case, C1 is connected to C2 by the double bond, meaning we start counting from the left.
The longest carbon chain is seven carbons so the parent molecule is heptane. With this numbering, there are methyl groups on carbons 3 and 6 and a chlorine on carbon 5.
Substituents are named in alphabetical order and two double bonds result in a diene. Thus, the correct answer is 5-chloro-3,6-dimethyl-1,5-heptadiene.
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What is the value of
from Huckel's rule for the given aromatic compound?

What is the value of from Huckel's rule for the given aromatic compound?
Huckel's rule states that an aromatic compound must have
delocalized electrons. The electrons in each double bond are delocalized for this molecule. There are nine double bonds, and thus eighteen delocalized electrons.
If 4n+2=18, then n=4.
Huckel's rule states that an aromatic compound must have delocalized electrons. The electrons in each double bond are delocalized for this molecule. There are nine double bonds, and thus eighteen delocalized electrons.
If 4n+2=18, then n=4.
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Which of the following reagents would convert butanone into 2-butene?
Which of the following reagents would convert butanone into 2-butene?
Two sets of reagents are required to convert butanone into 2-butene. First, we use
to reduce the butanone into a 2-butanol. Second, we use heat and acid to dehydrate the butanol and yield the final desired product.
1.
; 2. Heat/
may seem like an acceptable answer choice. However, note that the Grignard reagent converts the butanone into a tertiary alcohol, rather than a secondary alcohol as needed.
Two sets of reagents are required to convert butanone into 2-butene. First, we use to reduce the butanone into a 2-butanol. Second, we use heat and acid to dehydrate the butanol and yield the final desired product.
1. ; 2. Heat/
may seem like an acceptable answer choice. However, note that the Grignard reagent converts the butanone into a tertiary alcohol, rather than a secondary alcohol as needed.
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2-butone is reacted with
to form a product. That product was then heated in acid
to form a final product. What is the final product?
2-butone is reacted with to form a product. That product was then heated in acid
to form a final product. What is the final product?
2-butone is a carbonyl compound that can readily be reduced by
into a secondary alcohol, 2-butanol. When 2-butanol is heated in acid, we get dehydration, which leads to 2-butene.
2-butone is a carbonyl compound that can readily be reduced by into a secondary alcohol, 2-butanol. When 2-butanol is heated in acid, we get dehydration, which leads to 2-butene.
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What is the reactant of the given reaction?

What is the reactant of the given reaction?
This is an addition reaction with 3 products. The unknown reactant reacts with
and gives those three products. Addition reactions begin with double bonded compounds and so these electrons are used to react with some reagent
. One needs to work backwards to figure out how something was formed and in this case, there are mechanistic pathways, and one of the pathways involves a hydride shift. These 3 products often exist in different concentrations after the reaction.
This is an addition reaction with 3 products. The unknown reactant reacts with and gives those three products. Addition reactions begin with double bonded compounds and so these electrons are used to react with some reagent
. One needs to work backwards to figure out how something was formed and in this case, there are mechanistic pathways, and one of the pathways involves a hydride shift. These 3 products often exist in different concentrations after the reaction.
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Which of the following reagents can be used to create a E alkene from an alkyne?
Which of the following reagents can be used to create a E alkene from an alkyne?
Metallic sodium in liquid ammonia creates solvated electrons which can convert an alkyne to an E alkene. The same will not happen when sodium is combined with water, where sodium reacts violently to create sodium hydroxide and hydrogen gas. Lindlar's catalyst is a poisoned catalyst used to form alkenes from alkynes, bud results in a Z conformation. Without the poisoned catalyst, an alkane will be formed.
Metallic sodium in liquid ammonia creates solvated electrons which can convert an alkyne to an E alkene. The same will not happen when sodium is combined with water, where sodium reacts violently to create sodium hydroxide and hydrogen gas. Lindlar's catalyst is a poisoned catalyst used to form alkenes from alkynes, bud results in a Z conformation. Without the poisoned catalyst, an alkane will be formed.
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What is the major product for the reaction given?

What is the major product for the reaction given?
Below is the mechanism for the reaction given to form the alkene:

Below is the mechanism for the reaction given to form the alkene:

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What is the major product for the reaction given?

What is the major product for the reaction given?
The reason this is the major product is because on tertiary alcohols are best dehydrated based on the E1 mechanism below:

The reason this is the major product is because on tertiary alcohols are best dehydrated based on the E1 mechanism below:

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What is the major product for the reaction given?

