Chapter 14: Problem 130
\(\alpha\) -D-glucose reacts with \(\mathrm{CH}_{3} \mathrm{OH}\) in the presence of dry HCl gas to form acetal. How many \(\mathrm{CH}_{3} \mathrm{OH}\) molecule are used by per molecule of glucose? (a) 2 (b) 1 (c) 5 (d) 6
Short Answer
Expert verified
The answer is (c) 5.
Step by step solution
01
Understanding the reaction
Understand that \(\alpha\)-D-glucose is a monosaccharide with five hydroxyl (-OH) groups that can potentially react with methanol (\(\mathrm{CH}_3 \mathrm{OH}\)) to form acetals. Acetal formation is a reaction where a carbonyl group on glucose reacts with an alcohol in the presence of an acid catalyst.
02
Identifying reactive sites on glucose
Identify that in the case of \(\alpha\)-D-glucose, the reaction to form an acetal involves the aldehyde group at the first carbon and the hydroxyl groups at the other carbon positions. In a fully protected \(\alpha\)-D-glucose molecule, all these groups can potentially react with \(\mathrm{CH}_3 \mathrm{OH}\) to form acetals.
03
Counting the number of methanol molecules required
Count that \(\alpha\)-D-glucose can react with one molecule of \(\mathrm{CH}_3 \mathrm{OH}\) per hydroxyl group, plus one additional \(\mathrm{CH}_3 \mathrm{OH}\) for the aldehyde group. Since glucose has four hydroxyl groups that can react with methanol to form acetals, and one aldehyde group that can also react, the total number of methanol molecules needed is five.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Alpha-D-Glucose
Alpha-D-Glucose is a vital monosaccharide in biochemistry and the building block of many carbohydrates. Classified as an aldohexose, it contains six carbon atoms, with the first one being part of an aldehyde group. The 'alpha' denotes the configuration of the hydroxyl group (-OH) attached to the first carbon; it is opposite to the CH2OH group on the fifth carbon when drawn in the Haworth projection. This specific orientation greatly affects the chemical reactivity and biological role of the glucose molecule.
In water solutions, alpha-D-glucose exists in equilibrium with the beta-D-glucose form, as well as a small percentage in the open-chain form. However, when reacting to form acetals, like in the original exercise, it's important to note that it is the cyclic form of alpha-D-glucose that reacts with alcohols to form a glycosidic bond, leading to the acetal. This characteristic is crucial for understanding the reactivity and the interaction with other molecules, especially in the context of carbohydrate chemistry.
In water solutions, alpha-D-glucose exists in equilibrium with the beta-D-glucose form, as well as a small percentage in the open-chain form. However, when reacting to form acetals, like in the original exercise, it's important to note that it is the cyclic form of alpha-D-glucose that reacts with alcohols to form a glycosidic bond, leading to the acetal. This characteristic is crucial for understanding the reactivity and the interaction with other molecules, especially in the context of carbohydrate chemistry.
Acetal Reaction Mechanism
Acetal formation is a fundamental mechanism of carbohydrate chemistry. The process starts with a hemiacetal, an intermediate which forms when an aldehyde reacts with an alcohol. In the presence of an acidic catalyst, hemiacetal can further react with a second alcohol molecule to form an acetal.
The mechanism involves two key steps: the creation of the hemiacetal and its subsequent conversion to an acetal. Initially, the acidic conditions protonate the oxygen of the aldehyde, making the carbon more electrophilic, which then allows the alcohol to attack and form the hemiacetal. The second step is the nucleophilic attack by another alcohol molecule on the hemiacetal to form a full acetal.
The mechanism involves two key steps: the creation of the hemiacetal and its subsequent conversion to an acetal. Initially, the acidic conditions protonate the oxygen of the aldehyde, making the carbon more electrophilic, which then allows the alcohol to attack and form the hemiacetal. The second step is the nucleophilic attack by another alcohol molecule on the hemiacetal to form a full acetal.
Key Points in Acetal Formation
- Formation of hemiacetal from the aldehyde and alcohol.
- Conversion of hemiacetal to acetal by reaction with a second alcohol molecule.
Carbohydrate Chemistry for NEET
Carbohydrate chemistry is a critical subject in the NEET (National Eligibility cum Entrance Test) syllabus for students aspiring to enter the medical field. Mastering the concepts of how carbohydrates function, including their structures and the reactions they undergo, is essential. In the context of acetal formation, NEET aspirants should understand the role of carbohydrates as protective groups and their reactions with alcohols to form acetals, which is often tested in the exam.
For competitive exams like NEET, the focus should be on conceptual clarity and application. Students must be able to identify functional groups, predict chemical behavior, and apply reaction mechanisms in various scenarios. They should practice such transformations to develop a strong foothold in organic chemistry. For instance, knowing that alpha-D-glucose can form acetals with alcohols, as in the original exercise, and understanding the underlying mechanism, are the types of knowledge that can score well in exams like NEET.
For competitive exams like NEET, the focus should be on conceptual clarity and application. Students must be able to identify functional groups, predict chemical behavior, and apply reaction mechanisms in various scenarios. They should practice such transformations to develop a strong foothold in organic chemistry. For instance, knowing that alpha-D-glucose can form acetals with alcohols, as in the original exercise, and understanding the underlying mechanism, are the types of knowledge that can score well in exams like NEET.
Tips for NEET Preparation
- Thoroughly learn the structures and forms of carbohydrates.
- Understand the mechanisms of key reactions, such as acetal formation.
- Apply the concepts in practice problems to build a strong foundation.