Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 13.SE, Problem 42AP
The acid-catalyzed dehydration of 1-methylcyclohexanol yields a mixture of two
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Chapter 13 Solutions
Organic Chemistry
Ch. 13.1 - Prob. 1PCh. 13.1 - Prob. 2PCh. 13.2 - Prob. 3PCh. 13.3 - The following 1H NMR peaks were recorded on a...Ch. 13.3 - When the 1Η NMR spectrum of acetone, CH3COCH3, is...Ch. 13.4 - Each of the following compounds has a single 1H...Ch. 13.4 - Identify the different types of protons in the...Ch. 13.5 - How many peaks would you expect in the 1H NMR...Ch. 13.6 - Predict the splitting patterns you would expect...Ch. 13.6 - Draw structures for compounds that meet the...
Ch. 13.6 - The integrated 1H NMR spectrum of a compound of...Ch. 13.7 - Identify the indicated sets of protons as...Ch. 13.7 - How many kinds of electronically nonequivalent...Ch. 13.7 - How many absorptions would you expect (S)-malate,...Ch. 13.8 - 3-Bromo-1-phenyl-1-propene shows a complex NMR...Ch. 13.9 - How could you use 1H NMR to determine the...Ch. 13.11 - Prob. 17PCh. 13.11 - Propose structures for compounds that fit the...Ch. 13.11 - Prob. 19PCh. 13.12 - Prob. 20PCh. 13.12 - Prob. 21PCh. 13.12 - Prob. 22PCh. 13.13 - Prob. 23PCh. 13.SE - Into how many peaks would you expect the 1H NMR...Ch. 13.SE - How many absorptions would you expect the...Ch. 13.SE - Sketch what you might expect the 1H and 13C NMR...Ch. 13.SE - How many electronically nonequivalent kinds of...Ch. 13.SE - Identify the indicated protons in the following...Ch. 13.SE - Prob. 29APCh. 13.SE - Prob. 30APCh. 13.SE - When measured on a spectrometer operating at 200...Ch. 13.SE - Prob. 32APCh. 13.SE - Prob. 33APCh. 13.SE - How many types of nonequivalent protons are...Ch. 13.SE - The following compounds all show a single line in...Ch. 13.SE - Prob. 36APCh. 13.SE - Propose structures for compounds with the...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - The acid-catalyzed dehydration of...Ch. 13.SE - How could you use 1H NMR to distinguish between...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Propose structures for the two compounds whose 1H...Ch. 13.SE - Prob. 46APCh. 13.SE - How many absorptions would you expect to observe...Ch. 13.SE - Prob. 48APCh. 13.SE - How could you use 1H and 13C NMR to help...Ch. 13.SE - How could you use 1H NMR, 13C NMR, and IR...Ch. 13.SE - Assign as many resonances as you can to specific...Ch. 13.SE - Assume that you have a compound with the formula...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Long-range coupling between protons more than two...Ch. 13.SE - The 1H and 13C NMR spectra of compound A, C8H9Br,...Ch. 13.SE - Propose structures for the three compounds whose...Ch. 13.SE - The mass spectrum and 13C NMR spectrum of a...Ch. 13.SE - Compound A, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - Propose a structure for compound C, which has...Ch. 13.SE - Prob. 62GPCh. 13.SE - Propose a structure for compound E, C7H12O2, which...Ch. 13.SE - Compound F, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - 3-Methyl-2-butanol has five signals in its 13C NMR...Ch. 13.SE - A 13C NMR spectrum of commercially available...Ch. 13.SE - Carboxylic acids (RCO2H) react with alcohols (ROH)...Ch. 13.SE - Prob. 68GPCh. 13.SE - The proton NMR spectrum is shown for a compound...Ch. 13.SE - The proton NMR spectrum of a compound with the...Ch. 13.SE - The proton NMR spectrum is shown for a compound...
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- By malonic or acetylacetic synthesis, synthesize 2-methylbutanoic acid (indicate the formulas of the compounds).arrow_forwardObtain 2-methylbutanoic acid by malonic or acetylacetic synthesis (indicate the formulas of the compounds involved).arrow_forwardEFFICIENTS SAMPLE READINGS CONCENTRATIONS Pigiadient) TOMATO SAUCE (REGULAR) TOMATO (REDUCED SALT) TOMATO SAUCE (REGULAR) TOMATO (REDUCED SALT) 58 6.274 3.898 301.7 151.2 14150 5.277 3.865 348.9 254.8 B 5.136 3.639 193.7 85.9 605 4.655 3.041 308.6 199.6 05 5.135 3.664 339.5 241.4 0139 4.676 3.662 160.6 87.6 90148 5.086 3.677 337.7 242.5 0092 6.348 3.775 464.7 186.4 PART3 5.081 3.908 223.5 155.8 5.558 3.861 370.5 257.1 4.922 3.66 326.6 242.9 4.752 3.641 327.5 253.3 50 5.018 3.815 336.1 256.0 84 4.959 3.605 317.9 216.6 38 4.96 3.652 203.8 108.7 $3 5.052 3.664 329.8 239.0 17 5.043 3.767 221.9 149.7 052 5.058 3.614 331.7 236.4 5.051 4.005 211.7 152.1 62 5.047 3.637 309.6 222.7 5.298 3.977 223.4 148.7 5.38 4.24 353.7 278.2 5 5.033 4.044 334.6 268.7 995 4.706 3.621 305.6 234.4 04 4.816 3.728 340.0 262.7 16 4.828 4.496 304.3 283.2 0.011 4.993 3.865 244.7 143.6 AVERAGE STDEV COUNT 95% CI Confidence Interval (mmol/L) [Na+] (mg/100 mL) 95% Na+ Confidence Interval (mg/100 mL)arrow_forward
- If we have two compounds: acetone (CH₃COCH₃) and acetic acid (CH₃COOH), applying heat to them produces an aldol condensation of the two compounds. If this is correct, draw the formula for the final product.arrow_forwardIf we have two compounds: acetone (CH3COCH3) and acetic acid (CH3COOH); if we apply heat (A), what product(s) are obtained?arrow_forwardQUESTION: Fill out the answers to the empty green boxes attached in the image. *Ensure you all incorporate all 27 values (per column)*arrow_forward
- You need to make a buffer by dissolving benzoic acid and sodium benzoate in water. What is the mass of benzoic acid that you would weigh out, in mg, to create 50 mL of a buffer at pH = 4.7 that will change pH no more than 0.10 units with the addition of 0.001 moles of acid or base? Enter just the answer without the units (mg) - just the number will do!arrow_forwardDraw the formula for 3-isopropylcyclopentane-1-carbonyl chloride.arrow_forwardQUESTION: Fill out the answers to the empty green boxes attached in the image. *Ensure you all incorporate all 27 values (per column)*arrow_forward
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