Question

Compound A is a D-aldopentose that can be oxidized to an optically active aldaric acid B. On Kiliani-Fischer chain extension, A is converted into C and D; C can be oxidized to an optically inactive aldaric acid E, but D is oxidized to an optically active aldaric acid F.

What is the structure of compound C?

PLEASE SPECIFY WHAT IS COMPOUND C

Also please take into account the instructions for the answer shown

Compound A is a D-aldopentose that can be oxidized to an optically active aldaric acid B. On Kiliani-Fischer chain extension, A is converted into C and D; C can be oxidized to an optically inactive aldaric acid E, but D is oxidized to an optically active aldaric acid F. What is the structure of compound C? • Use the wedge hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it. • Show stereochemistry in a meso compound. • Do not include lone pairs in your answer. They will not be considered in the grading.

Answer 1

The structures are given below with full explanation:

isomers of D-aldo pentose There which are are four a Сур оно сир 2 HD о» но не ен но н х гг Ноун си, висн, он ен, он / ан, өн the Among and aldaric 4 above isomass will give opticall on onidation. arid нь СЯР оюн Тр1 н нь от нья Вн aboҢ он, он ст, он

After stepping up one carbon atom. by Kilian - fischer reaction and than onidizing to the dicashonghic acid both 3 and 4 will give the following compounds : cool CHO i) Kilian -fischer HOT ہے OH on no . ؟ iton 매 4 Don ہوے A optically optically active active, since both of the aldone ands are optically active this 3 is not Obriously 4 is t which stepping up and deidation one optically active (8) and one optically inactive (E) aldaria aind. LHO L ) Kilian-disclari HOT gire coool H- yo no hyor 4 you cooH E c00 Н optically active a This is optically inactive. contains some

This the structures of a and D are. сно СИО ой Но — и но — нь нот он нь н— ен, он си, он D