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Classification of Pyranose Ring Carbohydrate Structure

The following carbohydrate is

Diagram 0

Options

A

a ketohexose

B

an aldohexose

Correct
C

an α\alpha-furanose

D

an α\alpha-pyranose

Topics & Concepts

Step-by-Step Solution

To determine the classification of the given carbohydrate, we analyze its chemical structure step-by-step:

  1. Identification of Ring Size:

    • The ring contains 55 carbon atoms and 11 oxygen atom, forming a six-membered ring known as a pyranose ring. Thus, it cannot be a furanose (a five-membered ring), which eliminates Option C.
  2. Analysis of the Anomeric Carbon (C-1):

    • The anomeric carbon (C-1) is bonded to a hydroxyl group (−OH-\text{OH}), a hydrogen atom (−H-\text{H}), C-2, and the ring oxygen atom (−O−-\text{O}-).
    • In a ketohexose (such as D-fructose in its cyclic form), the anomeric carbon (C-2) is attached to a hydroxymethyl group (−CH2OH-\text{CH}_2\text{OH}) instead of a single hydrogen atom.
    • The presence of a hydrogen atom (−H-\text{H}) directly attached to the anomeric carbon indicates that the original open-chain form contained an aldehyde functional group (−CHO-\text{CHO}) at the C-1 position. This confirms that it is an aldose.
  3. Counting the Total Number of Carbon Atoms:

    • The ring contains 55 carbon atoms (C-1, C-2, C-3, C-4, C-5).
    • An additional exocyclic carbon atom is present in the −CH2OH-\text{CH}_2\text{OH} group attached to C-5.
    • Total number of carbon atoms = 5+1=65 + 1 = 6.
    • A carbohydrate with 6 carbon atoms is classified as a hexose.
  4. Anomeric Configuration (α\alpha vs β\beta):

    • Looking at the relative positions of the groups at the reference carbon (C-5) and the anomeric carbon (C-1):
      • The exocyclic −CH2OH-\text{CH}_2\text{OH} group at C-5 points upwards.
      • The anomeric −OH-\text{OH} group at C-1 also points in the same relative direction (cis/β\beta-configuration).
    • Therefore, it is a β\beta-anomer, making Option D (α\alpha-pyranose) incorrect.

Combining the aldose functionality and the 6-carbon hexose framework, the carbohydrate is an aldohexose.

Correct Answer: B