The specific rotation of a sample of mandelic acid [PhCH(OH)CO2H] is +12.5° and of pure R-(+)- mandelic acid is +158°. Calculate the (1) % optical purity, (2) ee, (3) % composition and (4) draw a clear stereo-structure for the enantiomer in excess

The specific rotation of a sample of mandelic acid [PhCH(OH)CO2H] is +12.5° and of pure R-(+)- mandelic acid is +158°. Calculate the (1) % optical purity, (2) ee, (3) % composition and (4) draw a clear stereo-structure for the enantiomer in excess

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.59P

See similar textbooks

Related questions

Q: 160 °C + 24h

Q: The following sterol reacts with excess 1)BH3 and 2)H202/OH¯ which converts both double bonds.…

A: The double bonds show addition reaction when treated with diborane in the presence of H2O2/OH-.

Q: The separate enantiomers. of 2-hydroxyheptanoic acid were needed for determination of the absolute…

A: Given reagent is (R) or (S)-malic acid.

Q: Using the Cahn–Ingold–Prelog sequence rules, assign priorities to the groups around the chiral…

A: Cahn–Ingold–Prelog sequences rules allow us to assign priority to different substituents. The first…

Q: What is the stereoisomeric composition of a mixture of 2-bromobutanes, with 50%ee of…

A: Solution In stereochemistry, stereoisomerism, or spacial state, may be a type of state within which…

Q: Using Cahn-Ingold-Prelog rules, rank these substituents from highest priority to lowest priority. II…

Q: The structure shown below is that of one of the geometric isomers (the E- isomer) of the…

A: In the given question a molecule is given and it is asked that why this is assigned as E-isomer.…

Q: A student has isolated a chiral alkyl halide (shown below) with a specific rotation of [a] 22.1º.…

A: The question is based on the concept of organic reactions. we have to identify the product formed…

Q: Draw the structural formula of the major product of the reaction of (S)-2,2,3-trimethyloxirane with…

A: Step 1: The reactant that is given to us is epoxide and when there is an unsymmetrical epoxide…

Q: Many studies have shown that one specific enantiomer of citalopram (“S”) is the one capable of…

A: A chemical substance, called serotonin, present inside the human, helps to control the mood and…

Q: Describe the stereochemistry of the bromohydrin formed in trans-3-Hexene 1 Br2/H2O reaction (…

A: When alkenes react with bromine in aqueous medium, electrophilic addition takes place. The double…

Q: 1. how many stereoisomers are possible for 9,10- dibromo hexadecanoic acid? 2. Addition of bromine…

A: 1- To calculate the number of stereoisomers in a compound, first find the number of chiral centers…

Q: ) Why would an unstabilized vlide tend to form more of the Z-stereoisomer?

Q: Tobacco smoke from a typical cigarette contains 20-40 ng of benzo[a]pyrene, which can be oxidized by…

A: Welcome to bartleby! We have to find out compound A

Q: Why is there a need to wash the residue (which could be CaC2O4) twice with water before the addition…

A: Answer - According to the question - The washed liquid must be a substance which does not interfere…

Q: Draw the structure of (2R, 35)-2,3-dichloropentane. Take particular care to indicate three-…

A: Stereochemistry is a branch of chemistry that deals with the study of relative 3D-arrangement of…

Q: Describe the stereochemistry of the bromohydrin formed in cis-3-Hexene 1 Br2/H2O reaction (…

A: This cis and trans is configurational geometric isomerism–trans isomerism in organic chemistry. The…

Q: A chemist finds that the addition of (+)@epinephrine to the catalytic reduction of butan2-one gives…

A: Enantiomeric excess: The excess percentage of one of the enantiomer in a sample of enantiomeric pair…

Q: Explain how you could seperate a pair of enantiomers, consider a racemic mixture of…

A: The most commonly used procedure for separating enantiomers is to convert them to a mixture of…

Q: What are the absolute configurations of the stereogenic centers in the following molecule: B C. Draw…

Q: Determine the percent composition of both enantiomers of a mixture of butanol, with an observed…

Q: Predict the IR absorption bands (peaks) observed in the spectrum of p-anisaldehyde.

