Textbook Question
Draw the condensed structural or line-angle formula for the alkene, aldehyde, or ketone product of each of the following reactions:
a.
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14. Compounds with Oxygen or Sulfur
Alcohol Reactions: Dehydration Reactions
2:10 minutesProblem 80
Textbook Question
The reverse reaction of hydration is dehydration. The dehydration of an alcohol involves removing an OH from one carbon and an H from the carbon next to it to form an alkene. In glycolysis, the enzyme enolase catalyzes the dehydration of 2-phosphoglycerate to form phosphoenolpyruvate (PEP), which contains a carbon–carbon double bond. Complete the reaction below by drawing the structure of PEP.
Verified step by step guidance1
Understand the concept of dehydration: Dehydration involves the removal of a water molecule (H₂O) from a compound. In this case, an OH group is removed from one carbon, and an H atom is removed from an adjacent carbon, resulting in the formation of a carbon-carbon double bond (alkene).
Analyze the reactant: The reactant in this reaction is 2-phosphoglycerate, which contains a hydroxyl group (-OH) on one carbon and a hydrogen atom on the adjacent carbon. These are the groups that will be removed during the dehydration process.
Identify the enzyme's role: The enzyme enolase catalyzes the dehydration reaction. Enzymes lower the activation energy of the reaction, making it proceed more efficiently. Enolase specifically facilitates the removal of the OH and H groups to form the double bond.
Determine the product structure: After the removal of the OH group from one carbon and the H atom from the adjacent carbon, a carbon-carbon double bond forms. The product, phosphoenolpyruvate (PEP), retains the phosphate group attached to one of the carbons.
Draw the structure of PEP: To complete the reaction, draw the structure of PEP, ensuring that it includes the carbon-carbon double bond, the phosphate group, and the correct connectivity of atoms. The double bond should be between the two carbons that lost the OH and H groups.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Dehydration Reaction
A dehydration reaction is a chemical process that involves the removal of water (H2O) from a molecule. In organic chemistry, this often occurs when an alcohol loses a hydroxyl group (OH) and a hydrogen atom (H) from adjacent carbon atoms, resulting in the formation of a carbon–carbon double bond, or alkene. This reaction is crucial in various metabolic pathways, including glycolysis.
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Glycolysis
Glycolysis is a fundamental metabolic pathway that breaks down glucose into pyruvate, generating energy in the form of ATP and NADH. It consists of a series of enzymatic reactions, including the dehydration of 2-phosphoglycerate to phosphoenolpyruvate (PEP), which is catalyzed by the enzyme enolase. This pathway is essential for cellular respiration and energy production in both aerobic and anaerobic conditions.
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Phosphoenolpyruvate (PEP)
Phosphoenolpyruvate (PEP) is a high-energy compound formed during glycolysis, characterized by a carbon–carbon double bond and a phosphate group. It plays a critical role in the conversion of glucose to pyruvate and is a key intermediate in various metabolic processes. PEP is also involved in the synthesis of ATP through substrate-level phosphorylation, making it vital for energy metabolism.
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