Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 10.9C, Problem 10.15P
Show how you would synthesize each tertiary alcohol by adding an appropriate Grignard reagent to a
- a. 3-phenylhexan-3-ol (3 ways)
- b. Ph3COH
- c. 1-ethylcyclopentanol
- d. 2-cyclopentylpentan-2-ol
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Part VII. The H-NMR of a compound with molecular formula C5 H 10 O2 is given below.
Find the following:
(a) The no. of protons corresponding to each signal in the spectra
(6) Give the structure of the compound and assign the signals to each
proton in the compound.
a
70.2
Integration Values
C5H10O2
b
47.7
C
46.5
d
69.5
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
Chemical Shift (ppm)
1.9
1.8
1.7 1.6
1.5
1.4 1.3 1.2
1.1 1.0
0.9 0.8
Part 111. 1 H-NMR spectrum of a compound with integration values in red is given below.
Answer the following:
(a) write the signals in the 'H-NMR spectrum to the corresponding protons on the structure
of the molecule below.
(b) Identify the theoretical multiplicities for each proton in the compound. Also give the possible.
complex splitting patterns assuming J values are not similar.
там
Br
22
2
3
6
4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 5.2 5.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0
Chemical Shift (ppm)
ra.
Br
2
3
6
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
Chemical Shift (ppm)
2
2
Br
7.3
7.2
7.1
7.0 6.9
6.7 6.6 6.5
6.4
6.3
6.2
6.1
6.0
Chemical Shift (ppm)
5.9
5.8 5.7
5.5 5.4 5.3 5.2
5.0 4.9
1600°
1538°C
1493°C
In the diagram, the letter L indicates
that it is a liquid. Indicate its
components in the upper region
where only L is indicated.
The
iron-iron carbide phase
diagram.
Temperature (°C)
1400
8
1394°C
y+L
1200
2.14
y, Austenite
10000
912°C
800a
0.76
0.022
600
400
(Fe)
a, Ferrite
Composition (at% C)
15
1147°C
a + Fe3C
2
3
Composition (wt% C)
L
2500
4.30
2000
y + Fe3C
727°C
1500
Cementite (Fe3C)
1000
4
5
6
6.70
Temperature (°F)
Chapter 10 Solutions
Organic Chemistry (9th Edition)
Ch. 10.3A - Prob. 10.1PCh. 10.3B - Give both the IUPAC name and the common name for...Ch. 10.3B - Prob. 10.3PCh. 10.3C - Give a systematic (IUPAC) name for each diol. a....Ch. 10.4B - Predict which member of each pair will be more...Ch. 10.4B - Dimethylamine (CH3)2NH, has a molecular weight of...Ch. 10.6A - Prob. 10.7PCh. 10.6A - Prob. 10.8PCh. 10.6C - A nitro group (NO2) effectively stabilizes a...Ch. 10.6C - Prob. 10.10P
Ch. 10.8B - Prob. 10.11PCh. 10.8B - Prob. 10.12PCh. 10.9A - Prob. 10.13PCh. 10.9B - Prob. 10.14PCh. 10.9C - Show how you would synthesize each tertiary...Ch. 10.9D - Prob. 10.16PCh. 10.9D - Show how you would add Grignard reagents to acid...Ch. 10.9D - A formate ester, such as ethyl formate, reacts...Ch. 10.9E - Prob. 10.19PCh. 10.9E - In Section9-7B, we saw how acetylide ions add to...Ch. 10.9F - Prob. 10.21PCh. 10.10A - Prob. 10.22PCh. 10.10B - Prob. 10.23PCh. 10.11B - Predict the products you would expect from the...Ch. 10.11B - Prob. 10.25PCh. 10.11B - Prob. 10.26PCh. 10.12 - Prob. 10.27PCh. 10.12 - Prob. 10.28PCh. 10.12 - Authentic skunk spray has become valuable for use...Ch. 10 - Give a systematic (IUPAC) name for each alcohol....Ch. 10 - Give systematic (IUPAC) names for the following...Ch. 10 - Draw the structures of the following compounds...Ch. 10 - Predict which member of each pair has the higher...Ch. 10 - Predict which member of each pair is more acidic,...Ch. 10 - Predict which member of each group is most soluble...Ch. 10 - Draw the organic products you would expect to...Ch. 10 - Prob. 10.37SPCh. 10 - Show how you would synthesize the following...Ch. 10 - Show how you would use Grignard syntheses to...Ch. 10 - Show how you would accomplish the following...Ch. 10 - Show how you would synthesize the following: a....Ch. 10 - Complete the following acid-base reactions. In...Ch. 10 - Prob. 10.43SPCh. 10 - Prob. 10.44SPCh. 10 - Geminal diols, or 1,1-diols, are usually unstable,...Ch. 10 - Vinyl alcohols are generally unstable, quickly...Ch. 10 - Compound A (C7H11Br) is treated with magnesium in...Ch. 10 - Prob. 10.48SPCh. 10 - Prob. 10.49SPCh. 10 - Prob. 10.50SPCh. 10 - Prob. 10.51SPCh. 10 - Prob. 10.52SPCh. 10 - Prob. 10.53SPCh. 10 - Prob. 10.54SPCh. 10 - Prob. 10.55SPCh. 10 - Prob. 10.56SPCh. 10 - Show how this 1 alcohol can be made from the...Ch. 10 - Prob. 10.58SPCh. 10 - Prob. 10.59SPCh. 10 - Prob. 10.60SP
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- Nonearrow_forwardPart II. Given below are the 'H-NMR spectrum at 300 MHz in CDC13 and mass spectrum using electron ionization of compound Brian. The FTIR of the said compound showed a strong peak at 1710 cm"). Determine the following: (a) molecular Formula and Degree of unsaturation of compound Brian (b) Basing on the given H-NMR spectrum tabulate the following (i) chemical shifts (ii) integration, ciii) multiplicity and (iv) interferences made for each signal (c) Draw the structure of compound Brian. ) ΕΙ 43 41 27 71 114 (M+) Hmmm 20 30 40 50 60 70 80 90 100 110 120 1H NMR spectrum 300 MHz in CDCl3 2.0 alle 1.0arrow_forwardThe iron-iron carbide phase diagram. In the diagram, the letter L indicates that it is a liquid. Indicate what its components are. Temperature (°C) 1600 10 Composition (at% C) 15 25 1538°C -1493°C 8 1400 1200 1394°C y+L L 2500 1147°C y. Austenite 2.14 4.30 2000 1000 912°C y + Fe3C 800ㅏ 0.76 0.022 600 a, Ferrite a + Fe3C 400 0 (Fe) Composition (wt% C) 727°C 1500 Cementite (Fe3C) 1000 6 6.70 Temperature (°F)arrow_forward
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