A: The interaction between electromagnetic radiation and compound is called spectroscopy IR…

Q: Treatment of either anomer of fructose with excess ethanol in the presence of a trace ofHCl gives a…

A: Epimers are the stereoisomers in which the configuration differs at only one stereogenic center.…

Q: What are the stereochemical configurations of the two diastereomers of (2S,4S)-2,4-hexanediol? Write…

Q: . In the bromination of stilbene experiment, trans-stilbene (E-stilbene) is used. If cis-stilbene…

A: Applying RS configuration for determining stereochemistry of products.

Q: Which of the following distinguished scientists is correctly identified? There may be more than one…

A: Stereochemistry is branch of chemistry that tells the three dimensional arrangement of atoms in…

Q: Compound C undergoes a chemical reaction with a reagent, resulting in the formation of two new…

A: Hello. Since your question has multiple sub-parts, we will solve the first three sub-parts for you.…

Q: 1) Rationalize the region-selectivity of the following addition reactions ے والا

A: Markovnikov's rule: when an asymmetrical reagent is added to an asymmetrical alkene, the negative…

Q: Which of the following distinguished scientists is correctly identified? There may be more than one…

A: The importance of ring strain was proposed by the scientist Adolf von Baeyer and is called Baeyer…

Q: Show hoe the Cahn-Ingold-Prelog sequence rules are used to assign the configuration of the…

A: Cahn-Ingold-Prelog rules are used to assign configuration to a chiral carbon in a molecule. A chiral…

Q: 2. Carefully draw the structures of the models that you have made using proper stereochemical…

A: Isomers having non- superimpossible mirror image relationship, called enantiomers. Isomers having…

Q: Which of the following distinguished scientists is correctly identified? There may be more than one…

A: Adolf von Baeyer in 1885 gave the strain theory for cyclic compounds. He said more the angle of…

Q: The chiral hydroxyl compound P, C7H14O contains a five-membered ring and shows positive result in…

A: This question is related to finding out the structures of unknown compounds involving specific type…

Q: Vigorous oxidation of the following bicycloalkene breaks the carbon-carbon double bond and converts…

A: The given oxidation reaction is,

Q: What are the stereochemical configurations of the two diastereomers of (2R,4R)-2,4-hexanediol? Write…

A: Diastereomers are the type of stereoisomers which has change in the spatial arrangement on only one…

Q: Clopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in…

A: Treatment of carboxylic acid with alcohols in the presence of strong acid yields esters. Compound A…

Q: what is the stereochemistry involved in the rducing benzil experiment. And write the definition and…

Q: Compound K, L and M are three isomers with the molecular formula C5H10O. Compound K cannot be…

A: Answer:- This question is answered by using the simple concept of chemical reaction of organic…

Q: Draw the structure of (1R, 25, 35)-1,2-dibromo-3-ethylcyclohexane. Take particular care to indicate…

A: Given IUPAC name is (1R,2S,3S)-1,2-dibromo-3-ethylcyclohexane. Observing the name shows that 2 Br…

Q: Complete the following Grignard reaction. The starting material is chiral and present as a single…

Q: Are the compound names below representative of prochiral or not prochiral molecules? Label them…

A: In stereochemistry, prochiral molecules are those that can be converted from achiral to chiral in a…

Q: (b) The reaction (R)-2-chloro-3-methylbutane with KOH shown below, resulted in a mixture of three…

Q: Which compound(s) in spearmint oil do you expect will be visible on the TLC plate under UV…

A: The main components in spearmint oil are R-carvone, R-limonene and (1R,2R,4R)-dihydrocarveol.

