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Chapter 28: Q2. (page 1106)

Question: Draw each stereogenic center using a Fischer projection formula.

Short Answer

Expert verified

Answer

(a)

(b)

(c)

(d)

Step by step solution

01

Stereogenic center

The location in a particular molecule where the swap of any two groups leads to a stereoisomer is termed stereogenic centers. They can be present in chiral or achiral molecules

02

Fischer projection formula

Fischer projection formulae are known by another name which is cross formulae. The horizontal bonds are specified as wedges, and the vertical bonds are specified as dashed wedges in a Fischer projection formula.

03

Drawing the stereogenic center using the Fischer projection formula

The molecule is rotated and redrawn to place the horizontal bonds in front of the plane and vertical bonds behind the plane. The vertical bonds are given as dashed wedges, and the horizontal bonds are given as dark wedges. The cross is utilized to indicate the stereogenic center.

a.The Fischer projection formula of compound a can be given as:

Fischer projection formula of compound a

b. The Fischer projection formula of compound b can be given as:

Fischer projection formula of compound b

c. The Fischer projection formula of compound c can be given as:

Fischer projection formula of compound c

d. The Fischer projection formula of compound d can be given as:

Fischer projection formula of compound d

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Most popular questions from this chapter

The most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the 伪 or 尾 anomers of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.

Question: Convert each Haworth projection to its acyclic form.

a.

b.

Draw a stepwise mechanism for the following reaction.

The following isomerization reaction, drawn using D-glucose as starting material, occurs with all aldohexoses in the presence of base. Draw a stepwise mechanism that illustrates how each compound is formed.

A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani-Fischer synthesis, A is converted to two D-aldohexoses, B and C. B is oxidized to an optically inactive aldaric acid. C is oxidized to an optically active aldaric acid. What are the structures of A-C?
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