Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition
3rd Edition
ISBN: 9780134255644
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Textbook Question
Chapter 7.15, Problem 27P
Which of the following are aromatic?
- A CH29CHCH9CHCH9CH2
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Use the References to access important values if needed for this question.
What is the IUPAC name of each of the the following?
0
CH3CHCNH₂
CH3
CH3CHCNHCH2CH3
CH3
You have now performed a liquid-liquid extraction protocol in Experiment 4. In doing so, you
manipulated and exploited the acid-base chemistry of one or more of the compounds in your
mixture to facilitate their separation into different phases. The key to understanding how liquid-
liquid extractions work is by knowing which layer a compound is in, and in what protonation state.
The following liquid-liquid extraction is different from the one you performed in Experiment
4, but it uses the same type of logic. Your task is to show how to separate apart Compound
A and Compound B.
. Complete the following flowchart of a liquid-liquid extraction. Handwritten work is
encouraged.
•
Draw by hand (neatly) only the appropriate organic compound(s) in the boxes.
.
Specify the reagent(s)/chemicals (name is fine) and concentration as required in Boxes 4
and 5.
•
Box 7a requires the solvent (name is fine).
•
Box 7b requires one inorganic compound.
• You can neatly complete this assignment by hand and…
b) Elucidate compound D w) mt at 170 nd shows c-1 stretch at 550cm;'
The compound has the ff electronic transitions: 0%o* and no a*
1H NMR Spectrum
(CDCl3, 400 MHz)
3.5
3.0
2.5
2.0
1.5
1.0
0.5 ppm
13C{H} NMR Spectrum
(CDCl3, 100 MHz)
Solvent
80
70
60
50
40
30
20
10
0 ppm
ppm
¹H-13C me-HSQC Spectrum
ppm
(CDCl3, 400 MHz)
5
¹H-¹H COSY Spectrum
(CDCl3, 400 MHz)
0.5
10
3.5
3.0
2.5
2.0
1.5 1.0
10
15
20
20
25
30
30
-35
-1.0
1.5
-2.0
-2.5
3.0
-3.5
0.5
ppm
3.5
3.0
2.5
2.0
1.5
1.0
0.5
ppm
Chapter 7 Solutions
Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition
Ch. 7.4 - Prob. 1PCh. 7.5 - Prob. 3PCh. 7.6 - a. Predict the relative bond lengths of the three...Ch. 7.6 - Prob. 5PCh. 7.6 - Prob. 6PCh. 7.7 - Prob. 7PCh. 7.7 - Prob. 8PCh. 7.7 - Prob. 9PCh. 7.7 - Prob. 10PCh. 7.8 - Which member of each pair is the stronger acid? a....
Ch. 7.8 - Which member of each pair is the stronger base? a....Ch. 7.9 - Prob. 13PCh. 7.9 - Which species in each of the following pairs is...Ch. 7.9 - Prob. 16PCh. 7.11 - Prob. 18PCh. 7.11 - Prob. 19PCh. 7.11 - Prob. 20PCh. 7.11 - Prob. 21PCh. 7.11 - Prob. 22PCh. 7.12 - Prob. 23PCh. 7.12 - Prob. 24PCh. 7.15 - Prob. 25PCh. 7.15 - Which of the following are aromatic? A...Ch. 7.17 - Prob. 29PCh. 7.17 - Prob. 30PCh. 7 - Prob. 31PCh. 7 - Prob. 32PCh. 7 - Prob. 33PCh. 7 - Prob. 34PCh. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Which of the compounds in each of the following...Ch. 7 - Prob. 39PCh. 7 - Prob. 40PCh. 7 - Prob. 41PCh. 7 - Prob. 42PCh. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Prob. 45PCh. 7 - Which species in each of the pairs in Problem 45...Ch. 7 - Rank the following anions in order from most basic...Ch. 7 - a. Which oxygen atom has the greater electron...Ch. 7 - Prob. 49PCh. 7 - Which compound is the strongest base?Ch. 7 - Prob. 51PCh. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Prob. 55PCh. 7 - a. Which dienophile in each pair is more reactive...Ch. 7 - Prob. 57PCh. 7 - Draw the product of each of the following...Ch. 7 - Prob. 59PCh. 7 - Prob. 60PCh. 7 - Prob. 61PCh. 7 - a. In what direction is the dipole moment in...Ch. 7 - Propose a mechanism for each of the following...Ch. 7 - Prob. 1PCh. 7 - Prob. 2PCh. 7 - Prob. 3PCh. 7 - Prob. 4PCh. 7 - Prob. 5PCh. 7 - Prob. 6PCh. 7 - Prob. 7PCh. 7 - Prob. 8PCh. 7 - Prob. 9PCh. 7 - Prob. 10PCh. 7 - Prob. 11PCh. 7 - Prob. 12P
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- Part I. a) Elucidate the structure of compound A using the following information. • mass spectrum: m+ = 102, m/2=57 312=29 • IR spectrum: 1002.5 % TRANSMITTANCE Ngg 50 40 30 20 90 80 70 60 MICRONS 5 8 9 10 12 13 14 15 16 19 1740 cm M 10 0 4000 3600 3200 2800 2400 2000 1800 1600 13 • CNMR 'H -NMR Peak 8 ppm (H) Integration multiplicity a 1.5 (3H) triplet b 1.3 1.5 (3H) triplet C 2.3 1 (2H) quartet d 4.1 1 (2H) quartet & ppm (c) 10 15 28 60 177 (C=0) b) Elucidate the structure of compound B using the following information 13C/DEPT NMR 150.9 MHz IIL 1400 WAVENUMBERS (CM-1) DEPT-90 DEPT-135 85 80 75 70 65 60 55 50 45 40 35 30 25 20 ppm 1200 1000 800 600 400arrow_forward• Part II. a) Elucidate The structure of compound c w/ molecular formula C10 11202 and the following data below: • IR spectra % TRANSMITTANCE 1002.5 90 80 70 60 50 40 30 20 10 0 4000 3600 3200 2800 2400 2000 1800 1600 • Information from 'HAMR MICRONS 8 9 10 11 14 15 16 19 25 1400 WAVENUMBERS (CM-1) 1200 1000 800 600 400 peak 8 ppm Integration multiplicity a 2.1 1.5 (3H) Singlet b 3.6 1 (2H) singlet с 3.8 1.5 (3H) Singlet d 6.8 1(2H) doublet 7.1 1(2H) doublet Information from 13C-nmR Normal carbon 29ppm Dept 135 Dept -90 + NO peak NO peak 50 ppm 55 ppm + NO peak 114 ppm t 126 ppm No peak NO peak 130 ppm t + 159 ppm No peak NO peak 207 ppm по реак NO peakarrow_forwardCould you redraw these and also explain how to solve them for me pleasarrow_forward
- In the image, the light blue sphere represents a mole of hydrogen atoms, the purple or teal spheres represent a mole of a conjugate base. A light blue sphere by itself is H+. Assuming there is 2.00 L of solution, answer the following: The Ka of the left & right solution is? The pH of the left & right solution is? The acid on the left & right is what kind of acid?arrow_forwardNonearrow_forwardNonearrow_forward
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