ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582422
Author: Brown
Publisher: CENGAGE L
expand_more
expand_more
format_list_bulleted
Textbook Question
Chapter 21, Problem 21.11P
Molecules of 6,6′-dinitrobiphenyl-2,2′-dicarboxylic acid have no tetrahedral chiral center, and yet they can be resolved to a pair of enantiomers. Account for this chirality.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Molecules of 6,6'-dinitrobiphenyl-2,2'-dicarboxylic acid have no tetrahedral chiral
center, and yet they can be resolved to a pair of enantiomers. Account for this chirality.
СООН
НООС NO2
6,6'-Dinitrobiphenyl-2,2'-dicarboxylic acid
A chemist synthesized compound X as a racemic mixture. When the ketone group in X was
enzymatically reduced to the corresponding alcohol, a 100% yield was obtained of the product
shown below. Choose the statement that best describes this result.
ОН
enzyme
C;H1
`OCH,CH;
pH 4.0
C3H1
`OCH,CH3
ОН
ÕH
X (racemic)
(100% yield)
One enantiomer of compound X reacts quickly with the enzyme. The other enantiomer of compound X is
unreactive, but rapidly equilibrates with the reactive enantiomer under the reaction conditions.
Since compound X was racemic, it makes sense that only a single product was obtained.
O The product is a meso compound, so either enantiomer of compound X gives the same product.
One enantiomer of compound X reacts quickly with the enzyme, while the other enantiomer of compound X
remains unchanged.
Please explain it. ASAP
Chapter 21 Solutions
ORGANIC CHEMISTRY-OWL V2 ACCESS
Ch. 21.2 - Construct a Frost circle for a planar...Ch. 21.2 - Which compound gives a signal in the 1H-NMR...Ch. 21.2 - Prob. 21.3PCh. 21.2 - Prob. 21.4PCh. 21.3 - Prob. 21.5PCh. 21.4 - Arrange these compounds in order of increasing...Ch. 21.4 - Prob. AQCh. 21.4 - Prob. BQCh. 21.4 - Prob. CQCh. 21.5 - Prob. 21.7P
Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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
- Draw the correct structure(s) for (2R,3S)-2,3-dibromobutane. Show stereochemistry clearly. explicitly draw all four groups, including wedge/dash bonds, around a chirality center. Indicate whether the compound(s) could exist in an optically active form.arrow_forwardWhich of the following compounds are capable of being resolved into enantiomers?(a) N-ethyl-N-methylaniline (b) 2-methylpiperidine (c) 1-methylpiperidine (d) 1,2,2-trimethylaziridinearrow_forwardDraw a diastereomer of (2R,3R)-2,3-dibromobutanedioic acidarrow_forward
- Much of our understanding of conformational analysis has arisen from studies on the reactions of rigid steroid nuclei. For example, the concept of trans-diaxial ring opening of epoxycyclohexanes was proposed to explain the stereoselective reactions seen with steroidal epoxides. Predict the product when each of the following steroidal epoxides is treated with LiAlH4.arrow_forwardGiven the Ka values (in parentheses) for the following acids: HSO4– (Ka= 1.2 x 10–2); HNO2 (Ka= 4.0 x 10–4); HC2H3O2 (Ka= 1.8 x 10–5); Calculate Kc values for the following acid-base equilibria: (a) HSO4–(aq) + C2H3O2–(aq) ⇌ HC2H3O2(aq) + SO42–(aq) (b) HC2H3O2(aq) + NO2–(aq) ⇌ HNO2(aq)+ C2H3O2–(aq)arrow_forwardPlease draw the skeletal formula of the following compounds: (A) Isobutyraldehyde (B) α-Ethyl-γ-methoxycaproaldehyde (C) 6-Hydroxyhexanal (D) 2,4-Pentanedione (E)3-Cyano-7-oxoheptanoic acidarrow_forward
- Give two names for the following compound:arrow_forwardArrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenolarrow_forwardMuch of our understanding of conformational analysis has arisen from studies on the reactions of rigid steroid nuclei. For example, the concept of trans-diaxial ring opening of epoxycyclohexanes was proposed to explain the stereoselective reactions seen with steroidal epoxides. Predict the product when each of the following steroidal epoxides is treated with LiAlH4.arrow_forward
- Look up the structure of lisdexamfetamine (Vyvanse), a drug used in the treatment of attention deficit hyperactivity disorder (ADHD). Redraw it and identify all the functional groups present. What is known about itstherapeutic properties?arrow_forwardWrite the structure of following organic compoundarrow_forward(a) How many Stereoisomers are possible for 9,10- dibromoexadecanoic acid?(b) Addition of bromine to palmitoleic acid primarily yields a set of enantiomers, (±) -three-9,10-dibromohexadecanoic acid. The addition of bromine is an anti-addition to the double bond (ie, it appears to occur through the intermediary of the bromonium ion). Taking into account the stereochemistry of the cis double bond of palmitoleic acid and the stereochemistry of adding bromine,Write a three-dimensional structure for (±) -three-9,10-dibromohexadecanoic acid!arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
07 Physical Properties of Organic Compounds; Author: Mindset;https://www.youtube.com/watch?v=UjlSgwq4w6U;License: Standard YouTube License, CC-BY