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4-Hydroxy- and 5-hydroxyaldehydes exist primarily as

Chapter 21, Problem 19P

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QUESTION:

Problem 19P

4-Hydroxy- and 5-hydroxyaldehydes exist primarily as cyclic hemiacetals. Draw the structure of the cyclic hemiacetal formed by each of the following:

a. 4-hydroxybutanal b. 4-hydroxypentanal c. 5-hydroxypentanal d. 4-hydroxyheptanal

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QUESTION:

Problem 19P

4-Hydroxy- and 5-hydroxyaldehydes exist primarily as cyclic hemiacetals. Draw the structure of the cyclic hemiacetal formed by each of the following:

a. 4-hydroxybutanal b. 4-hydroxypentanal c. 5-hydroxypentanal d. 4-hydroxyheptanal

ANSWER:

Solution 19P

 (a)

4-hydroxybutanal has the OH group at the 4th position with respect to the aldehyde group. So a five membered cyclic hemiacetal will be formed.

(b)

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