Reactions by Reactant - Organic Chemistry
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The compound below is reacted with 
. What is the final hybridization around the initially chiral center carbon when the reaction is complete?
The compound below is reacted with
The initially chiral carbon has an 
hybridization. Once treated with 
,an oxidizing agent, the secondary alcohol in the compound is oxidized to a ketone. The central carbon is no longer a chiral center (a carbon with a double bond cannot be chiral), and the double bond (pi-bond) formed between carbon and oxygen gives the molecule an 
hybridization.
hybridization is formed with triple bonds, and an 
hybridization does not exist.
The initially chiral carbon has an
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What is the product of the reaction when the given molecule is introduced to an acidic solution?
What is the product of the reaction when the given molecule is introduced to an acidic solution?
In acidic solution, a hydrogen will be added to the hydroxy group of the given compound. This intermediate is a good leaving group. As it leaves, a hydrogen will be abstracted and a double bond will form. The bond is across carbons two and three becasue those two are more highly substituted than carbon 1, which is primary. The naming begins at the double bond, so the name is 4-bromo-2-hexene.
In acidic solution, a hydrogen will be added to the hydroxy group of the given compound. This intermediate is a good leaving group. As it leaves, a hydrogen will be abstracted and a double bond will form. The bond is across carbons two and three becasue those two are more highly substituted than carbon 1, which is primary. The naming begins at the double bond, so the name is 4-bromo-2-hexene.
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Which reagent(s) would achieve the given synthetic transformation?
Which reagent(s) would achieve the given synthetic transformation?
Chromic acid (formed in-situ via 
), the correct answer, is a powerful oxidizing agent that converts primary alcohols to carboxylic acids. PCC is also an oxidizing agent, but oxidizes primary alcohols one "rung" up the ladder to aldehydes. 
, 
and 
are reducing agents, which react in the opposite direction of the given transformation.
Chromic acid (formed in-situ via
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What is the product of the following reaction?
What is the product of the following reaction?
The key to answering this question is to realize that potassium permanganate 
is a very powerful oxidizing agent. Therefore, the primary alcohol in the reactant will be completely oxidized into a carboxylic acid. It's also important to note that because potassium permanganate is such a powerful oxidizing agent, the primary alcohol will not just stop at the aldehyde level of oxidation, but will go all the way to a carboxylic acid, which is at the highest oxidation level.
The key to answering this question is to realize that potassium permanganate
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Which of the following compounds should be used to convert isopropyl alcohol to isopropyl bromide?
Which of the following compounds should be used to convert isopropyl alcohol to isopropyl bromide?
or thionyl bromide is used to convert secondary alcohols to the bromide product as shown. Isopropyl alcohol is a secondary alcohol because the alcohol group is bonded to a carbon that is bonded to two other carbons.
The following reaction is the bromination of a secondary alcohol:
The following reaction is the bromination of a secondary alcohol:
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When ethanol is reacted with 
(sulfuric acid), an ether forms. What is the identity of the ether formed?
When ethanol is reacted with
The correct answer is diethyl ether because this is the only ether compound listed.
Diethyl ether forms with the addition of a strong acid to ethanol.
The correct answer is diethyl ether because this is the only ether compound listed.
Diethyl ether forms with the addition of a strong acid to ethanol.
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Which of the following molecules are capable of being converted into an aldehyde in one step?
Which of the following molecules are capable of being converted into an aldehyde in one step?
In this question, we're being asked to identify which structure can be converted into an aldehyde in one step.
Now, let's remember what an aldehyde is. Aldehydes, along with ketones, are a carbonyl functional group. This means that it contains a carbon doubled bonded to an oxygen. But with aldehydes, the carbon-oxygen double bond is terminal. That is to say, it is at the end of the molecule, because the carbon atom is also bonded to at least one hydrogen atom.
In looking at the structures given in the answer choices, we see that most of them are alcohols. One of them is a ketone, which cannot be converted into an aldehyde in a single step, so this can be ruled out. For the other answer choices, we can see that we have a primary, secondary, and tertiary alcohol.
