CUET UG Chemistry Booster Test - 2 Structure and Reactions of Carbohydrates
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QUESTION 1 OF 20
Consider the following statements regarding the carbohydrate formula:
1. The general formula is Cx(H₂O)y, and glucose accurately fits it as C₆(H₂O)₆.
2. Rhamnose (C₆H₁₂O₅) is a carbohydrate but does not fit the hydrate formula.
3. Acetic acid [C₂(H₂O)₂] fits the formula and is therefore classified as a carbohydrate.
Which of the above are correct?
QUESTION 2 OF 20
The chemical formation of n-hexane upon prolonged heating of glucose with HI signifies that:
QUESTION 3 OF 20
Which of the following reactions specifically confirms the presence of a carbonyl group (>C=O) in glucose but does not inherently distinguish whether it is an aldehyde or ketone?
QUESTION 4 OF 20
What is the specific stable compound formed when glucose is treated with acetic anhydride, validating the presence of five separate –OH groups?
QUESTION 5 OF 20
QUESTION 6 OF 20
QUESTION 7 OF 20
In the notation D-(+)-glucose, the (+) symbol specifically quantifies which of the following parameters?
QUESTION 8 OF 20
Match the stereochemical terms with their correct implications for glucose.
| List I | List II |
|---|---|
| 1. — D-configuration | a. — Dextrorotatory nature |
| 2. — L-configuration | b. — –OH on the lowest asymmetric carbon is on the left |
| 3. — (+) rotation | c. — Laevorotatory nature |
| 4. — (–) rotation | d. — Correlates to (+)-glyceraldehyde |
QUESTION 9 OF 20
Arrange the following physical parameters of glucose anomers in decreasing numerical order (highest K to lowest K):
A. Melting point of β-form
B. Melting point of α-form
C. Crystallisation temperature of β-form from hot saturated solution
D. Crystallisation temperature of α-form from concentrated solution
QUESTION 10 OF 20
The pyranose structure of glucose involves a cyclic hemiacetal. Which carbon's hydroxyl group is specifically involved in the ring formation with the aldehyde group?
QUESTION 11 OF 20
Regarding the α-form of glucose, which of the following statements is true?
1. It differs from the β-form strictly in the configuration at C-1.
2. It is obtained by crystallisation from a concentrated glucose solution at 371 K.
3. It possesses a higher melting point than the β-form.
QUESTION 12 OF 20
The uniquely identifiable C1 carbon in the cyclic hemiacetal structure of glucose, which determines whether the molecule is the α-form or β-form, is named the:
QUESTION 13 OF 20
Unlike the six-membered pyranose ring of glucose, fructose forms a five-membered furanose ring. This relies on the addition of the –OH group at which carbon to the ketonic group?
QUESTION 14 OF 20
Despite being a ketose, fructose exhibits certain optical reaction phenomena. Which structural feature explicitly dictates why it is appropriately written as D-(–)-fructose?
QUESTION 15 OF 20
When a robust glycosidic linkage structurally forms between two monosaccharides, which molecule is eliminated in the process?
QUESTION 16 OF 20
Match the disaccharide with its correct chemical hydrolysis products.
| List I | List II |
|---|---|
| 1. — Sucrose | a. — Two molecules of α-D-glucose |
| 2. — Maltose | b. — Equimolar mixture of D-(+)-glucose and D-(–)-fructose |
| 3. — Lactose | c. — β-D-galactose and β-D-glucose |
QUESTION 17 OF 20
Why is sucrose termed a non-reducing sugar while maltose is a reducing sugar?
QUESTION 18 OF 20
Maltose possesses reducing properties primarily because:
QUESTION 19 OF 20
The exact sequence of the glycosidic linkage in lactose occurs between:
QUESTION 20 OF 20
Which specific common name is assigned to lactose due to the environment of its primary natural occurrence?
Test Complete!
Answer Review
1 Consider the following statements regarding the carbohydrate formula:
1. The general formula is Cx(H₂O)y, and glucose accurately fits it as C₆(H₂O)₆.
2. Rhamnose (C₆H₁₂O₅) is a carbohydrate but does not fit the hydrate formula.
3. Acetic acid [C₂(H₂O)₂] fits the formula and is therefore classified as a carbohydrate.
Which of the above are correct?
�� Glucose fits the general hydrate formula. �� Rhamnose is an exception among carbohydrates. �� Acetic acid is not a carbohydrate despite fitting the formula.
