ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 21, Problem 21.5P
Give the IUPAC name for each
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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 21 Solutions
ORGANIC CHEMISTRY
Ch. 21 - Rank the following compounds in order of...Ch. 21 - Prob. 21.2PCh. 21 - Give the IUPAC name for each aldehyde.Ch. 21 - Prob. 21.4PCh. 21 - Give the IUPAC name for each ketone.Ch. 21 - Prob. 21.6PCh. 21 - Prob. 21.7PCh. 21 - The boiling point of is significantly higher than...Ch. 21 - Which carbonyl group in each pair absorbs at a...Ch. 21 - Problem 21.10 Draw the structure of all...
Ch. 21 - Prob. 21.11PCh. 21 - Prob. 21.12PCh. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Problem 21.15 Draw the product of each...Ch. 21 - Prob. 21.16PCh. 21 - Problem 21.17 Draw the products of the following...Ch. 21 - Problem 21.18 Outline a synthesis of each Wittig...Ch. 21 - Problem 21.19 Draw the products (including...Ch. 21 - Problem 21.20 What starting materials are needed...Ch. 21 - Prob. 21.21PCh. 21 - Problem 21.22 The product formed when reacts with...Ch. 21 - Prob. 21.23PCh. 21 - Prob. 21.24PCh. 21 - Prob. 21.25PCh. 21 - Prob. 21.26PCh. 21 - Prob. 21.27PCh. 21 - Problem 21.28 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.29 Draw the products of each...Ch. 21 - Problem 21.30 Label each compound as an acetal, a...Ch. 21 - Problem 21.31 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.32 Draw the products of each...Ch. 21 - Problem 21.33 Safrole is a naturally occurring...Ch. 21 - Prob. 21.34PCh. 21 - Problem 21.35 How would you use a protecting group...Ch. 21 - Prob. 21.36PCh. 21 - Problem 21.37 Two naturally occurring compounds...Ch. 21 - Problem 21.38 Draw the products of each...Ch. 21 - Prob. 21.39PCh. 21 - Problem 21.40 (a) Give the IUPAC name for A and B....Ch. 21 - 21.41 Rank the following compounds in order of...Ch. 21 - Prob. 21.42PCh. 21 - 21.43 Give the IUPAC name for each compound.
a....Ch. 21 - 21.44 Give the structure corresponding to each...Ch. 21 - Prob. 21.45PCh. 21 - 21.46 Draw the products of each reaction.
a. e....Ch. 21 - Prob. 21.47PCh. 21 - 21.48 Draw all stereoisomers formed in each...Ch. 21 - Prob. 21.49PCh. 21 - What products are formed when each acetal is...Ch. 21 - Prob. 21.51PCh. 21 - Prob. 21.52PCh. 21 - Which compound forms the higher concentration of...Ch. 21 - Prob. 21.54PCh. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Devise a synthesis of each alkene using a Wittig...Ch. 21 - Devise a synthesis of each compound from...Ch. 21 - Prob. 21.60PCh. 21 - Devise a synthesis of each compound from ethanol...Ch. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - 21.64 Draw a stepwise mechanism for the following...Ch. 21 - 21.65 Draw a stepwise mechanism f or the following...Ch. 21 - Prob. 21.66PCh. 21 - 21.67 Draw a stepwise mechanism for each...Ch. 21 - 21.68 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.69PCh. 21 - Prob. 21.70PCh. 21 - Prob. 21.71PCh. 21 - Prob. 21.72PCh. 21 - 21.73 Although the carbonyl absorption of cyclic...Ch. 21 - 21.74 Use the and data to determine the...Ch. 21 - 21.75 A solution of acetone in ethanol in the...Ch. 21 - Compounds A and B have molecular formula ....Ch. 21 - 21.77 An unknown compound C of molecular formula ...Ch. 21 - 21.78 An unknown compound D exhibits a strong...Ch. 21 - Prob. 21.79PCh. 21 - -D-Glucose, a hemiacetal, can be converted to a...Ch. 21 - 21.81 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.82PCh. 21 - 21.83 Draw a stepwise mechanism f or the...Ch. 21 - Prob. 21.84PCh. 21 - Prob. 21.85PCh. 21 - 21.86 Draw stepwise mechanism for the following...
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- Liquid chromatography has been used to track the concentration of remdesivir (a broad-spectrum antiviral drug, structure shown at right) in COVID patients undergoing experimental treatments. Intensity The authors provide the following details regarding standard solutions preparation: HN CN HO OH NH2 Remdesivir (RDV) stock solution (5000 µg/mL) was prepared by dissolving RDV drug powder using the mixture of DMSO: MeOH (30:70 v/v). The RDV working standard solutions for calibration and quality controls were prepared using methanol in concentrations of 100, 10, 1, 0.1, 0.01 µg/mL. 1, 2.5, 5, 7.5, 10, 25, 50, 75, 100, 250, 500, 1000, and 5000 ng/mL sample solutions were prepared freshly by spiking calibration standard solutions into the blank human plasma samples for method calibration. a) What type of calibration method is being described? Why do you think the authors chose this method as opposed to another? b) Based on the details provided in part a, describe an appropriate method blank…arrow_forwardRecent advancements in liquid chromatography include the development of ultrahigh pressure liquid chromatography (UHPLC) and an increased use of capillary columns that had previously only been used with gas chromatography. Both of these advances have made the development of portable LC systems possible. For example, Axcend Corp. makes a portable system that uses a capillary column with an internal diameter of 150-μm-that is packed with 1.7-um stationary phase particles. In contrast, a traditional LC column has a 4.6 mm internal diameter and utilizes 5-um stationary phase particles. a) Explain one advantage that is afforded by the use of a capillary column in liquid chromatographic separation. Explain one disadvantage of capillary columns. b) Explain how the use of smaller stationary phase particles can improve the resolution of a separation. Include any relevant equations that support your explanation. c) A scientist at Rowan University is using the Axcend LC to conduct analyses of F…arrow_forwardThis paper describes the use of fullerene molecules, also known as buckyballs, as a stationary phase for liquid chromatography. The performance of the fullerene-modified stationary phase (FMS) is compared to that of a more common C18 stationary phase and to two other carbon-based stationary phases, PGC and COZ. A. 10A OM B. - Figure 1. Idealized drawing of the cross-section of a pore inside a silica particle, showing the relative densities of aminopropylsilyl (red/green) and fullerene (blue) groups: (A) full cross- section; (B) detailed view of covalent bonding of fullerene to the silica surface. Surface densities of silyl and fullerene groups were inferred from elemental composition results obtained at each stage of the synthesis (see Table 1). Absorbance (mAU, 220 nm) 700 600 500 400 300 200 100 a. Define selectivity, a, with words and an equation. b. Explain how the choice of stationary phase affects selectivity. c. Calculate the resolution of the nitrobenzene and toluene peaks in…arrow_forward
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