The structure shown below is that of the E-isomer of tripolidine, an antihistamine (the E-isomer is more active than the Z-isomer in this capacity): (a) (b) H₂C- +² H 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 C=C double bond in tripolidine as illustrations. Based on the order of priority of the four groups determined in part (a) of this question, explain why the isomer of tripolidine shown above is defined as the E-isomer. (c) In general terms, explain why this isomer might have different effects in the human body from its geometric isomer.

The structure shown below is that of the E-isomer of tripolidine, an antihistamine (the E-isomer is more active than the Z-isomer in this capacity): (a) (b) H₂C- +² H 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 C=C double bond in tripolidine as illustrations. Based on the order of priority of the four groups determined in part (a) of this question, explain why the isomer of tripolidine shown above is defined as the E-isomer. (c) In general terms, explain why this isomer might have different effects in the human body from its geometric isomer.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter24: Amines And Heterocycles

Section24.SE: Something Extra

Problem 40MP

See similar textbooks

Similar questions

Answer ALL parts of this question. The structure shown below is that of one of the geometric isomers (the E- isomer) of the antidepressant, Doxepin: (a) (b) CH₂CH₂N(CH3)2 H E-Doxepin 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 C=C double bond in Doxepin as illustrations. Based on the order of priority of the four groups determined in part (a) of this question, explain why the isomer of Doxepin shown above is defined as the E-isomer. (c) In general terms, explain why this isomer might have different effects in the human body from its geometric isomer.
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).
DHA is a fatty acid derived from sh oil and an abundant fatty acid in vertebrate brains. Hydrogenation of DHA forms docosanoic acid [CH3(CH2)20CO2H] and ozonolysis forms CH3CH2CHO, CH2(CHO)2 (ve equivalents), and HCOCH2CH2CO2H. What is the structure of DHA if all double bonds have the Z conguration?
(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.
Indicate whether each statement is true or false. (a) Butanecontains carbons that are sp2 hybridized. (b) Cyclohexaneis another name for benzene. (c) The isopropyl group containsthree sp3-hybridized carbons. (d) Olefin is anothername for alkyne.
12. 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?
(a) Draw a three-dimensional line structure of (5R,6Z)-6,7-dichloro-5-hydroxynon-6-enal. Place the aldehyde group on the right-hand side of your drawing.(b) Give the Cahn-Ingold-Prelog priority order of the four groups (-OH, -H, -(CH2)3CHO, -C4H5Cl2) at the C5 stereocentre (Highest 1 > 2 > 3 > 4 Lowest).
(a) A phenyl group has the molecular formula CH- and is represented by the symbol Bn. True False (b) Para substituents occupy adjacent carbons on a benzene ring. (c) True False (e) 3-Bromobenzoic acid can be separated into cis and trans isomers. True O False (d) 1-Phenylcyclohexene is a planar molecule. True False Benzene, naphthalene, and phenanthrene are polynuclear aromatic hydrocarbons (PAHs). True
Some of the following examples can show geometric isomerism, and some cannot. Forthe ones that can, draw all the geometric isomers, and assign complete names using theE-Z system.(a) 3-bromo-2-chloropent-2-ene (b) 3-ethylhexa-2,4-diene(c) 3-bromo-2-methylhex-3-ene (d) penta-1,3-diene(e) 3-ethyl-5-methyloct-3-ene (f) 3,7-dichloroocta-2,5-diene
Draw the structures of the following molecules: (a) m-isobutylaniline (b) (S)-2-sec-butyl-2-cyclohexene-1-ol (c) (Z)-3,4-difluoro-3-hexene
(a) Why does p-dichlorobenzene have a higher m.p. than its o- and m-isomers?(b) Why is (±)-Butan-2-ol optically inactive?
11 In the six following sets, which pairs of structural for- mulas represent constitutional isomers? (a) (b) (c) (d) (e) (f) O Z-H N Η O and and and and and and i O NH₂ ОН 11. 17 18 ( (c