Organic Chemistry - Access
7th Edition
ISBN: 9780321820020
Author: Bruice
Publisher: PEARSON
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Chapter 18, Problem 66P
Compound A with molecular formula C6H10 has two peaks in its 1H NMR spectrum, both of which are singlets (with ratio 9:1). Compound A reacts with an acidic aqueous solution containing mercuric sulfate to form compound B, which gives a positive iodoform test (Problem 58) and has an 1H NMR spectrum that shows two singlets (with ratio 3:1). Identify A and B.
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Compound A with molecular formula C6H10 has two peaks in its 1H NMR spectrum, both of which are singlets (with ratio 9 : 1). Compound A reacts with an acidic aqueous solution containing mercuric sulfate to form compound B, which gives a positive iodoform test and has an 1H NMR spectrum that shows two singlets (with ratio 3 : 1). Identify A and B.
Compound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 î disappears when D2O is added.
Compounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1.
1.Based on the information provided, determine the structure of compounds B and C.
2.Assign all peaks in 1H NMR spectrum of compounds B and C.
Chapter 18 Solutions
Organic Chemistry - Access
Ch. 18.1 - Prob. 1PCh. 18.1 - Prob. 2PCh. 18.1 - Prob. 3PCh. 18.1 - Prob. 4PCh. 18.1 - PROBLEM 5♦
List the compounds in each of the...Ch. 18.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 18.3 - Draw the enol tautomers for each of the following...Ch. 18.3 - Prob. 8PCh. 18.4 - Prob. 9PCh. 18.4 - Prob. 10P
Ch. 18.5 - Show how the following compounds can be prepared...Ch. 18.6 - What compound is formed when a dilute solution of...Ch. 18.7 - Prob. 13PCh. 18.7 - Prob. 14PCh. 18.7 - How many stereoisomers are obtained from each of...Ch. 18.7 - Prob. 16PCh. 18.8 - Prob. 17PCh. 18.9 - Prob. 18PCh. 18.9 - Prob. 19PCh. 18.10 - Prob. 20PCh. 18.10 - What aldehyde or ketone would be obtained when...Ch. 18.11 - Prob. 22PCh. 18.12 - Prob. 24PCh. 18.12 - What two carbonyl compound are required for the...Ch. 18.12 - Propose a mechanism for the following reaction:Ch. 18.13 - Draw the products of the following reactions:Ch. 18.13 - Prob. 28PCh. 18.13 - Prob. 29PCh. 18.14 - Prob. 30PCh. 18.15 - Write the mechanism for the reaction of a...Ch. 18.15 - Prob. 32PCh. 18.15 - Prob. 33PCh. 18.15 - Draw the product of the reaction of each of the...Ch. 18.16 - Draw the product obtained by heating each pair of...Ch. 18.16 - Prob. 36PCh. 18.17 - Prob. 37PCh. 18.18 - Prob. 38PCh. 18.18 - Prob. 39PCh. 18.19 - Prob. 40PCh. 18.20 - Prob. 42PCh. 18.21 - Propose a mechanism for the formation of...Ch. 18.21 - Prob. 44PCh. 18.21 - a. If the biosynthesis of palmitic acid were...Ch. 18.21 - Prob. 46PCh. 18 - Prob. 47PCh. 18 - Prob. 48PCh. 18 - Number the following compounds in order of...Ch. 18 - The 1H NMR chemical shifts of nitromethane,...Ch. 18 - Prob. 51PCh. 18 - Draw the products of the following reactions: a....Ch. 18 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 18 - Prob. 54PCh. 18 - Prob. 55PCh. 18 - Prob. 56PCh. 18 - Prob. 57PCh. 18 - Identify A-L. (Hint: A shows three singles in its...Ch. 18 - Using cyclopentanone as the reactant, show the...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - Prob. 61PCh. 18 - Prob. 62PCh. 18 - Prob. 63PCh. 18 - The ketone whose 1H NMR spectrum is shown here was...Ch. 18 - Prob. 65PCh. 18 - Compound A with molecular formula C6H10 has two...Ch. 18 - Indicate how each of the following compounds can...Ch. 18 - Draw the products of the following reactions:Ch. 18 - Prob. 69PCh. 18 - a. Show how the amino acid alanine can be...Ch. 18 - Prob. 71PCh. 18 - Show how the following compounds can be...Ch. 18 - Explain why the following bromoketone forms...Ch. 18 - Prob. 74PCh. 18 - What carbonyl compounds are required to prepare a...Ch. 18 - Prob. 76PCh. 18 - A carboxylic arid is formed when an -haloketone...Ch. 18 - An , -unsaturated carbonyl compound can be...Ch. 18 - Prob. 79PCh. 18 - A Cannizzaro reaction is the reaction of an...