What is the major product for the reaction given?
The reason this is the major product is because tertiary alcohols are best dehydrated based on the E1 mechanism below:

The reason this is the major product is because tertiary alcohols are best dehydrated based on the E1 mechanism below:

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A secondary alkyl halide is treated with
, then
, then acid. The final product is                     .
A secondary alkyl halide is treated with , then
, then acid. The final product is                     .
The
group replaces the halogen as the halogen is a better leaving group. Lithium aluminum hydride is a strong reducing agent. It takes nitrogen-nitrogen bonds and allows for nitrogen hydrogen bonds to be formed instead. A primary nitrogen is bonded to two hydrogens and one R group. After reduction, a primary amine is formed.
The group replaces the halogen as the halogen is a better leaving group. Lithium aluminum hydride is a strong reducing agent. It takes nitrogen-nitrogen bonds and allows for nitrogen hydrogen bonds to be formed instead. A primary nitrogen is bonded to two hydrogens and one R group. After reduction, a primary amine is formed.
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What product would be obtained for the acid catalyzed reaction shown above?

What product would be obtained for the acid catalyzed reaction shown above?
The reaction given is for the nucleophilic addition of a secondary amine to a ketone. Below is the mechanism for this acid catalyzed reaction:

The protonation of the hydroxyl group makes it a better leaving group.
The reaction given is for the nucleophilic addition of a secondary amine to a ketone. Below is the mechanism for this acid catalyzed reaction:

The protonation of the hydroxyl group makes it a better leaving group.
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Which of the following reactions is NOT a valid synthesis of methyl benzoate?

Which of the following reactions is NOT a valid synthesis of methyl benzoate?

Each reaction is shown, with its name and correct product below.
If you are unsure how the product is obtained through each reaction, use your textbook or internet sources to find a mechanism for each. Reactions I, II, and III are specific examples of substitution reactions, and the last, reaction IV, goes through a more complex addition-elimination reaction to release nitrogen gas.
Working through the mechanism for a reaction is always a certain way to find the product, even if you don't know from the outset what it will be. Just look for the electrophile and nucleophile in each step of the mechanism, and push those arrows!

Each reaction is shown, with its name and correct product below.
If you are unsure how the product is obtained through each reaction, use your textbook or internet sources to find a mechanism for each. Reactions I, II, and III are specific examples of substitution reactions, and the last, reaction IV, goes through a more complex addition-elimination reaction to release nitrogen gas.
Working through the mechanism for a reaction is always a certain way to find the product, even if you don't know from the outset what it will be. Just look for the electrophile and nucleophile in each step of the mechanism, and push those arrows!

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What reagent is required to complete the reaction?

What reagent is required to complete the reaction?
This reaction is completed by tosylating the hydroxyl group to make it a good leaving group (keep in mind the stereochemistry is retained through the tosylation reaction). The second step is an SN2 reaction with the methoxide ion, which gives the correct stereochemistry. HBr will not result in the correct stereochemical product.
This reaction is completed by tosylating the hydroxyl group to make it a good leaving group (keep in mind the stereochemistry is retained through the tosylation reaction). The second step is an SN2 reaction with the methoxide ion, which gives the correct stereochemistry. HBr will not result in the correct stereochemical product.
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What is the product of the reaction between sodium ethoxide and 1-bromopropane?
What is the product of the reaction between sodium ethoxide and 1-bromopropane?
In solution, the sodium in sodium ethoxide will ionize and an
ion will be present.
Bromine is a good leaving group. In the same step, the bromine leaves and the electrons from the ethoxide will attack that carbon. This creates a bond between the carbon and an oxygen.
The final product is an ether with three carbons on one side and two on the other. This is 1-ethoxypropane.
In solution, the sodium in sodium ethoxide will ionize and an ion will be present.
Bromine is a good leaving group. In the same step, the bromine leaves and the electrons from the ethoxide will attack that carbon. This creates a bond between the carbon and an oxygen.
The final product is an ether with three carbons on one side and two on the other. This is 1-ethoxypropane.
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An organic chemist wants to synthesize an ether product. She begins with methanol and ethanol as her substrates. How would she go about synthesizing the desired ether product?
An organic chemist wants to synthesize an ether product. She begins with methanol and ethanol as her substrates. How would she go about synthesizing the desired ether product?
The substrates must be modified in order to attain the desired product. In order to get the desired product, she needs to change one of the alcohol groups into a good leaving group. One way to do this is to react the methanol with
to create a primary tosylate. Because of its advanced resonance, tosylate is an extraordinary leaving group, and so the ethanol is free to attack the modified substrate to form an ether.
The substrates must be modified in order to attain the desired product. In order to get the desired product, she needs to change one of the alcohol groups into a good leaving group. One way to do this is to react the methanol with to create a primary tosylate. Because of its advanced resonance, tosylate is an extraordinary leaving group, and so the ethanol is free to attack the modified substrate to form an ether.
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Consider the following reaction.