Due to the fact that aldehydes occur at the terminal position of a molecule, we know that if we were to start with an alcohol as our reactant, then it must be a primary alcohol. Thus, the only one that fits this is 
In this question, we're being asked to identify which structure can be converted into an aldehyde in one step.
Now, let's remember what an aldehyde is. Aldehydes, along with ketones, are a carbonyl functional group. This means that it contains a carbon doubled bonded to an oxygen. But with aldehydes, the carbon-oxygen double bond is terminal. That is to say, it is at the end of the molecule, because the carbon atom is also bonded to at least one hydrogen atom.
In looking at the structures given in the answer choices, we see that most of them are alcohols. One of them is a ketone, which cannot be converted into an aldehyde in a single step, so this can be ruled out. For the other answer choices, we can see that we have a primary, secondary, and tertiary alcohol.
Due to the fact that aldehydes occur at the terminal position of a molecule, we know that if we were to start with an alcohol as our reactant, then it must be a primary alcohol. Thus, the only one that fits this is
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What is the product of the reaction between 2-butanone and lithium aluminum hydride?
What is the product of the reaction between 2-butanone and lithium aluminum hydride?
Lithium aluminum hydride is a reducing agent. It reduces ketones and carboxylic acids to alcohols. 2-butanone is a 4-carbon chain with a double bond between an oxygen and carbon 2. The reduction turns the double bond with oxygen into a single bond to a hydroxy group. This makes the product 2-butanol.
Lithium aluminum hydride is a reducing agent. It reduces ketones and carboxylic acids to alcohols. 2-butanone is a 4-carbon chain with a double bond between an oxygen and carbon 2. The reduction turns the double bond with oxygen into a single bond to a hydroxy group. This makes the product 2-butanol.
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What is the product of the given reaction?
What is the product of the given reaction?
This is a Grignard reagent carbon-carbon bond forming reaction. This reaction is being used with an ester which goes through a ketone intermediate with requires a second attack form the organolithium to reduce to an alcohol. Esters and acyl chlorides go to an alcohol with two of the same R groups from the organolithium in a Grignard reaction. This structure fits the bill:
This is a Grignard reagent carbon-carbon bond forming reaction. This reaction is being used with an ester which goes through a ketone intermediate with requires a second attack form the organolithium to reduce to an alcohol. Esters and acyl chlorides go to an alcohol with two of the same R groups from the organolithium in a Grignard reaction. This structure fits the bill:
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Choose the appropriate starting compound based on the reaction conditions and major product shown in the figure.
Choose the appropriate starting compound based on the reaction conditions and major product shown in the figure.
In the presence of a strong base and benzene, ethylene glycol will convert ketones to acetals as seen in the product shown above. The given reagents will not react with esters or alcohols. The only given compound containing a ketone is molecule IV, the correct answer. This type of reaction is useful in organic synthesis when reaction at an ester is desired, but a ketone must be protected from reacting simultaneously. The acetal formed is often called a protecting group and may be reversed by addition of acid.
In the presence of a strong base and benzene, ethylene glycol will convert ketones to acetals as seen in the product shown above. The given reagents will not react with esters or alcohols. The only given compound containing a ketone is molecule IV, the correct answer. This type of reaction is useful in organic synthesis when reaction at an ester is desired, but a ketone must be protected from reacting simultaneously. The acetal formed is often called a protecting group and may be reversed by addition of acid.
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Which of the labeled hydrogens in the given molecule is the most acidic?
Which of the labeled hydrogens in the given molecule is the most acidic?
This question is asking what the most acidic hydrogen is in an aldehyde. To identify the most acidic hydrogen, we'll need to consider which conjugate base will be the most stable after the loss of hydrogen. When the alpha-hydrogen is lost, the resulting carbanion will be the most stabilized due to resonance with the adjacent carbonyl group. This resonance helps to distribute the negative charge on the carbanion over a greater area, which contributes to the greater stability of this conjugate base. Abstraction of a hydrogen from any of the other position would result in a carbanion that could not participate in resonance and thus would not be as stable.
