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Question 53 of 65

Q.Draw the structure of Fructose. Mention the number of Chiral Carbon atoms and number of optical isomers present in it.

Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2019Subjective· 3mImportance★★★★★
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Figure — The stem asks to draw the structure of fructose and count its chiral carbons; the catalog D-fructose open-chai
Figure — The stem asks to draw the structure of fructose and count its chiral carbons; the catalog D-fructose open-chai

Fructose, an open-chain 2-ketohexose, has 3 chiral carbons and therefore 23=82^3=8 possible optical isomers.

Open-chain structure of fructose (C6H12O6C_6H_{12}O_6, a ketohexose):

C1: CH2OHC2: C=O(keto group)C3: H−C−OHC4: HO−C−HC5: H−C−OHC6: CH2OH\begin{aligned} &C1:\ CH_2OH \\ &C2:\ C{=}O \quad (\text{keto group}) \\ &C3:\ H-C-OH \\ &C4:\ HO-C-H \\ &C5:\ H-C-OH \\ &C6:\ CH_2OH \end{aligned}

written linearly as CH2OH−CO−CHOH−CHOH−CHOH−CH2OHCH_2OH-CO-CHOH-CHOH-CHOH-CH_2OH.

Locating the chiral carbons: A carbon is chiral (asymmetric) if it is bonded to four different groups. C1 (CH2OHCH_2OH, bonded to C2 which bears the keto group) and C2 (the carbonyl carbon, only 3 groups, sp2sp^2) are not chiral. C6 (CH2OHCH_2OH, terminal) is also not chiral. Carbons C3, C4 and C5, however, are each bonded to an −H-H, an −OH-OH, and two different carbon-chain fragments (one side leading towards the keto/C1 end, the other towards the terminal CH2OHCH_2OH/C6 end) - so each of these three is a genuine chiral centre.

Number of chiral carbons = 3.

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