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Chapter 23, Problem 23.2P
Interpretation Introduction

Interpretation: A stepwise mechanism for the conversion of glyceraldehyde 3phosphate to dihydroxyacetone phosphate is to be drawn.

Concept Introduction: The chemical equilibrium that exists between a keto form of a compound and an enol form of the same compound is known as keto-enol tautomerism. Tautomers refer to these keto and enol forms. The keto-enol tautomerism takes place only if the acidic hydrogen is present at the αcarbon atom.

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2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity
Interpreting NMR spectra is a skill that often requires some amount of practice, which, in turn, necessitates access to a collection of NMR spectra. Beyond Labz Organic Synthesis and Organic Qualitative Analysis have spectral libraries containing over 700 1H NMR spectra. In this assignment, you will take advantage of this by first predicting the NMR spectra for two closely related compounds and then checking your predictions by looking up the actual spectra in the spectra library. After completing this assignment, you may wish to select other compounds for additional practice. 1. Write the IUPAC names for the following two structures: Question 2 Question 3 2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled**
11:14 ... worksheets.beyondlabz.com 3. To check your predictions, click this link for Interpreting NMR Spectra 1. You will see a list of all the - compounds in the spectra library in alphabetical order by IUPAC name. Hovering over a name in the list will show the structure on the chalkboard. The four buttons on the top of the Spectra tab in the tray are used to select the different spectroscopic techniques for the selected compound. Make sure the NMR button has been selected. 4. Scroll through the list of names to find the names for the two compounds you have been given and click on the name to display the NMR spectrum for each. In the NMR tables below, list the chemical shift, the splitting, and the number of hydrogens associated with each peak for each compound. Compare your answers to your predictions. **Not all slots must be filled** Peak Chemical Shift (d) Multiplicity 1 2 3 4 5

Chapter 23 Solutions

Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card

Ch. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.13PCh. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Problem 23.20 Which of the following compounds...Ch. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.22PCh. 23 - Prob. 23.23PCh. 23 - Prob. 23.24PCh. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - 23.31 Draw enol tautomer(s) for each compound. ...Ch. 23 - Prob. 23.32PCh. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - 23.35 Rank the labeled protons in each compound in...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - Prob. 23.40PCh. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - 23.42 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.43PCh. 23 - Prob. 23.44PCh. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - 23.46 Synthesize each compound from diethyl...Ch. 23 - Prob. 23.47PCh. 23 - Prob. 23.48PCh. 23 - Prob. 23.49PCh. 23 - 23.50 Draw the organic products formed in each...Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.52PCh. 23 - Prob. 23.53PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Prob. 23.56PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.59PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.61PCh. 23 - Prob. 23.62PCh. 23 - 23.63 Synthesize each compound from cyclohexanone...Ch. 23 - Prob. 23.64PCh. 23 - Prob. 23.65PCh. 23 - 23.66 Synthesize (Z)-hept-5-en-2-one from ethyl...Ch. 23 - Prob. 23.67PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - Prob. 23.72PCh. 23 - Prob. 23.73PCh. 23 - Prob. 23.74P
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