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Analytical Chemistry — SpectroscopyIChO

1,3-Dihydroxyacetone can be converted to glyceraldehyde. On standing this glyceraldehyde changes spoAnalytical Chemistry — Spectroscopy Chemistry Question

1,3-Dihydroxyacetone can be converted to glyceraldehyde. On standing this glyceraldehyde changes spontaneously into a six member cyclic dimer C6H12O6. The infrared spectrum of the dimer shows no absorption peak between 1600 – 1800 cm-1 and the dipole moment of the dimer is determined to be zero.

3.1.

Write the Fischer projection structural formula(e) for the resulting glyceraldehyde and indicate configuration using D(+) and/or L(-).

3.2.

Write the structural formula for the reaction intermediate of the conversion of 1,3-dihydroxyacetone to glyceraldehyde.

3.3.

Write the structural formula for the dimer.

3.4.

Using Haworth projection formula represent the possible stereoisomers which fit the dipole moment data.

3.5.

Denote each chiral carbon atom in the above formulae with R or S.

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