Consider the para-substituted aromatic ketones, NO,CeH,COCH3 (p-nitroacetophenone) and CH30OC,H,COCH3 (p-methoxyacetophenone). a. Which carbonyl compound is more stable? b. Which compound forms the higher percentage of hydrate at equilibrium? c. Which compound exhibits a carbonyl absorption at higher wavenumber in its IR spectrum? Explain your reasoning in each part.
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- Show the effect of conjugation on the carbonyl absorption in an IR spectrum ?Identify products A and B from the given 1H NMR data.a. Treatment of CH2 = CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?b. Treatment of acetone [(CH3)2C = O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?Identify products A and B from the given 1H NMR data. a.Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A? b.Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?
- Answer the following questions about each of the hydroxy ketones: 1-hydroxybutan-2-one (A) and 4-hydroxybutan-2-one (B). a.) What is the molecular ion in the mass spectrum?b.) What IR absorptions are present in the functional group region?c.) How many lines are observed in the 13C NMR spectrum?d.) How many signals are observed in the 1H NMR spectrum?e.) Give the splitting observed for each type of proton as well as its approximate chemical shift.1. Why does H2 not give an IR spectrum? 2. Explain why primary amines and unsubstituted amides have two NH stretching absorptions. 3. Why do anhydrides show two carbonyl peaks? 4. HCl is known to give addition reactions to carbon-carbon double bonds. Why is this behavior not observed in this reaction? 5. Predict the structure of the product expected from addition of molecular bromine to maleic acid.Predicting the Relative Position of Carbonyl Absorptions Rank compounds A, B, and C in order of increasing frequency of the carbonyl absorption in their IR spectra.
- How many peaks would each compound show in their 13C NMR spectrum? a) eucalyptol b) linalool(b) In the IR spectrum of the product, which signals are due to the carbonyl and the alkene? NMR dibenzalacetone (expanded) 2 NMR diberzalacetone lancre this peak Ignore this peak 6 Ignore this peak PPMIdentify the carbon atoms that give rise to the signals in the 1°C NMR spectrum of each compound. a. CH;CH,CH,CH,OH; 1°C NMR: 14, 19, 35, and 62 ppm b. (CHa)2CHCHO; 1°C NMR: 16, 41, and 205 ppm c. CH2 = CHCH(OH)CH3; 1C NMR: 23, 69, 113, and 143 ppm
- 2. (9 points total) Each of the following Grignard reagents undergo reaction with CO₂ (solid). Grignard reagents: Number of ¹H NMR signals in the reaction product: CI A MgBr MeO B MgBr OMe MgBr Me MgCl a. (8 points) How many ¹H NMR signals do you expect to see in the spectrum of each product? Assume that the products are pure and that the carboxylic acid peak is present. Please write directly in the boxes. b. (1 point) Which Grignard reagent (A, B, C, or D) will lead to the product with the fewest ¹3C NMR signals?Can you detemine the substitution pattern on the aromatic ring from the following H NMR spectrum? Integrations for the signals are shown in blue. wlwwwulu 6.6 TTTE 8.6 8.4 8.2 8.0 7.8 7.6 7.4 7.2 7.0 6.8 ppm O A. Disubstituted: 1,3 O B. Trisubstituted: 1,2,4 O C. Disubstituted: 1,4 O D. Disubstituted: 1,2 O E. Monosubstituted 26 0 00 LMatch the spectra to the structures: 3-bromotoluene and methyl 4-methoxybenzoate. CH 3 3-bromotoluene 200 Spectrum B 200 Br (ignore the CDCI3 signal) CH3O methyl 4-methoxybenzoate OCH3 Spectrum A 100 100