Statement 1 is correct because glucose can be represented as C₆(H₂O)₆. Statement 2 is correct because rhamnose is a carbohydrate but does not satisfy the general hydrate formula. Statement 3 is incorrect because acetic acid is a carboxylic acid, not a carbohydrate, even though its formula can be written as C₂(H₂O)₂. Therefore, Statements 1 and 2 are correct.
- �� Option B → Statement 3 is incorrect.
- �� Option C → Statement 2 is also correct.
- �� Option D → Includes incorrect Statement 3.
Used
- Exception-Based Elimination
Application:
- Identify compounds that fit the formula but are not carbohydrates.
Final Logic:
- Statements 1 and 2 are true; Statement 3 is false.
Formula Fits ≠ Carbohydrate
2 The chemical formation of n-hexane upon prolonged heating of glucose with HI signifies that:
�� HI reduces glucose to n-hexane. �� n-Hexane possesses a straight carbon chain. �� This proves glucose has an unbranched skeleton.
On prolonged heating with HI, glucose is reduced to n-hexane. Since n-hexane contains six carbon atoms arranged in a straight chain without branching, this proves that the carbon skeleton of glucose is also unbranched. Thus, glucose possesses a straight-chain carbon framework.
- �� Option A → Aldehyde presence is confirmed by oxidation reactions.
- �� Option C → HI reduction does not directly prove hydroxyl positions.
- �� Option D → HI reduction supports the carbon chain structure, not pyranose formation.
Used
- Reaction Interpretation
Application:
- Identify the structural information obtained from HI reduction.
Final Logic:
- n-Hexane formation confirms an unbranched six-carbon chain.
HI → Hexane → Straight Chain
3 Which of the following reactions specifically confirms the presence of a carbonyl group (>C=O) in glucose but does not inherently distinguish whether it is an aldehyde or ketone?
�� Aldehydes and ketones both form oximes. �� Oxime formation confirms a carbonyl group. �� It does not distinguish aldehyde from ketone.
Hydroxylamine reacts with carbonyl compounds to form oximes. Since both aldehydes and ketones undergo this reaction, oxime formation confirms the presence of a carbonyl group but does not identify whether the carbonyl is aldehydic or ketonic. Therefore, oxime formation is evidence for a carbonyl group.
- �� Option A → Gives oxidation information.
- �� Option C → Confirms hydroxyl groups.
- Option D → Specifically confirms an aldehyde group.
Used
- Functional Group Analysis
Application:
- Identify the reaction common to aldehydes and ketones.
Final Logic:
- Oxime formation proves carbonyl presence.
Oxime = Carbonyl Proof
4 What is the specific stable compound formed when glucose is treated with acetic anhydride, validating the presence of five separate –OH groups?
�� Acetic anhydride acetylates hydroxyl groups. �� Five hydroxyl groups are acetylated. �� The product formed is glucose pentaacetate.
Glucose reacts with acetic anhydride to produce glucose pentaacetate. The formation of a pentaacetate derivative confirms the presence of five hydroxyl groups in the glucose molecule. Thus, glucose pentaacetate provides direct evidence for five –OH groups.
- �� Option A → Not formed during acetylation.
- �� Option C → Produced by oxidation with bromine water.
- �� Option D → Produced by oxidation with nitric acid.
Used
- Reaction Identification
Application:
- Identify the product formed during acetylation.
Final Logic:
- Pentaacetate confirms five hydroxyl groups.
Pentaacetate = 5 OH Groups
5
�� Bromine water is a mild oxidising agent. �� It oxidises aldehydes to carboxylic acids. �� Gluconic acid formation proves an aldehyde group.
Bromine water oxidises the aldehydic group of glucose to form gluconic acid. Since ketones do not undergo this reaction under similar conditions, the reaction confirms that glucose contains a terminal aldehyde group. Therefore, glucose is an aldohexose.
- �� Option A → Not demonstrated by bromine water oxidation.
- �� Option B → Established through HI reduction.
- �� Option D → Not proven by oxidation.
Used
- Passage-Based Analysis
Application:
- Determine which functional group is oxidised.
Final Logic:
- Gluconic acid formation proves an aldehydic group.
Bromine Water → Aldehyde Proof
6
�� Gluconic acid already contains one carboxyl group. �� Nitric acid oxidises the terminal alcohol. �� A second carboxyl group is formed.
