ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Chapter 14.12, Problem 15P
Hydrogen bonding between the oxygen of dimethyl sulfoxide (DMSO) and the proton of an
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Part V. Label ad match the carbons in compounds Jane and Diane
w/ the corresponding peak no.
in the
Spectra (Note: use the given peak no. To label the carbons, other peak
no are intentionally
omitted)
7 4 2
-0.13
-0.12
-0.11
-0.10
-0.08
8
CI
Jane
1
-0.09
5
210
200
190
180
170
160
150
140
130
120
110
100
-8
90
f1 (ppm)
11
8
172.4
172.0
f1 (ppr
HO
CI
NH
Diane
7
3
11
80
80
-80
-R
70
60
60
2
5
-8
50
40
8.
170
160
150
140
130
120
110
100
90
-0
80
70
20
f1 (ppm)
15
30
-20
20
-60
60
-0.07
-0.06
-0.05
-0.04
-0.03
-0.02
-0.01
-0.00
-0.01
10
-0.17
16
15
56
16
-0.16
-0.15
-0.14
-0.13
-0.12
-0.11
-0.10
-0.09
-0.08
-0.07
-0.06
-0.05
-0.04
17.8 17.6 17.4 17.2 17.0
f1 (ppm)
-0.03
-0.02
550
106
40
30
20
20
-0.01
-0.00
F-0.01
10
0
Chapter 14 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
Ch. 14.3 - Prob. 1PCh. 14.3 - Prob. 2PCh. 14.4 - The 1H NMR signal for bromoform (CHBr3) appears at...Ch. 14.5 - identify the most shielded and least shielded...Ch. 14.5 - (a) Assign the chemical shifts 1.6, 2.2, and 4.8...Ch. 14.5 - Assign the chemical shifts 1.1, 1.7, 2.0, and 2.3...Ch. 14.5 - Assign the chemical shifts 1.6, 4.0, 7.5, 8.2, and...Ch. 14.6 - The 300-MHz 1H NMR spectrum of 1,4-dimethylbenzene...Ch. 14.6 - Prob. 9PCh. 14.6 - How many signals would you expect to find in the...
Ch. 14.7 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.8 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.11 - Prob. 13PCh. 14.11 - Prob. 14PCh. 14.12 - Hydrogen bonding between the oxygen of dimethyl...Ch. 14.14 - Prob. 16PCh. 14.15 - The 13C NMR spectrum of 1-bromo-3-chloropropane...Ch. 14.15 - Consider carbons x, y, and z in p-methylanisole....Ch. 14.15 - Prob. 19PCh. 14.16 - To which of the compounds of Problem 14.16 does...Ch. 14.18 - DEPT spectra for a compound with the formula...Ch. 14.20 - Vibrational frequencies are sensitive to isotopic...Ch. 14.21 - Prob. 23PCh. 14.22 - Prob. 24PCh. 14.23 - Prob. 25PCh. 14.23 - Which one of the C5H8 isomers shown has its max at...Ch. 14.24 - Knowing what to look for with respect to isotopic...Ch. 14.24 - The base peak appears at m/z105 for one of the...Ch. 14.24 - Mass spectra of 1-bromo-4-propylbenzene and...Ch. 14.25 - Prob. 30PCh. 14 - Each of the following compounds is characterized...Ch. 14 - Deduce the structure of each of the following...Ch. 14 - From among the isomeric compounds of molecular...Ch. 14 - The H1NMR spectrum of fluorene has signals at 3.8...Ch. 14 - Prob. 35PCh. 14 - H1NMR spectra of four isomeric alcohols with...Ch. 14 - Prob. 37PCh. 14 - We noted in Section 14.13 that an NMR spectrum is...Ch. 14 - Identify each of the C4H10O isomers on the basis...Ch. 14 - A compound (C3H7ClO2) exhibited three peaks in its...Ch. 14 - Label nonequivalent carbons in the following...Ch. 14 - Compounds A and B are isomers of molecular formula...Ch. 14 - C13 NMR spectra for four isomeric alkyl bromides...Ch. 14 - Prob. 44PCh. 14 - Prob. 45PCh. 14 - Identify the C3H5Br isomers on the basis of the...Ch. 14 - Prob. 47PCh. 14 - A compound (C8H10O) has the IR and H1NMR spectra...Ch. 14 - Deduce the structure of a compound having the...Ch. 14 - Figure 14.53 presents IR, H1NMR, C13NMR and mass...Ch. 14 - H1NMR, C13NMR, IR, and mass spectra are shown for...Ch. 14 - 1H NMR and IR spectra for a compound with the...Ch. 14 - FriedelCraftsalkylation of benzene with...Ch. 14 - Prob. 54DSPCh. 14 - Prob. 55DSPCh. 14 - Prob. 56DSPCh. 14 - Prob. 57DSPCh. 14 - Prob. 58DSP
