HINT: Integration is just a ratio not the actual number of hydrogens. Q1: The following alcohol undergoes elimination in the presence of concentrated sulfuric acid, but the product shown is not its chief product. Instead, another isomeric six-carbon alkene forms. This product shows a large peak at 20.4 ppm and a smaller one at 123.4 ppm in its proton-decoupled 13C NMR spectrum. Draw the structure of the product and interpret the spectrum. Outline a mechanism for the formation of the product that possesses this spectrum. CH3 CH;-CH-CH-CH2-OH CH3 CH;-CH-C=CH2 + H,0 CH, H,SO, %3D

HINT: Integration is just a ratio not the actual number of hydrogens. Q1: The following alcohol undergoes elimination in the presence of concentrated sulfuric acid, but the product shown is not its chief product. Instead, another isomeric six-carbon alkene forms. This product shows a large peak at 20.4 ppm and a smaller one at 123.4 ppm in its proton-decoupled 13C NMR spectrum. Draw the structure of the product and interpret the spectrum. Outline a mechanism for the formation of the product that possesses this spectrum. CH3 CH;-CH-CH-CH2-OH CH3 CH;-CH-C=CH2 + H,0 CH, H,SO, %3D

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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10)Pyrrolium (1) and pyridinium (2) have markedly H different pK, values. Circle the compound with the lower pK₂ value. -N-H 11) The 1H NMR spectrum of phenol is shown below. Of note, the aryl proton signals resolve in this molecule. Assign protons to specific signals in the spectrum 8 7 6 H₂ H₁ 5 ppm H3 H₂ *CHCl3 2 H₁
3. A student performed the following reaction and obtained a product with a chemical formula of C6H120. Use the chemical formula and 'H NMR spectrum to determine the structure of the product. (No peaks exchange with D20). Then propose a mechanism for the reaction. H* / H20 OH но singlet 1= 6 triplet |= 2 quintet | = 2 triplet |= 2 4.0 3.0 2.0 1.0 0.0 8 (ppm) Mechanism:
looking at this reaction (first image), The second image shows the 13C NMR spectrum of the 2-acetnaphthone which is the starting material and an 13C NMR spectrum obtained for the reaction product: Based a comparison of the two 13C NMR spectra, is product A or product B the major product of the reaction? - Explain your reasoning.
Recognize which of the five listed molecules produces the 'H NMR spectrum shown. (1) HẠC-CH2-CH2-CH2-CHO (2) H3C-CH2-CH2- (3) H,C-CH-CH-CH, CH3 O (4) H3C-CH- CH3 (5) HỌC−C−CHO CH3 -CH3 11 10 Molecule (1) Molecule (2) Molecule (3) Molecule (4) Molecule (5) 6 8 7 6 5 4 3 2 1 ppm
Saturated aldehyde Aromatic aldehyde At what position would you expect to observe IR absorption for the carbonyl groups in the following molecules? Infrared Absorptions of Some Aldehydes and Ketones. Carbonyl type Absorption cm-1 1730 1705 Example CH3CHO PhCHO a,ẞ-Unsaturated H2C=CHCHO 1705 aldehyde Saturated ketone CH3 COCH3 1715 Cyclohexanone 1715 Cyclopentanone 1750 Cyclobutanone Aromatic ketone 1785 PhCOCH3 a,ẞ-Unsaturated ketone H2C=CHCOCH3 1685 1690 Molecule #1: Molecule #2: CHO CHO CH3 cm-1 cm -1
Steps in Spectral Identification: •Identify major peaks in IR spectrum, if any. •Deduce structural fragments for each of the 1H NMR spectral signals. •Give the structure of the compound •Assign the signals in the 1H NMR spectra to specific protons •Assign carbons to the peaks in the 13C NMR spectrum Step 1. Calculate the degree of unsaturation for the unknown. Step 2. Determine the functional group from IR Step 3. Analyzing the MS spectrum Step 4. Analyzing the 1H NMR spectra Determine the number of different kinds of protons Step 5. Analyzing the 13C NMR spectra
Please identify Molecule A, formed from the reaction shown, from the 13C NMR spectra shown. All peaks below are single peaks (no overlapping peaks). Inset is an expansion of the downfield section of the spectra.
1. How many proton signals would you expect to see in the ¹H-NMR spectrum of the following molecule? For each of the proton signals, predict the splitting pattern, assuming that you can see only 3-bond splitting.
What would be the major product of this reaction? Discuss the 1H-NMR spectrum of the product and significant changes between the starting material and your product.
Which of these choices best describes the interpretation of the following peak that may be recorded in a 'H NMR spectrum? 2.5 8 (2H, d). The underlined hydrogen atom is intended to be the one producing the peak that we are interpreting. O=C-CH,CO2H O=C-CH2CHX2 O=C-CH2CH2X O=C-CH2CH3 None of these interpretations describes this peak.
Steps in Spectral Identification: •Identify major peaks in IR spectrum, if any. •Deduce structural fragments for each of the 1H NMR spectral signals. •Give the structure of the compound •Assign the signals in the 1H NMR spectra to specific protons •Assign carbons to the peaks in the 13C NMR spectrum Step 1. Calculate the degree of unsaturation for the unknown. Step 2. Determine the functional group from IR Step 3. Analyzing the MS spectrum Step 4. Analyzing the 1H NMR spectra Determine the number of different kinds of protons Step 5. Analyzing the 13C NMR spectra