In this reaction, two molecules of an alpha-hydroxy acid are condensed with heat to form product. What functional group is created in this reaction?
Consider the following reaction.


In this reaction, two molecules of an alpha-hydroxy acid are condensed with heat to form product. What functional group is created in this reaction?
For this question, we're shown the structures of both the reactants and products, and we're asked to identify which functional group is in the product.
First, let's go through the answer choices and define them. Then, we'll compare that definition with what we see in the product.
Aldehydes are functional groups in which a carbon atom is double bonded to an oxygen atom. The carbon atom must also be bound to at least one hydrogen atom, and to another hydrogen or carbon atom. Usually, aldehydes occur at the terminal ends of a molecule.
Ketones are similar to aldehydes. These functional groups contain a carbon atom double bound to an oxygen atom. In addition, the carbon atom is bound to two other carbon atoms. Thus, ketones tend to be found within a compound, as opposed to at the terminal ends.
Ethers are a class of functional group in which an oxygen atom is situated between two carbon atoms via a single bond.
Carboxylic acids are a functional group in which a carbon is double bound to one oxygen atom, and also single bonded to the oxygen of a hydroxyl group. This functional group does not occur in the product, but it does occur in the reactant.
Esters are a functional group in which a carbon atom is double bonded to an oxygen atom, and also single bonded to another oxygen atom. However, unlike carboxylic acids, esters do not contain a hydroxyl group. Instead, the oxygen atom is bound to another "R group," typically another carbon atom.
Now, let's go ahead and take a look at the product. Shown in red circles, we see that there are two ester groups in the product. Thus, the ester functional group is the correct answer.

For this question, we're shown the structures of both the reactants and products, and we're asked to identify which functional group is in the product.
First, let's go through the answer choices and define them. Then, we'll compare that definition with what we see in the product.
Aldehydes are functional groups in which a carbon atom is double bonded to an oxygen atom. The carbon atom must also be bound to at least one hydrogen atom, and to another hydrogen or carbon atom. Usually, aldehydes occur at the terminal ends of a molecule.
Ketones are similar to aldehydes. These functional groups contain a carbon atom double bound to an oxygen atom. In addition, the carbon atom is bound to two other carbon atoms. Thus, ketones tend to be found within a compound, as opposed to at the terminal ends.
Ethers are a class of functional group in which an oxygen atom is situated between two carbon atoms via a single bond.
Carboxylic acids are a functional group in which a carbon is double bound to one oxygen atom, and also single bonded to the oxygen of a hydroxyl group. This functional group does not occur in the product, but it does occur in the reactant.
Esters are a functional group in which a carbon atom is double bonded to an oxygen atom, and also single bonded to another oxygen atom. However, unlike carboxylic acids, esters do not contain a hydroxyl group. Instead, the oxygen atom is bound to another "R group," typically another carbon atom.
Now, let's go ahead and take a look at the product. Shown in red circles, we see that there are two ester groups in the product. Thus, the ester functional group is the correct answer.

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What is the IUPAC name of the given molecule?

What is the IUPAC name of the given molecule?
The longest carbon chain that can be formed is eight carbons. The base molecule is octane.
Using IUPAC rules, substituents should have the lowest possible numbers; thus, we start counting carbons from the right side rather than the left. If you count from the correct side, there are two methyl groups on carbon 3 and one on carbon 5. Thus, the name of the moleculue is 3,3,5-trimethyloctane.
The longest carbon chain that can be formed is eight carbons. The base molecule is octane.
Using IUPAC rules, substituents should have the lowest possible numbers; thus, we start counting carbons from the right side rather than the left. If you count from the correct side, there are two methyl groups on carbon 3 and one on carbon 5. Thus, the name of the moleculue is 3,3,5-trimethyloctane.
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