ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
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Chapter 18.16, Problem 18.26P
Show what alcohols and carbonyl compounds give the following derivatives.
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Students have asked these similar questions
On the next page is an LC separation of the parabens found in baby wash. Parabens are
suspected in a link to breast cancer therefore an accurate way to quantitate them is desired.
a. In the chromatogram, estimate k' for ethyl paraben. Clearly indicate what values you used for
all the terms in your calculation.
b. Is this a "good" value for a capacity factor? Explain.
c. What is the resolution between n-Propyl paraben and n-Butyl paraben? Again, indicate clearly
what values you used in your calculation.
MAU
| Methyl paraben
40
20
0
-2
Ethyl paraben n-Propyl paraben
n-Butyl paraben
App ID 22925
6
8
min
d. In Figure 4, each stationary phase shows some negative correlation between plate count
and retention factor. In other words, as k' increases, N decreases. Explain this relationship
between k' and N.
Plate Count (N)
4000
3500
2500
2000
1500
1000
Figure 4. Column efficiency (N) vs retention factor (k') for 22
nonionizable solutes on FMS (red), PGC (black), and COZ (green). 3000
Eluent compositions (acetonitrile/water, A/W) were adjusted to obtain
k' less than 15, which was achieved for most solutes as follows: FMS
(30/70 A/W), PGC (60/40), COZ (80/20). Slightly different
compositions were used for the most highly retained solutes. All
columns were 50 mm × 4.6 mm id and packed with 5 um particles,
except for COZ, which was packed with 3 um particles. All other
chromatographic conditions were constant: column length 5 cm,
column j.§. 4.6 mm, flow rate 2 mL/min, column temperature 40 °C,
and injection volume 0.5 μL
Log(k'x/K'ethylbenzene)
FMS
1.5
1.0
0.5
0.0
ཐྭ ཋ ཤྩ བྷྲ ;
500
0
5
10…
f. Predict how the van Deemter curve in Figure 7
would change if the temperature were raised
from 40 °C to 55 °C.
Figure 7. van Desmter curves in reduced coordinates for four
nitroalkane homologues (nitropropane, black; nitrobutane, red;
nitropentane, blue; and nitrohexane, green) separated on the FMS
phase. Chromatographic conditions: column dimensions 50 mm × 4.6
mm id, eluent 30/70 ACN/water, flow rates 0.2-5.0 mL/min, injection
volume 0.5 and column temperature 40 °C. No corrections to the
plate heights have been made to account for extracolumn dispersion.
Reduced Plate Height (h)
°
20
40
60
Reduced Velocity (v)
8. (2) A water sample is analyzed for traces of benzene using headspace analysis. The sample and
standard are spiked with a fixed amount of toluene as an internal standard. The following data are
obtained:
Ppb benzene
Peak area benzene
Peak area toluene
10.0
252
376
Sample
533
368
What is the concentration of benzene in the sample?
Chapter 18 Solutions
ORGANIC CHEMISTRY
Ch. 18.3 - Give the IUPAC name and (if possible) a common...Ch. 18.5D - NMR spectra for two compounds are given here,...Ch. 18.5D - Why were no products from the McLafferty...Ch. 18.5D - Use equations to show the fragmentation leading to...Ch. 18.5E - Prob. 18.5PCh. 18.7D - Show how you would synthesize each compound from...Ch. 18.8 - Prob. 18.7PCh. 18.9 - Predict the products of the following reactions....Ch. 18.9 - Show how the following transformations may be...Ch. 18.10 - Prob. 18.10P
Ch. 18.11 - Show how you would accomplish the following...Ch. 18.11 - Prob. 18.12PCh. 18.12 - Propose mechanisms for a. the acid-catalyzed...Ch. 18.12 - Rank the following compounds in order of...Ch. 18.13 - Prob. 18.15PCh. 18.13 - Show how you would accomplish the following...Ch. 18.14 - Prob. 18.17PCh. 18.14 - Prob. 18.18PCh. 18.14 - Prob. 18.19PCh. 18.14 - Prob. 18.20PCh. 18.15 - 2,4-Dinitrophenylhydrazine is frequently used for...Ch. 18.15 - Prob. 18.22PCh. 18.15 - Prob. 18.23PCh. 18.16 - Prob. 18.24PCh. 18.16 - Prob. 18.25PCh. 18.16 - Show what alcohols and carbonyl compounds give the...Ch. 18.16 - In the mechanism for acetal hydrolysis shown, the...Ch. 18.16 - Prob. 18.28PCh. 18.17 - Show how you would accomplish the following...Ch. 18.18 - Prob. 18.30PCh. 18.18 - Prob. 18.31PCh. 18.18 - Prob. 18.32PCh. 18.18 - Show how Wittig reactions might be used to...Ch. 18.19 - Predict the major products of the following...Ch. 18.20C - Prob. 18.35PCh. 18.20C - Predict the major products of the following...Ch. 18 - Draw structures of the following derivatives. a....Ch. 18 - Prob. 18.38SPCh. 18 - Predict the major products of the following...Ch. 18 - Rank the following carbonyl compounds in order of...Ch. 18 - Acetals can serve as protecting groups for...Ch. 18 - Sketch the expected proton NMR spectrum of...Ch. 18 - A compound of formula C6H10O2 shows only two...Ch. 18 - The proton NMR spectrum of a compound of formula...Ch. 18 - The following compounds undergo McLafferty...Ch. 18 - An unknown compound gives a molecular ion of m/z...Ch. 18 - Show how you would accomplish the following...Ch. 18 - Prob. 18.48SPCh. 18 - Prob. 18.49SPCh. 18 - Propose mechanisms for the following reactions.Ch. 18 - Show how you would accomplish the following...Ch. 18 - Show how you would synthesize the following...Ch. 18 - Predict the products formed when cyclohexanone...Ch. 18 - Predict the products formed when...Ch. 18 - Show how you would synthesize octan-2-one from...Ch. 18 - Prob. 18.56SPCh. 18 - Both NaBH4 and NaBD4 are commercially available,...Ch. 18 - When LiAIH4 reduces 3-methylcyclopentanone, the...Ch. 18 - Prob. 18.59SPCh. 18 - Show how you would accomplish the following...Ch. 18 - There are three dioxane isomers 1,2-dioxane,...Ch. 18 - Two structures for the sugar glucose are shown on...Ch. 18 - Prob. 18.63SPCh. 18 - Prob. 18.64SPCh. 18 - Prob. 18.65SPCh. 18 - Prob. 18.66SPCh. 18 - Within each set of structures, indicate which will...Ch. 18 - Prob. 18.68SPCh. 18 - Prob. 18.69SPCh. 18 - Prob. 18.70SPCh. 18 - The UV spectrum of an unknown compound shows...Ch. 18 - a. Simple aminoacetals hydrolyze quickly and...Ch. 18 - The mass spectrum of unknown compound A shows a...Ch. 18 - Prob. 18.74SPCh. 18 - Prob. 18.75SPCh. 18 - Prob. 18.76SPCh. 18 - Prob. 18.77SP
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