15.36 Phenylethylamine is a natural substance that is structurally similar to amphetamine. It is found in sources as diverse as almond oil and human urine, where it occurs at elevated concentrations as a result of stress and certain forms of schizophrenia. One method of synthesizing the compound for pharmacological and psychiat- ric studies involves two steps: H2 -CH2-CI + NaCN -CH2-C=N Pt -CH,-CH,-NH, phenylethylamine Classify each step as an addition, elimination, or substitution.

15.36 Phenylethylamine is a natural substance that is structurally similar to amphetamine. It is found in sources as diverse as almond oil and human urine, where it occurs at elevated concentrations as a result of stress and certain forms of schizophrenia. One method of synthesizing the compound for pharmacological and psychiat- ric studies involves two steps: H2 -CH2-CI + NaCN -CH2-C=N Pt -CH,-CH,-NH, phenylethylamine Classify each step as an addition, elimination, or substitution.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Similar questions

(b) One isomer of dimethoxybenzoic acid has 1H NMR spectrum dµ (ppm) 3.85 (6H, s), 6.63 (1H, t, J 2 Hz), and 7.17 (2H, d, J 2Hz), One isomer of coumalic acid has 'H NMR spectrum dн (ppm) 6.41 (1H, d, J 10 Hz), 7.82 (1H, dd, J 2 Hz, 10 Hz) and 8.51 (1H, d, J 2Hz). In each case, which isomer is represented here? The bonds sticking into the centre of the ring can be to any carbon atom. Note: COOH proton is not indicated in the spectra MeO HO₂C CO2H MeO dimethoxybenzoic acid coumalic acid
Hypoglycin A, an amino acid derivative found in unripened lychee, is anacutely toxic compound that produces seizures, coma, and sometimesdeath in undernourished children when ingested on an empty stomach. (a) Draw the neutral, positively charged, and negatively charged forms of hypoglycin A. (b) Which form predominates at pH = 1, 6, and 11? (c) What is the structure of hypoclycin A at its isoelectric point?
Compounds W and X are isomers. They have the molecular formula C9H8O. The IR spectrum ofeach compound shows a strong absorption band near 1715 cm−1. Oxidation of either compound withhot, basic potassium permanganate followed by acidification yields phthalic acid. The proton NMRspectrum of W shows a multiplet at δ 7.3 and a singlet at δ 3.4. The proton NMR spectrum of Xshows a multiplet at δ 7.5, a triplet at δ 3.1, and a triplet at δ 2.5. Propose structures for W and X.
PQ-4. Predict the major product(s). (A) I Br (B) II Nal acetone Q I (C) III II (D) I and II III
Which of the diethylbenzene isomers (ortho, meta, or para) corresponds to each set of 13C NMR spectral data?[A] 13C NMR signals: 16, 29, 125, 127.5, 128.4, and 144 ppm[B] 13C NMR signals: 15, 26, 126, 128, and 142 ppm[C] 13C NMR signals: 16, 29, 128, and 141 ppm
Treatment of 1,3,6-cyclononatriene (Compound 1), or its dimethyl derivative (Compound 2), with potassium amide (KNH₂) in liquid ammonia results in the formation of anion 1a or 2a, respectively (J. Am. Chem. Soc. 1973, 95, 3437-3438): 9 15.85a 2 6 3 4 5 Compound 1 (R=H) Compound 2 (R=CH3) * You answer is incorrect. KNH₂ KNH₂ 1a (anion) 2a (anion) Of the following, which is NOT one of the four resonance structures of 1a?
14. (5) Draw the structure of a compound that is consistent with the following data: a IR: 1690 cm -1 C9H1002 1Η NMR: triplet, 1.5 ppm, 3H; quartet, 4.1 ppm, 2H; doublet, 7.0 ppm, 2H; doublet, 7.7 ppm, 2H; singlet, 9.9 ppm, 1H
(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 infants
An amine of unknown structure contains one nitrogen and nine carbon atoms. The 13C-NMR spectrum shows only five signals, all between 20 and 60 ppm. Three cycles of Hofmann elimination sequence [(1) CH3I; (2) Ag2O, H3O; (3) heat] give trimethylamine and 1,4,8-nonatriene. Propose a structural formula for the amine.
15.44 Identify the following glycerophospholipid, which helps con- duct nerve impulses in the body, as a lecithin or cephalin, and list its components: O || CH,−O−C—(CH)4—CH, O || CH–0–C− (CH2)16—CH3 CH,−0-P-0–CH2–CH,-N–CH, O || Albo CH3 4+ CH3
There are several isomeric alkanes of molecular formula C6H14. Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm Isomer B: δ = 0.84 (t, 3 H), 0.86 (t, 9H), 1.22 (q, 2H) ppm
1. There are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm Isomer B: δ = 0.84 (t, 3 H), 0.86 (s, 9H), 1.22 (q, 2H) ppm