Exam 5: Stereochemistry at Tetrahedral Centers

A compound with specific rotation,[α]_D = +35.4° reacts to form a single product.The product of the reaction shows no optical activity.This could mean that the product:

_____ is an atom in a molecule that is bonded to four different atoms or groups of atoms.

Draw a Newman projection of the most stable conformation of (2R,3S)-dibromobutane sighting down the C2−C3 bond.

Estriol,a potent estrogenic hormone,has been isolated from the urine of pregnant women.When 40 mg of estriol is dissolved in 1.0 mL of dioxane and placed in a sample tube with 1 dm path length a rotation of +2.32° is observed.Calculate the specific rotation for estriol.

Which of the following objects is not chiral?

Draw a wedge-dash projection of (2R,3S)-dibromobutane.

The specific rotation of a compound is denoted by the symbol:

Draw a structure for a singly substituted chiral chloroalkane that contains four carbon atoms.Indicate the chirality center with an asterisk (*).

Exhibit 5-5 Label each pair of stereoisomers below as: -_____

Acetoacetate synthase catalyzes the addition of pyruvate to β-ketobutyrate to yield α-aceto-α-hydroxybutyrate.If the addition occurs from the si face of β-ketobutyrate,what is the stereochemistry of the product?

Exhibit 5-3 Assign R,S configurations to each indicated chirality center in the molecules below. ​ -Refer to Exhibit 5-3.The configuration of this carbon atom (D) is _____.

Exhibit 5-6 Refer to the structure below to answer the following question(s). ​ -Refer to Exhibit 5-6.(S)-(−)-Serine:

Exhibit 5-4 Consider the structure of streptimidone to answer the following question(s). ​ -Refer to Exhibit 5-4.Based on the number of chirality centers,how many stereoisomers of streptimidone are possible?

In which of the following groups can the carbon atom be a chiral center?

Which of the following compounds will rotate the plane of polarized light?

Exhibit 5-7 A natural product having [α]_D = +40.3° has been isolated and purified. -Refer to Exhibit 5-7.This information indicates that the natural product:

Exhibit 5-5 Label each pair of stereoisomers below as: -_____

Exhibit 5-3 Assign R,S configurations to each indicated chirality center in the molecules below. ​ -Refer to Exhibit 5-3.The configuration of this carbon atom (C) is _____.

Exhibit 5-5 Label each pair of stereoisomers below as: -_____

Exhibit 5-6 Refer to the structure below to answer the following question(s). ​ -Refer to Exhibit 5-6.Give the complete name of the enantiomer of (S)-(−)-serine.