Gluconic acid already possesses one carboxyl group at C-1. When nitric acid oxidises the primary alcohol present at C-6, another carboxyl group is formed, producing saccharic acid. This conversion proves the presence of a terminal primary alcohol group in glucose.
- �� Option A → Nitric acid oxidises primary alcohols as well.
- �� Option C → No carbon-chain cleavage occurs.
- �� Option D → The important evidence comes from oxidation of the alcohol group.
Used
- Passage-Based Analysis
Application:
- Track the structural change from monoacid to diacid.
Final Logic:
- Second carboxyl group arises from oxidation of a primary alcohol.
Monoacid → Diacid = Primary Alcohol Present
7 In the notation D-(+)-glucose, the (+) symbol specifically quantifies which of the following parameters?
�� (+) indicates optical rotation. �� Positive rotation means rightward rotation. �� It does not indicate configuration.
The (+) sign denotes that glucose rotates plane-polarised light to the right and is therefore dextrorotatory. This notation is related to optical activity and is independent of D/L configuration. Thus, (+) signifies positive optical rotation.
- ��Option A → Does not describe anomeric composition.
- Option B → Refers to D-configuration, not optical rotation.
- �� Option C → Unrelated.
Used
- Concept Clarification
Application:
- Differentiate configuration from optical activity.
Final Logic:
- (+) means dextrorotatory.
Plus = Right Rotation
8 Match the stereochemical terms with their correct implications for glucose.
| List I | List II |
|---|---|
| 1. — D-configuration | a. — Dextrorotatory nature |
| 2. — L-configuration | b. — –OH on the lowest asymmetric carbon is on the left |
| 3. — (+) rotation | c. — Laevorotatory nature |
| 4. — (–) rotation | d. — Correlates to (+)-glyceraldehyde |
�� D/L refers to configuration. �� (+)/(–) refers to optical rotation. �� The two concepts are independent.
Matching: • D-configuration → Correlates with (+)-glyceraldehyde • L-configuration → OH group on lowest asymmetric carbon is on the left • (+) rotation → Dextrorotatory • (–) rotation → Laevorotatory Hence: 1-d, 2-b, 3-a, 4-c
- �� Options B, C and D contain incorrect stereochemical associations.
Used
- Option Grouping
Application:
- Match configuration terms with their meanings.
Final Logic:
- Only Option A provides all correct matches.
D/L = Configuration; +/– = Rotation
9 Arrange the following physical parameters of glucose anomers in decreasing numerical order (highest K to lowest K):
A. Melting point of β-form
B. Melting point of α-form
C. Crystallisation temperature of β-form from hot saturated solution
D. Crystallisation temperature of α-form from concentrated solution
- β-form melting point = 423 K.
- α-form melting point = 419 K.
- Crystallisation temperatures are 371 K and 303 K.
The values are:
- β-form melting point = 423 K
- α-form melting point = 419 K
- β-form crystallisation temperature = 371 K
- α-form crystallisation temperature = 303 K
Therefore:
423 K > 419 K > 371 K > 303 K
Hence the order is A > B > C > D, which corresponds to Option 1.
- Option 2 incorrectly arranges the numerical values.
- Option 3 incorrectly arranges the numerical values.
- Option 4 incorrectly arranges the numerical values.
Ordering
Application:
Arrange the given temperatures from highest to lowest.
Final Logic:
423 > 419 > 371 > 303.
423 > 419 > 371 > 303
10 The pyranose structure of glucose involves a cyclic hemiacetal. Which carbon's hydroxyl group is specifically involved in the ring formation with the aldehyde group?
�� The aldehyde group is present at C-1. �� The hydroxyl group at C-5 reacts intramolecularly. �� A six-membered pyranose ring is formed.
In glucose, the hydroxyl group attached to C-5 reacts with the aldehyde group at C-1 to form a cyclic hemiacetal. This intramolecular reaction produces the six-membered pyranose ring structure. Therefore, the hydroxyl group involved belongs to C-5.
- �� Option A → Does not form the stable pyranose ring.
- �� Option B → Not involved in the major ring formation.
- �� Option D → Does not participate in hemiacetal formation.
Used
- Structural Analysis
Application:
- Identify the hydroxyl group participating in cyclisation.
Final Logic:
- C-5 OH forms the pyranose ring.