This question is asking what the most acidic hydrogen is in an aldehyde. To identify the most acidic hydrogen, we'll need to consider which conjugate base will be the most stable after the loss of hydrogen. When the alpha-hydrogen is lost, the resulting carbanion will be the most stabilized due to resonance with the adjacent carbonyl group. This resonance helps to distribute the negative charge on the carbanion over a greater area, which contributes to the greater stability of this conjugate base. Abstraction of a hydrogen from any of the other position would result in a carbanion that could not participate in resonance and thus would not be as stable.
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If the given compound is reacted with 
, what would the product be?
If the given compound is reacted with
LiAlH4 is a very strong reducing agent and it is a reactant that can reduce acyl chlorides into alcohols. There are 2 alcohols to choose from and now it needs to be known that LiAlH4 doesn't add anything but hydrogens to its substrate. (Note that in the correct answer, there is another H that is not drawn on the carbon bearing the hydroxyl group).
LiAlH4 is a very strong reducing agent and it is a reactant that can reduce acyl chlorides into alcohols. There are 2 alcohols to choose from and now it needs to be known that LiAlH4 doesn't add anything but hydrogens to its substrate. (Note that in the correct answer, there is another H that is not drawn on the carbon bearing the hydroxyl group).
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What is the product of the reaction given?
What is the product of the reaction given?
Below is the mechanism for the reaction given which is called the McMurry Reaction. It is a titanium (Ti) prompted pinacol coupling followed by deoxygenation.
Below is the mechanism for the reaction given which is called the McMurry Reaction. It is a titanium (Ti) prompted pinacol coupling followed by deoxygenation.
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What is the product of the reaction given?
What is the product of the reaction given?
Below is the mechanism for the reaction given which is called the McMurry Reaction. It is a titanium (Ti) prompted pinacol coupling followed by deoxygenation.
Below is the mechanism for the reaction given which is called the McMurry Reaction. It is a titanium (Ti) prompted pinacol coupling followed by deoxygenation.
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In an aprotic solvent, what would be the product of the reaction given?
In an aprotic solvent, what would be the product of the reaction given?
This reaction involves the generation of a radical by single electron transfer that couple through carbon-carbon bond formation to form the product pinacol. This reaction as shown below occurs in an aprotic solvlent:
This reaction involves the generation of a radical by single electron transfer that couple through carbon-carbon bond formation to form the product pinacol. This reaction as shown below occurs in an aprotic solvlent:
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Which of the following can reduce an alkene to an alkane?
Which of the following can reduce an alkene to an alkane?
Neither lithium aluminum hydride, nor sodium borohydride will reduce C–C double bonds.
H2/Raney nickel and H2/Pd can each (individually) reduce an alkene to an alkane. Since both H2/Raney nickel and H2/Pd can reduce the alkene, the answer is both of those reagents. This is a catalytic hydrogenation reaction, and H2/Raney nickel not only reduces C–C double bonds, but also carbonyl compounds.
Neither lithium aluminum hydride, nor sodium borohydride will reduce C–C double bonds.
H2/Raney nickel and H2/Pd can each (individually) reduce an alkene to an alkane. Since both H2/Raney nickel and H2/Pd can reduce the alkene, the answer is both of those reagents. This is a catalytic hydrogenation reaction, and H2/Raney nickel not only reduces C–C double bonds, but also carbonyl compounds.
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Identify the major organic product expected from the acid-catalyzed dehydration of 2-methyl-2-pentanol.
Identify the major organic product expected from the acid-catalyzed dehydration of 2-methyl-2-pentanol.
The initial compound is a five-carbon alkane chain with methyl and hydroxy groups on the second carbon. Dehydration involves the hydrogenation of the hydroxy group. That group then leaves, and a double bond is formed. Zaitsev's rule states that double bonds are more stable on more highly substituted carbons. The double bond forms across carbons two and three.
