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

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter12: Chirality
Section: Chapter Questions
Problem 15E
icon
Related questions
icon
Concept explainers
Question
Compound A is a D-aldopentose that can be oxidized to an optically inactive aldaric acid B. On Kiliani-Fischer chain extension, A is
converted into C and D; C can be oxidized to an optically active aldaric acid E, but D is oxidized to an optically inactive aldaric acid
F.
What is the structure of compound F?
• 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.
Transcribed Image Text:Compound A is a D-aldopentose that can be oxidized to an optically inactive aldaric acid B. On Kiliani-Fischer chain extension, A is converted into C and D; C can be oxidized to an optically active aldaric acid E, but D is oxidized to an optically inactive aldaric acid F. What is the structure of compound F? • 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.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Carbohydrates
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:
9781305446021
Author:
Lampman
Publisher:
CENGAGE LEARNING - CONSIGNMENT