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- n Feb 3 A T + 4. (2 pts) Draw the structure of the major component of the Limonene isolated. Explain how you confirmed the structure. 5. (2 pts) Draw the fragment corresponding to the base peak in the Mass spectrum of Limonene. 6. (1 pts) Predict the 1H NMR spectral data of R-Limonene. Proton NMR: 5.3 pon multiplet (H Ringarrow_forwardPart VI. Ca H 10 O is the molecular formula of compound Tom and gives the in the table below. Give a possible structure for compound Tom. 13C Signals summarized C1 C2 C3 C4 C5 C6 C7 13C shift (ppm) 23.5 27.0 33.0 35.8 127 162 205 DEPT-90 + DEPT-135 + +arrow_forward2. Using the following data to calculate the value of AvapH o of water at 298K. AvapH o of water at 373K is 40.7 kJ/mol; molar heat capacity of liquid water at constant pressure is 75.2J mol-1 K-1 and molar heat capacity of water vapor at constant pressure is 33.6 J mol-1 K-1.arrow_forward
- Part VII. Below are the 'HNMR 13 3 C-NMR, COSY 2D- NMR, and HSQC 20-NMR (Similar with HETCOR but axes are reversed) spectra of an organic compound with molecular formula C6H13 O. Assign chemical shift values to the H and c atoms of the compound. Find the structure. Show complete solutions. Predicted 1H NMR Spectrum ли 4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8 f1 (ppm)arrow_forward3. Draw the expanded structural formula, the condensed structural formula, and the skeletal structural formula for 2-pentene. expanded structure: Condensed structure: Skeletal formula: 4. Draw the expanded structural formula, the condensed structural formula, and the skeletal structural formula for 2-methyl-3-heptene. expanded structure: Condensed structure: Skeletal formula: following structurearrow_forwardPart IV. Propose a plausible Structure w/ the following descriptions: a) A 5-carbon hydrocarbon w/ a single peak in its proton decoupled the DEPT-135 Spectrum shows a negative peak C-NMR spectrum where b) what cyclohexane dione isomer gives the largest no. Of 13C NMR signals? c) C5H120 (5-carbon alcohol) w/ most deshielded carbon absent in any of its DEPT Spectivaarrow_forward
- 13C NMR is good for: a) determining the molecular weight of the compound b) identifying certain functional groups. c) determining the carbon skeleton, for example methyl vs ethyl vs propyl groups d) determining how many different kinds of carbon are in the moleculearrow_forward6 D 2. (1 pt) Limonene can be isolated by performing steam distillation of orange peel. Could you have performed this experiment using hexane instead of water? Explain. 3. (2 pts) Using GCMS results, analyze and discuss the purity of the Limonene obtained from the steam distillation of orange peel.arrow_forwardPart III. Arrange the following carbons (in blue) in order of increasing chemical shift. HO B NH 2 A CIarrow_forward
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