Sign in
12thPass logo
New chatPYQ LibraryDoubtsRank report
Sign in to see Recents

Your guest activity stays on this device

Sign in to save progress →
Sign in

Basics of Organic Chemistry question

2012 · Shift 1 · Q20
Guest · filters and generic practice availableBrowsing as a guest · PYQ filters and generic practice are available. Sign in only for personalised features and saved progress.
  1. PYQ Library
  2. /JEE Advanced
  3. /Chemistry
  4. /Basics of Organic Chemistry
  5. /2012 · Shift 1 · Q20

Basics of Organic Chemistry question

2012 · Shift 1 · Q20

JEE AdvancedChemistryBasics of Organic ChemistryNumerical+3 / −1
When the following aldohexose exists in its D-configuration, the total number of stereoisomers in its pyranose form is ‾\underline{\hspace{2cm}}​. IIT-JEE 2012 Paper 1 Offline Chemistry - Basics of Organic Chemistry Question 20 English
Numerical answer
View written solutionFree

Correct answer: 16

  1. Identify the stereochemical features of an aldohexose

An aldohexose has the open-chain structure:

CHO−(CHOH)4−CH2OH\text{CHO}-(\text{CHOH})_4-\text{CH}_2\text{OH}CHO−(CHOH)4​−CH2​OH

So, in the open-chain form, the stereogenic centers are at:

C2,C3,C4,C5C_2, C_3, C_4, C_5C2​,C3​,C4​,C5​

That means there are 4 chiral centers in the open-chain aldohexose.

  1. What does D-configuration fix?

For sugars, D/L is determined by the configuration at the last chiral carbon (here C5C_5C5​).

So if the aldohexose is specified to be in its D-configuration, then the configuration at C5C_5C5​ is fixed.

Thus, among the 4 original chiral centers:

  • C5C_5C5​ is fixed,
  • C2,C3,C4C_2, C_3, C_4C2​,C3​,C4​ can vary.

Hence the number of possible open-chain D-aldohexoses is:

23=82^3 = 823=8

  1. Conversion to pyranose form

In pyranose formation, the aldehyde group at C1C_1C1​ reacts with the hydroxyl group at C5C_5C5​ to form a cyclic hemiacetal.

This creates a new stereocenter at the anomeric carbon C1C_1C1​.

For each open-chain D-aldohexose, there are therefore 2 anomers:

  • α\alphaα
  • β\betaβ

So total stereoisomers in pyranose form:

8×2=168 \times 2 = 168×2=16

  1. Final answer

Therefore, the total number of stereoisomers in the pyranose form of a D-aldohexose is:

16\boxed{16}16​

  1. Comparison with stored correct answer

Stored correct answer = 888

My derived answer = 161616

The stored answer appears to have counted only the D-aldohexoses in open-chain form and did not include the additional anomeric stereocenter formed in the pyranose ring.

Hence, I disagree with the stored answer.

PreviousNext

More from Basics of Organic Chemistry

  • Which of the given statement(s) about N, O, P and Q with respect to M is(are) correct? Includes diagram2012 · Multiple correct
  • Among the given options, the compound(s) in which all the atoms are in one plane in all the possible conformations (if any) is(are)2011 · Multiple correct
  • Among the following compounds, the most acidic is2011 · MCQ
  • The total number of contributing structure showing hyper-conjugation (involving C-H bonds) for the following carbocation is ​. Includes diagram2011 · Numerical
  • In the Newman projection for 2,2-dimethylbutane, X and Y can, respectively, be Includes diagram2010 · Multiple correct
  • The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4​H6​ is2010 · Numerical
  • The correct statement(s) about the compound H3​C(HO)HC−CH=CH−CH(OH)CH3​  (X) is (are)2009 · Multiple correct
  • The correct acidity order of the following is Includes diagram2009 · MCQ