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - The following reaction is known as the benzoni...Ch. 18 - Prob. 83PCh. 18 - Prob. 84PCh. 18 - Prob. 85PCh. 18 - Prob. 86PCh. 18 - Propose a mechanism for the following reaction:
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- Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardAn unknown compound A (molecular formula C7H14O) was treated withNaBH4 in CH3OH to form compound B (molecular formula C7H16O).Compound A has a strong absorption in its IR spectrum at 1716 cm−1.Compound B has a strong absorption in its IR spectrum at 3600−3200cm−1. The 1H NMR spectra of A and B are given. What are the structuresof A and B?arrow_forwardCompound B of molecular formula C9H19N shows a noteworthy infrared absorption at 3300 cm-1. Its 1H-NMR spectrum shows three singlets – δ 1.0 (6H), 1.1 (12H), 1.4 (1H) ppm. Its 13C-NMR spectrum has four signals – δ 25, 28, 41, 64 ppm. Suggest a structure for this compound.arrow_forward
- Compound X (molecular formula C10H12O) was treated with NH2NH2, -OH to yield compound Y (molecular formula C10H14). Based on the 1H NMR spectra of X and Y given below, what are the structures of X and Y?arrow_forwardIdentify the structure of compound C (molecular formula C11H15NO2),which has an IR absorption at 1699 cm−1 and the 1H NMR spectrumshown below.arrow_forwardCompound C has the molecular formula C5H8O. The IR, 1H, 13C, and DEPT NMR spectra of this compound are shown below. (a) Calculate the double bond equivalent of compound C and briefly explain what the values obtains represents. Interpret the IR spectrum. (b) Based on the information provided, determine the structure of compound D.arrow_forward
- Compound A of molecular formula C3H6O shows a noteworthy infrared absorption at 1716 cm-1. Its 1H-NMR spectrum shows one singlet – δ 2.2 (6H) ppm. Its 13C-NMR spectrum has two signals – δ 30, 207 ppm. Suggest a structure for this compound.arrow_forwardThe IR spectrum of compound A with a molecular formula of C5H12O is shown below. Compound A is oxidized to give compound B, a ketone with a molecular formula of C5H10O. When compound A is heated with H2SO4, compounds C and D are obtained. Considerably more D is obtained than C.Reaction of compound C with O3, followed by treatment with dimethyl sulfide, gives two products: formaldehyde and compound E, with a molecular formula of C4H8O. Reaction of compound D with O3, followed by treatment with dimethyl sulfide, gives two products: compound F, with a molecular formula of C3H6O, and compound G, with a molecular formula of C2H4O. What are the structures of compounds A through G?arrow_forwardFollowing are IR and 1H-NMR spectra of compound D. The mass spectrum of compound D shows a molecular ion peak at m/z 136, a base peak at m/z 107, and other prominent peaks at m/z 118 and 59. Q.) Propose a structural formula for compound D.arrow_forward
- 1. Deduce the structure for a compound with the molecular formula, C8H8O2 and with 1H-NMR and IR spectra shown below:arrow_forwardCompound P has molecular formula C5H9C102. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forwardAn unknown compound C of molecular formula C6H12O3 exhibits a strong absorption in its IR spectrum at 1718 cm−1 and the given 1H NMR spectrum. What is the structure of C?arrow_forward
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