Concept explainers
(a)
Interpretation:
The observed rotation of the
Concept introduction:
A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. A chiral molecule is an optically active molecule. It rotates the plane of a plane polarized light. The specific optical rotation of a compound is given by the expression as shown below.
Answer to Problem 6.41AP
The observed rotation of the
Explanation of Solution
The molarity of the solution of the
The specific rotation of the
The path length is
The molecular mass of
Therefore, the molar mass of
The specific optical rotation of a compound is given by the expression as shown below.
Where,
•
•
•
The molarity of the solution can be converted into the concentration by multiplying the molar mass of
Rearrange the equation (1) for the value of
Substitute the value of
Therefore, the observed rotation of the
The observed rotation of the
(b)
Interpretation:
The observed rotation of the resultant solution formed by mixture of
Concept introduction:
A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. A chiral molecule is an optically active molecule. It rotates the plane of a plane polarized light. The specific optical rotation of a compound is given by the expression as shown below.
Answer to Problem 6.41AP
The observed rotation of the resultant solution is
Explanation of Solution
The molarity of the solution of the
When
The specific rotation of the
The specific rotations of two enantiomer are same in magnitude and opposite in sign. Therefore, the specific rotation of the
The path length is
The molecular mass of
Therefore, the molar mass of
The specific optical rotation of a compound is given as,
Where,
•
•
•
The molarity of the solution can be converted into the concentration by multiplying the molar mass of
Rearrange the equation (1) for the value of
Substitute the value of
Therefore, the observed rotation of the resultant solution is
The observed rotation of the resultant solution is
(c)
Interpretation:
The enantiomeric excess of the major enantiomer in the corresponding solution is to be calculated.
Concept introduction:
A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. A chiral molecule is an optically active molecule. It rotates the plane of a plane polarized light. The specific optical rotation of a compound is given by the expression as shown below.
Answer to Problem 6.41AP
The enantiomeric excess
Explanation of Solution
The solution formed by mixture of
The percentage of
Where,
•
•
Substitute the value of
The enantiomeric excess of a sample is given as,
Substitute the value of percentage of major enantiomer in the above equation.
Therefore, the enantiomeric excess
The enantiomeric excess
Want to see more full solutions like this?
Chapter 6 Solutions
Organic Chemistry Study Guide and Solutions
- Calculate the units of unsaturation of C6H7NO. And draw out the structure.arrow_forwardDraw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?arrow_forwardConsider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. racemic chiral achiral (1R, 3S) (1R, 3R) (1S, 3S)arrow_forward
- (a) Draw the products of molecular formula C3H4Cl2, including stereoisomers, formed when chlorocyclopropane is heated with Cl2. (b)Assuming that compounds that have different physical properties are separable, how many fractions would be present if the mixture of products were distilled using an efficient fractional distillation? (c) How many fractions would be optically active?arrow_forward12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?arrow_forward(a) What product(s) are formed when the E isomer of C6H5CH = CHC6H5 is treated with Br2, followed by one equivalent of KOH? Label the resulting alkene(s) as E or Z. (b) What product(s) are formed when the Z isomer of C6H5CH = CHC6H5 is subjected to the same reaction sequence? (c) How are the compounds in parts (a) and (b) related to each other?arrow_forward
- Compound X, C8H17Cl, is a chiral product of the radical chlorination of 4-methylheptane.X reacts in SN2 fashion with NaI in acetone to form Z, C8H17I. When the reactant is the R-enantiomer of X, only the R-enantiomer of Z is formed.Draw a structural formula for X; do not show stereochemistry.arrow_forwardTreatment of cyclohexene with C6H5CHI2 and Zn(Cu) forms two stereoisomers of molecular formula C13H16. Draw their structures and explain why two compounds are formed.arrow_forwardDraw the structure(s) of all of the alkene isomers, C5H10, that contain a branched chain. Consider E/Z stereochemistry of alkenes.arrow_forward
- (a) Write the structures of the following compounds and mark them as chiral or achiral. 4 (i) 2-Bromopentane (ii) 3-Bromopentane (iii) 1-Bromo-2-methylbutane (iv) 2-Chloro-3-methylbutane (b) Identify the asymmetric carbon in the chiral compounds. (c) Write the structure of the other enantiomer of the chiral compounds.arrow_forwardGive reasons for the following :(i) Ethyl iodide undergoes SN2 reaction faster than ethyl bromide.(ii) (±) 2-Butanol is optically inactive.(iii) C—X bond length in halobenzene is smaller than C—X bond length in CH3—X.arrow_forwardDQ8.7 Draw the major organic product(s) formed in the following reaction, with the correct stereochemistry. Br HCONa / DMSO C Marvin ISarrow_forward