Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 21.SE, Problem 80AP
Draw the structure of the compound that produced the spectra below. The infrared spectrum has strong bands at 1720 and 1738 cm-1.
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Analysis of a sweet-smelling, neutral compound of carbon, hydrogen and oxygen produced the following results: %C = 54.5; %H = 9.1. From its mass spectrum, the molecular ion had a mass/charge ratio of 88. Its infra-red spectrum showed a prominent peak at 1735 cm–1. Figure below shows the NMR spectrum of the compound. Which of the following is this compound?
A. 3-hydroxybutanalB. Methyl propionateC. Ethyl acetateD. 2-methylpropanoic acidE. Methoxyacetone
Deduce the structure of the compound that gives the following 1H, 13C, and IR spectra.
Assign all aspects of the 1H and 13C spectra to the structure you propose. Use letters to
correlate protons with the signals in the 1H NMR spectrum, and numbers to correlate
carbons with the signals in the 13C spectrum. The mass spectrum of this compound shows
the molecular ion at m/z 148.
6H
1H
2H 2H
1H
10
8
6
4
2
84 (ppm)
CH
CH
CH3
CH
CH
200
180
160
140
120
100
80
60
40
20
100
90
80
70
60
50
40
30
20
10
4000
3000
2000
1500
1000
500
Wavenumber (cm)
Transmittance (%)
Suggest structures given the 1H NMR spectra and formulas for each of the compounds below.
C9H10O
Chapter 21 Solutions
Organic Chemistry
Ch. 21.1 - Give IUPAC names for the following substances:Ch. 21.1 - Draw structures corresponding to the following...Ch. 21.2 - Prob. 3PCh. 21.2 - Rank the compounds in each of the following sets...Ch. 21.2 - Predict the products of the following nucleophilic...Ch. 21.2 - Prob. 6PCh. 21.3 - Prob. 7PCh. 21.3 - If the following molecule is treated with acid...Ch. 21.4 - How might you prepare the following esters using a...Ch. 21.4 - Prob. 10P
Ch. 21.4 - Prob. 11PCh. 21.4 - Prob. 12PCh. 21.4 - Prob. 13PCh. 21.5 - Prob. 14PCh. 21.5 - What product would you expect from reaction of one...Ch. 21.6 - Prob. 16PCh. 21.6 - Prob. 17PCh. 21.6 - Show the products you would obtain by reduction of...Ch. 21.6 - What ester and what Grignard reagent might you...Ch. 21.7 - Prob. 20PCh. 21.7 - How would you use the reaction of an amide with...Ch. 21.8 - Write the mechanism of the reaction shown in...Ch. 21.9 - Prob. 23PCh. 21.9 - Prob. 24PCh. 21.10 - Prob. 25PCh. 21.10 - Prob. 26PCh. 21.SE - Name the following compounds:Ch. 21.SE - Prob. 28VCCh. 21.SE - Prob. 29VCCh. 21.SE - Prob. 30VCCh. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the complete...Ch. 21.SE - Prob. 35MPCh. 21.SE - When 4-dimethylaminopyridine (DMAP) is added in...Ch. 21.SE - Prob. 37MPCh. 21.SE - Prob. 38MPCh. 21.SE - Prob. 39MPCh. 21.SE - The hydrolysis of a biological thioester to the...Ch. 21.SE - Prob. 41MPCh. 21.SE - Prob. 42MPCh. 21.SE - Prob. 43MPCh. 21.SE - In the iodoform reaction, a triiodomethyl ketone...Ch. 21.SE - Give IUPAC names for the following compounds:Ch. 21.SE - Prob. 46APCh. 21.SE - Draw and name compounds that meet the following...Ch. 21.SE - Predict the product, if any, of reaction between...Ch. 21.SE - Prob. 49APCh. 21.SE - Prob. 50APCh. 21.SE - What product would you expect to obtain from...Ch. 21.SE - Prob. 52APCh. 21.SE - Prob. 53APCh. 21.SE - The following reactivity order has been found for...Ch. 21.SE - Prob. 55APCh. 21.SE - Outline methods for the preparation of...Ch. 21.SE - Prob. 57APCh. 21.SE - When ethyl benzoate is heated in methanol...Ch. 21.SE - tert-Butoxycarbonyl azide, a reagent used in...Ch. 21.SE - Prob. 60APCh. 21.SE - Prob. 61APCh. 21.SE - What is the structure of the polymer produced by...Ch. 21.SE - Polyimides with the structure shown are used as...Ch. 21.SE - Prob. 64APCh. 21.SE - Propose a structure for a compound, C4H7ClO2, that...Ch. