Help with Alkene Synthesis - Organic Chemistry
Card 1 of 36

What is the IUPAC name of the given diene?

What is the IUPAC name of the given diene?
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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?
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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?
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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?
Tap to reveal answer
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?
Tap to reveal answer
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?
Tap to reveal answer
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?
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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?
Tap to reveal answer
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?
Tap to reveal answer
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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What is the IUPAC name of the given diene?

What is the IUPAC name of the given diene?
Tap to reveal answer
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?
Tap to reveal answer
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?
Tap to reveal answer
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?
Tap to reveal answer
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?
Tap to reveal answer
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?
Tap to reveal answer
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?
Tap to reveal answer
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?
Tap to reveal answer
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?
Tap to reveal answer
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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What is the IUPAC name of the given diene?

What is the IUPAC name of the given diene?
Tap to reveal answer
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?
Tap to reveal answer
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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