C1 + C5 = Pyranose Ring
11 Regarding the α-form of glucose, which of the following statements is true?
1. It differs from the β-form strictly in the configuration at C-1.
2. It is obtained by crystallisation from a concentrated glucose solution at 371 K.
3. It possesses a higher melting point than the β-form.
�� α- and β-glucose differ only at C-1. �� α-Glucose crystallises at 303 K, not 371 K. �� β-Glucose has the higher melting point.
Statement 1 is correct because α- and β-glucose differ only in the configuration of the hydroxyl group attached to the anomeric carbon (C-1). Statement 2 is incorrect because α-glucose is obtained by crystallisation from a concentrated solution at 303 K, whereas 371 K is associated with β-glucose. Statement 3 is incorrect because β-glucose has a melting point of 423 K, which is higher than the melting point of α-glucose (419 K). Therefore, only Statement 1 is correct.
- �� Option B → Statement 2 is incorrect.
- �� Option C → Statement 3 is incorrect.
- �� Option D → Statement 3 is incorrect.
Used
- Statement Verification
Application:
- Evaluate each statement using known properties of α- and β-glucose.
Final Logic:
- Only Statement 1 is true.
Alpha = 303 K, Beta = Higher MP
12 The uniquely identifiable C1 carbon in the cyclic hemiacetal structure of glucose, which determines whether the molecule is the α-form or β-form, is named the:
�� C-1 becomes a new chiral centre after cyclisation. �� α and β forms differ at this carbon. �� It is called the anomeric carbon.
During cyclisation of glucose, the aldehyde carbon (C-1) becomes a new stereogenic centre. The orientation of the hydroxyl group attached to this carbon determines whether the molecule exists as α-glucose or β-glucose. This carbon is known as the anomeric carbon.
- �� Option A → Epimers differ at any one chiral carbon, not specifically C-1.
- �� Option B → Not a recognized term for C-1 in glucose.
- �� Option D → Not used in carbohydrate nomenclature.
Used
- Keyword Identification
Application:
- Identify the carbon responsible for anomerism.
Final Logic:
- C-1 in cyclic glucose is the anomeric carbon.
Anomer = Anomeric Carbon
13 Unlike the six-membered pyranose ring of glucose, fructose forms a five-membered furanose ring. This relies on the addition of the –OH group at which carbon to the ketonic group?
�� Fructose contains a ketonic group at C-2. �� The hydroxyl group at C-5 participates in ring formation. �� This produces a five-membered furanose ring.
In fructose, the hydroxyl group attached to C-5 reacts with the ketonic carbon at C-2 to form a cyclic hemiketal. This intramolecular reaction generates a five-membered furanose ring structure. Therefore, the hydroxyl group involved belongs to C-5.
- �� Option A → Does not produce the common furanose ring.
- �� Option C → Not involved in standard furanose formation.
- �� Option D → Does not participate in the major cyclic structure.
Used
- Structural Analysis
Application:
- Identify the hydroxyl group participating in cyclisation.
Final Logic:
- C-5 hydroxyl reacts with the C-2 ketonic group.
Fructose: C2 Keto + C5 OH
14 Despite being a ketose, fructose exhibits certain optical reaction phenomena. Which structural feature explicitly dictates why it is appropriately written as D-(–)-fructose?
�� D/L refers to configuration. �� (+)/(–) refers to optical rotation. �� D-fructose rotates light to the left.
The D-notation of fructose is assigned by comparing the configuration of its lowest asymmetric carbon with (+)-glyceraldehyde. However, its optical rotation is negative, meaning it rotates plane-polarised light to the left. Therefore, fructose is correctly represented as D-(–)-fructose.
- �� Option A → D-fructose is laevorotatory, not dextrorotatory.
- �� Option C → Fructose is a ketose.
- �� Option D → Fructose predominantly forms a furanose ring.
Used
- Concept Clarification
Application:
- Separate configuration from optical activity.
Final Logic:
- D and (–) describe different properties.
D ≠ Dextrorotatory
15 When a robust glycosidic linkage structurally forms between two monosaccharides, which molecule is eliminated in the process?
�� Glycosidic bonds form through condensation. �� Condensation removes water. �� The resulting linkage joins monosaccharides.
Formation of a glycosidic bond occurs through a condensation reaction between two monosaccharides. During this process, one molecule of water is eliminated. Thus, water is the molecule removed during glycosidic bond formation.