Question

The specific rotation of a sample of mandelic acid
[PhCH(OH)CO2H] is +12.5° and of pure R-(+)-
mandelic acid is +158°. Calculate the (1) % optical
purity, (2) ee, (3) % composition and (4) draw a clear
stereo-structure for the enantiomer in excess

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 2 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

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

The structure of A is shown below. HO 3 -CH2CH=CH2 A (i) Predict the possible number of stereoisomers A can have. (ii) Draw the 3D structure of the (25, 3R, 5S) enantiomer showing its correct stereochemistry. (iii) Calculate the specific rotation of each enantiomer in a mixture containing 10 mL (0.10 M) of (2S, 3R, 55) enantiomer and 30 mL (0.10 M) of (2R, 3S, 5R) enantiomer. Given the specific rotation of the mixture = +4.8°.
The chiral hydroxyl compound P, C7H14O contains a five-membered ring and showspositive result in iodoform test. Compound P and sodium bromide can be produced byrefluxing compound Q with aqueous NaOH solution. Compound P is heated withbenzoic acid in the presence of concentrated H2SO4 to form a sweet-smelling product,compound R. Deduce the structure of P, Q and R. PLEASE PROVIDE CLEAR HAND WRITING AND SOLUTIONS
The specific rotation of (S)-carvone (at 20 degrees) is +61. A chemist prepared a mixture of (R)-carvone and its enantiomer, and this mixture had an observed rotation of -55. (a) What is the specific rotation of (R)-carvone at 20 degrees? (b) What percentage of the mixture is (S)- carvone? Choose from the following options. 1. 90% (S)-carvone and 10% (R) 2. 10% (S)-carvone and 90% (R) 3. 95% (S)-carvone and 5% (R) 4. 5% (S)- carvone and 95% (R)
The specific rotation of (S)-carvone (at 20 degrees) is +61. A chemist prepared a mixture of (R)-carvone and its enantiomer, and this mixture had an observed rotation of -55. (a) What is the specific rotation of (R)-carvone at 20 degrees?
Answer ALL parts of this question. The structure shown below is that of one of the optical isomers of the well-known analgesic, ibuprofen: (a) (b) (c) CH₂ H₂C-A C H₂ 2048 ÇO,H CH CH₂ Explain how the Cahn Ingold Prelog sequence rules can be used to rank groups in order of priority, using the four groups attached to the chiral centre in ibuprofen as illustrated. Based on the order of priority of the four groups determined in part (a) of this question, explain which of the two enantiomers (R or S) of ibuprofen is shown. S Draw the structure of the enantiomer of this compound and comment on why it might produce a different reaction in vivo (in fact the enantiomer has no analgesic effect).
3b) (i) Using Fischer projection, draw all the stereoisomers of 3-chloro-2-hydroxypentanoic acid. ii) Assign the chiral centre(s) with R/S configurations in part (b)(i). Indicate which areenantiomers, diastereomers and meso compounds (if any).
The anti-inflammatory agent, (S)-naproxen sodium salt has a specific rotation of +66°. The commercial preparation of the latter agent results in a mixture that has a 97% enantiomeric excess (ee). Na Hooooja moo (S)-naproxen sodium salt (d) What percentage of each enantiomer is obtained from the above commercial mixture? H3CO (e) Provide a reaction scheme for the formation of the (S)-naproxen sodium salt from "acidic" (S)-naproxen.
Answer ALL parts of this question. Fluoxetine (Prozac) is an anti-depressant, sold as a racemic mixture with both enantiomers of equal activity. (S)-Fluoxetine has a specific optical rotation of +14.0°. F₂C. HO (S)-Fluoxetine (c) A laboratory mixture has 80% enantiomeric excess (ee) of (S)-fluoxetine. What percentage of each enantiomer is present in the mixture? (d) What is the observed specific rotation of the laboratory mixture in part (c)? (e) Draw the product of HCI reaction with (S)-fluoxetine.
8. The specific rotation of (S)-carvone (at +20°C) is +61. A chemist prepared a mixture of (R)-carvone and its enantiomer, and this mixture had an observed rotation of -55°. (a) What is the specific rotation of (R)-carvone at 20°C? (b) Calculate the % ee of this mixture. (c) What percentage of the mixture is (S)-carvone?
A sample of (S)-(+)-lactic acid was found to have an enantiomeric excess of 72%. How much R isomer is present in the sample?
Treatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.
Thalidomide exists in two enantiomeric isomers as shown below. N (R) NI(S) O If a solution is prepared by adding a 50:50 ratio of two enantiomers what will be the expected observed rotation? Explain your answer in 1-2 sentences.