Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 5, Problem 60P
Interpretation Introduction
Interpretation: The method of resolving racemic 1-phenylethanamine into diastereomers using the reversible conversion into diastereomers needs to be explained.
Concept Introduction: To break the compound into diastereomers, react the compound to a pure agent which can break the compound.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
For following substituted benzenes:
[1] C6H5Br; [2] C6H5CN; [3] C6H5OCOCH3:
Does the substituent activate or deactivate the benzene ring inelectrophilic aromatic substitution?
Gamma(y)-amino butyric acid (GABA) is a neurotransmitter (a chemical that is used to send signals from one neuron to another) of the
mammalian central nervous system. In order to understand how GABA works, conformationally restricted analogues, such as
compound 1, have been made. During a synthesis of compound 1, compound 2 was subjected to allylic bromination using NBS and a
radical initiator (AIBN) instead of light (Aust. J. Chem. 1981, 34, 2231-2236).
H₂N.
CH3
GABA
CO₂H
CH3
dddd
CH3
H₂N
Modify the structures given below to draw all eight possible allylic bromides that can be formed when compound 2 undergoes allylic
bromination, considering all possible regiochemical and stereochemical outcomes. You can use the single bond tool to add/remove pi
bonds.
CH3
CO₂H
CH3
solddd
CH3
CH3
2
CH₂
CO₂Et
A chiral amine A having the R configuration undergoes Hofmann elimination to form an alkene B as the major product. B is oxidatively cleaved with ozone, followed by CH3SCH3, to form CH2 = O and CH3CH2CH2CHO. What are the structures of A and B?
Chapter 5 Solutions
Organic Chemistry: Structure and Function
Ch. 5.1 - Prob. 5.3ECh. 5.1 - Prob. 5.4ECh. 5.1 - Prob. 5.5ECh. 5.2 - Prob. 5.6ECh. 5.2 - Prob. 5.8TIYCh. 5.3 - Prob. 5.9ECh. 5.3 - Prob. 5.11TIYCh. 5.3 - Prob. 5.12ECh. 5.4 - Prob. 5.13ECh. 5.4 - Prob. 5.14E
Ch. 5.4 - Prob. 5.16TIYCh. 5.4 - Prob. 5.17ECh. 5.5 - Prob. 5.18ECh. 5.5 - Prob. 5.19ECh. 5.5 - Prob. 5.20ECh. 5.6 - Prob. 5.21ECh. 5.6 - Prob. 5.22ECh. 5.6 - Prob. 5.23ECh. 5.7 - Prob. 5.24ECh. 5.7 - Prob. 5.26TIYCh. 5.7 - Prob. 5.27ECh. 5 - Prob. 5.1ECh. 5 - Prob. 5.2ECh. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Prob. 36PCh. 5 - Prob. 37PCh. 5 - Prob. 38PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - Prob. 41PCh. 5 - Prob. 42PCh. 5 - Prob. 43PCh. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - Prob. 48PCh. 5 - Prob. 49PCh. 5 - Prob. 50PCh. 5 - Prob. 51PCh. 5 - Prob. 52PCh. 5 - Prob. 53PCh. 5 - Prob. 54PCh. 5 - Prob. 55PCh. 5 - Prob. 56PCh. 5 - Prob. 57PCh. 5 - Prob. 58PCh. 5 - Prob. 59PCh. 5 - Prob. 60PCh. 5 - Prob. 61PCh. 5 - Prob. 62PCh. 5 - Prob. 63PCh. 5 - Prob. 64PCh. 5 - Prob. 65PCh. 5 - Prob. 66PCh. 5 - Prob. 67PCh. 5 - Prob. 68PCh. 5 - Prob. 69PCh. 5 - Prob. 70PCh. 5 - Prob. 71P
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
- Please explain properly. Q16. Ibuprofen, an example of an NSAID, is the active ingredient in several popular over-the-counter analgesics in the U.S., and it is sold in racemic form, even though only the S-enantiomer is pharmacologically active. Suggest methods that might be used to obtain or prepare ibuprofen in enantiomerically pure form, based on processes and reactions you learned. H CH3 (CH3)2CHCH₂ S-ibuprofen CO₂Harrow_forwardHow many degrees of unsaturation (or DBE) are present in (2E,6E)-2,6-Bis(4-methoxybenzylidene)cyclohexanone?arrow_forward(c) The sedative, R-thalidomide, was once used to address symptoms of morning sickness in expectant mothers, however, when it was discovered that S- thalidomide causes deformities in infants, the use of R-thalidomide as a sedative was discontinued. With the help of a reaction mechanism, explain why enantiopure R-thalidomide can not be safely used as a sedative without affecting infantsarrow_forward
