JEE Advanced 2015 · Paper 1 · Chemistry Q32

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ChemistryMultiple correct+4 / -2Question 32 of 60

The structure of D-(+)-glucose is shown (Fischer projection: CHO at top; OH on the right, left, right and right at C2, C3, C4 and C5; CH₂OH at the bottom).

The structure of L-(−)-glucose is

D-(+)-Glucose in Fischer projection: CHO at top; at C2 to C5 the OH groups point right, left, right, right; CH₂OH at bottom.

Fischer projection: CHO at top, CH₂OH at bottom; OH on the left, right, left and left at C2, C3, C4 and C5 respectively.

Fischer projection: CHO at top, CH₂OH at bottom; OH on the right, left, right and left at C2, C3, C4 and C5 respectively.

Fischer projection: CHO at top, CH₂OH at bottom; OH on the left, left, right and left at C2, C3, C4 and C5 respectively.

Fischer projection: CHO at top, CH₂OH at bottom; OH on the left, left, left and right at C2, C3, C4 and C5 respectively.

Answer and worked solution

Official answer: A

L-(−)-Glucose is the mirror image of D-(+)-glucose, so every stereocentre is inverted. In the Fischer projection, the OH pattern changes from right, left, right, right to left, right, left, left.

(A)

Topics:Carbohydrates Optical isomerism and chirality

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JEE Advanced 2015 · Paper 1, Chemistry question 32