- �� Option A → Hydrogen gas is not released.
- �� Option B → Carbon dioxide is not produced.
- �� Option D → Oxygen is not removed independently.
Used
- Reaction Analysis
Application:
- Recall the mechanism of glycosidic bond formation.
Final Logic:
- Condensation releases water.
Glycosidic Bond = Loss of H₂O
16 Match the disaccharide with its correct chemical hydrolysis products.
| List I | List II |
|---|---|
| 1. — Sucrose | a. — Two molecules of α-D-glucose |
| 2. — Maltose | b. — Equimolar mixture of D-(+)-glucose and D-(–)-fructose |
| 3. — Lactose | c. — β-D-galactose and β-D-glucose |
�� Sucrose → Glucose + Fructose �� Maltose → Glucose + Glucose �� Lactose → Galactose + Glucose
Matching: • Sucrose → Equimolar mixture of D-(+)-glucose and D-(–)-fructose • Maltose → Two molecules of α-D-glucose • Lactose → β-D-galactose and β-D-glucose Thus: 1-b, 2-a, 3-c
- �� Options B, C and D contain incorrect hydrolysis products.
Used
- Option Grouping
Application:
- Match each disaccharide with its hydrolysis products.
Final Logic:
- Only Option A provides all correct matches.
Sucrose GF, Maltose GG, Lactose Gal-Glu
17 Why is sucrose termed a non-reducing sugar while maltose is a reducing sugar?
- Sucrose has no free reducing group.
- Both anomeric carbons participate in bonding.
- Therefore sucrose is non-reducing.
In sucrose, the anomeric carbon of glucose and the anomeric carbon of fructose are both involved in glycosidic bond formation. Since no free aldehydic or ketonic group can be generated, sucrose cannot act as a reducing sugar.
Hence, sucrose is non-reducing whereas maltose possesses a free reducing end.
- Option 1 → Sucrose contains glucose and fructose, not two glucose units.
- Option 3 → Hydrolysis product does not explain non-reducing behavior.
- Option 4 → Not the reason for non-reducing nature.
Functional Group Analysis
Application:
Determine whether a free reducing group exists.
Final Logic:
No free reducing group = Non-reducing sugar.
Sucrose = Locked Ends
18 Maltose possesses reducing properties primarily because:
�� Maltose contains a free anomeric carbon. �� This carbon can generate an aldehyde group. �� Hence maltose behaves as a reducing sugar.
The glycosidic bond in maltose involves only one anomeric carbon. The second glucose unit retains a free anomeric carbon that can open into the aldehydic form in solution. Therefore, maltose can reduce Fehling's solution and Tollens' reagent.
- �� Option A → Would make maltose non-reducing.
- �� Option B → Hydrolysis is not the reason for reducing behavior.
- �� Option D → Maltose contains no ketonic group.
Used
- Functional Group Analysis
Application:
- Identify the source of reducing behavior.
Final Logic:
- Free anomeric carbon = Reducing sugar.
Maltose = One Free End
19 The exact sequence of the glycosidic linkage in lactose occurs between:
�� Lactose contains galactose and glucose. �� The linkage is β(1→4). �� Galactose C1 joins glucose C4.
Lactose consists of β-D-galactose and β-D-glucose joined through a β(1→4) glycosidic linkage. Specifically, C1 of galactose is linked to C4 of glucose. Hence, Option B is correct.
- �� Option A → Represents sucrose linkage.
- �� Option C → Represents maltose linkage.
- �� Option D → Reverses the actual linkage sequence.
Used
- Direct Recall
Application:
- Recall the linkage pattern of lactose.
Final Logic:
- Lactose = β(1→4) Galactose–Glucose.
Lactose = Gal(1→4)Glu
20 Which specific common name is assigned to lactose due to the environment of its primary natural occurrence?
�� Lactose occurs naturally in milk. �� It is the principal sugar present in milk. �� Therefore it is called milk sugar.
Lactose is the naturally occurring disaccharide found in milk and dairy products. Because of this characteristic occurrence, lactose is commonly known as milk sugar.
- �� Option A → Cane sugar refers to sucrose.
- �� Option B → Invert sugar is obtained from sucrose hydrolysis.
- �� Option D → Malt sugar refers to maltose.
Used
- Direct Recall
Application:
- Recall the common names of disaccharides.
Final Logic:
- Lactose = Milk sugar.
Lactose → Lactation → Milk