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Prob. 67APCh. 21.SE - When a carboxylic acid is dissolved in...Ch. 21.SE - Prob. 69APCh. 21.SE - Prob. 70APCh. 21.SE - Prob. 71APCh. 21.SE - Phenyl 4-aminosalicylate is a drug used in the...Ch. 21.SE - N,N-Diethyl-m-toluamide (DEET) is the active...Ch. 21.SE - Tranexamic acid, a drug useful against blood...Ch. 21.SE - One frequently used method for preparing methyl...Ch. 21.SE - Prob. 76APCh. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Propose structures for compounds with the...Ch. 21.SE - Propose a structure for the compound with the...Ch. 21.SE - Draw the structure of the compound that produced...Ch. 21.SE - Prob. 81APCh. 21.SE - Epoxy adhesives are prepared in two steps. SN2...
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- 3 Explain the ¹H nmr spectrum of GePHs (below), and describe the structure of the molecule. 7 ¹H spectrum of GcPH,arrow_forwardReaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G?arrow_forwardThe mass spectrum of the following compound shows fragments at m/z= 127, 113, and 85. Propose structures for the ions that give rise to thesepeaks.arrow_forward
- Answer and explain in detail how you arrived at that answer.arrow_forwardTreatment of anisole (CH3OC6H5) with Cl2 and FeCl3 forms P, which has peaks in its mass spectrum at m/z = 142 (M), 144 (M + 2), 129, and 127. P has absorptions in its IR spectrum at 3096–2837 (several peaks), 1582, and 1494 cm-1. Propose possible structures for P.arrow_forwardA molecule of the molecular formula C5H11Br gives rise to the NMR spectrum below. When reacted with NaOH and water, it forms a product which by NMR has 2 protons 1H at 5.4 ppm and 1H at 5.5 ppm each having a 3J coupling of 17 Hz. (other protons also present) The product also has an IR stretch at 1550 cm 1. Provide the structures of the starting material and product. NaOH H,0 C;H„Br 6H triplet 4H quintet 1H quintet 10 8 Ppmarrow_forward
- A molecule of the molecular formula C5H11Br gives rise to the NMR spectrum below. When reacted with NaOH and water, it forms a product which by NMR has 2 protons 1H at 5.4 ppm and 1H at 5.5 ppm each having a J coupling of 17 Hz. (other protons also present) The product also has an IR stretch at 1550 cm1. Provide the structures of the starting material (1 pt) and product (2 pts) NaOH H20 C5H1,Br 6H triplet 4H quintet 1H quintet 10 8 7 6. 4 3 1 HSP-06-347 ppmarrow_forwardIndicate two basic differences that exist between the spectra of 1H y 13C in NMR.arrow_forwardcompound with formula C9H10O. If the unknown has an IR absorption at 1690 cm–1 please tell me structure ??arrow_forward
- The mass spectrum of tert-butylamine follows shows an intense base peak at m>z 58, and very little else. Use a diagram toshow the cleavage that accounts for the base peak. Suggest why no molecular ion is visible in this spectrum.1arrow_forwardTreatment of butan-2-one (CH3COCH2CH3) with strong base followed by CH3I forms a compound Q, which gives a molecular ion in its mass spectrum at 86. The IR (> 1500 cm−1 only) and 1H NMR spectrum of Q are given below. What is the structure of Q?arrow_forwardIn the presence of a small amount of acid, a solution of acetaldehyde (CH3CHO) in methanol (CH3OH) was allowed to stand and a new compound L was formed. L has a molecular ion in its mass spectrum at 90 and IR absorptions at 2992 and 2941 cm−1. L shows three signals in its 13C NMR at 19, 52, and 101 ppm. The 1H NMR spectrum of L is given below. What is the structure of L?arrow_forward
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