The initial compound is a five-carbon alkane chain with methyl and hydroxy groups on the second carbon. Dehydration involves the hydrogenation of the hydroxy group. That group then leaves, and a double bond is formed. Zaitsev's rule states that double bonds are more stable on more highly substituted carbons. The double bond forms across carbons two and three.
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If an alkane is reacted with excess 
in a high temperature environment, what are the products formed?
If an alkane is reacted with excess
Whenever an alkane is reacted with excess oxygen in a high temperature reaction, the reaction is known as combustion. Combustion of an alkane always produces carbon dioxide gas and water vapor.
Therefore the correct answer is: 
and 
.
Whenever an alkane is reacted with excess oxygen in a high temperature reaction, the reaction is known as combustion. Combustion of an alkane always produces carbon dioxide gas and water vapor.
Therefore the correct answer is:
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The stereochemical pathway for the hydrogenation of an alkene with a metal catalyst, such as platinum, occurs via __________.
The stereochemical pathway for the hydrogenation of an alkene with a metal catalyst, such as platinum, occurs via __________.
Hydrogenation of an alkene with a metal catalyst, such as platinum, occurs via syn addition.
It is important to note the three main types of reactions for alkenes. The first type of reaction is a 2-step mechanism in which the electrophile attacks the carbocation nucleophile. This can yield syn or anti products. The second type of reaction is a 2-step mechanism that forms a bridged carbocation as the intermediate. This can yield only anti products. The third and last type of reaction is a 1-step addition. This can only yield syn products.
An example of the third type of reaction is the addition of a hydrogen with palladium, platinum, or nickel as demonstrated in the picture.
Hydrogenation of an alkene with a metal catalyst, such as platinum, occurs via syn addition.
It is important to note the three main types of reactions for alkenes. The first type of reaction is a 2-step mechanism in which the electrophile attacks the carbocation nucleophile. This can yield syn or anti products. The second type of reaction is a 2-step mechanism that forms a bridged carbocation as the intermediate. This can yield only anti products. The third and last type of reaction is a 1-step addition. This can only yield syn products.
An example of the third type of reaction is the addition of a hydrogen with palladium, platinum, or nickel as demonstrated in the picture.
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What is(are) the product(s) in the Pd-catalyzed hydrogenation if 1,2-dimethylcyclopentene?
What is(are) the product(s) in the Pd-catalyzed hydrogenation if 1,2-dimethylcyclopentene?
The product for this hydrogenation is _cis-_1,2-dimethylcyclopentane.
It is important to note the three main types of reactions for alkenes. The first type of reaction is a 2-step mechanism in which the electrophile attacks the carbocation nucleophile. This can yield syn or anti products. The second type of reaction is a 2-step mechanism that forms a bridged carbocation as the intermediate. This can yield only anti products. The third and last type of reaction is a 1-step addition. This can only yield syn products.
The cis product alone forms because the reagents used were hydrogen and a metal catalyst palladium (other common metal catalysts are platinum and nickel). This type of reagent with an alkene will always be a 1-step addition that yields solely syn products. Cis-1,2-dimethylcyclopentane is the only answer that solely indicates syn products.
The product for this hydrogenation is _cis-_1,2-dimethylcyclopentane.
It is important to note the three main types of reactions for alkenes. The first type of reaction is a 2-step mechanism in which the electrophile attacks the carbocation nucleophile. This can yield syn or anti products. The second type of reaction is a 2-step mechanism that forms a bridged carbocation as the intermediate. This can yield only anti products. The third and last type of reaction is a 1-step addition. This can only yield syn products.
The cis product alone forms because the reagents used were hydrogen and a metal catalyst palladium (other common metal catalysts are platinum and nickel). This type of reagent with an alkene will always be a 1-step addition that yields solely syn products. Cis-1,2-dimethylcyclopentane is the only answer that solely indicates syn products.
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