- (d) When a primary amine is combined with a ketone, both an imine and an enamine can be obtained. With most ketones, the major product is the imine, as shown: H3C NH2 -N -CH3 -CH3 imine: major product enamine: minor product However, in some cases, like the one shown below, the major product is the enamine. CO₂Et CO₂Et CO₂Et H H3C NH2 -CH3 imine: minor product -CH3 enamine: major product Referring to specific features of the starting materials, intermediates, or products, explain why.arrow_forwardIs it possible to distinguish between the following compounds using the spectroscopic techniques covered in CHE331? If so, discuss how. If not, discuss why.Benzonitrile vs Benzaldehyde(a) UV spectroscopy(b) IR spectroscopy(c) Mass spectrometry(d) 13C NMR spectroscopy(e) 1H NMR spectroscopyarrow_forwardCompound A is first reacted with methylamine in the presence of acid and then treated with NaBH3CN. Using the spectroscopic data given, what is the structure of the product after step 1?arrow_forward
- 1. Draw structures corresponding to the following names:(a) Bromoacetone(b) (S)-2-Hydroxypropanal(c) 2-Methyl-3-heptanone(d) (2S,3R)-2,3,4-Trihydroxybutanal(e) 2,2,4,4-Tetramethyl-3-pentanone(f) 4-Methyl-3-penten-2-one(g) Butanedial(h) 3-Phenyl-2-propenal(i) 6,6-Dimethyl-2,4-cyclohexadienone(j) p-Nitroacetophenone 2. How would you prepare the following substances from 2-cyclohexenone? More than onestep may be needed.(a) Cyclohexene(b) 3-Phynylcyclohexanone(c) 3-Oxocyclohenanecarboxylic acid(d) Methylcyclohexanearrow_forward1. Draw structures corresponding to the following names:(a) Bromoacetone(b) (S)-2-Hydroxypropanal(c) 2-Methyl-3-heptanone(d) (2S,3R)-2,3,4-Trihydroxybutanal(e) 2,2,4,4-Tetramethyl-3-pentanone(f) 4-Methyl-3-penten-2-one(g) Butanedial(h) 3-Phenyl-2-propenal(i) 6,6-Dimethyl-2,4-cyclohexadienone(j) p-Nitroacetophenonearrow_forward(a) Give a plausible explanation for each one of the following :(i) There are two – NH2 groups in semicarbazide. However, only one such group is involved in the formation of semicarbazones.(ii) Cyclohexanone forms cyanohydrin in good yield but 2, 4, 6-trimethylcyclohexanone does not.(b) An organic compound with molecular formula C9H10O forms 2, 4, – DNP derivative, reduces Tollens’ reagent and undergoes Cannizzaro’s reaction. On vigorous oxidation it gives 1, 2-benzene-di- carboxylic acid. Identify the compound.arrow_forward
- 1. Draw structures corresponding to the following names: (a) Bromoacetone (b) (S)-2-Hydroxypropanal (c) 2-Methyl-3-heptanone (d) (2S,3R)-2,3,4-Trihydroxybutanal (e) 2,2,4,4-Tetramethyl-3-pentanone (f) 4-Methyl-3-penten-2-one (g) Butanedial (h) 3-Phenyl-2-propenal (i) 6,6-Dimethyl-2,4-cyclohexadienone (i) p-Nitroacetophenonearrow_forwardA compound (C3H,NO) gives the following NMR data. In the box below please draw the structure of the compound. 'H-NMR: 2.06 ppm, s(3H); 7.01 ppm, t(1H); 7.30 ppm, m(2H); 7.59 ppm, d(2H); 9.90 ppm, s(1H) 13C-NMR: 168.14; 139.24; 128.511; 122.834; 118.90; 23.93 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading.arrow_forwardAn acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2-phenylpropanoic acid forms two products having different melting pointsand somewhat different solubilities. Draw the structure of these twoproducts. Assign R and S to any stereogenic centers in the products.How are the two products related? Choose from enantiomers,diastereomers, constitutional isomers, or not isomers of each other.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 Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning