(a)
Interpretation:
The preparation of the 1-bromo-3-nitrobenzene from benzene or toluene or phenol has to be shown.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of
Activating groups – ortho/para directing groups. The
Deactivating groups – metadirecting groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
(a)
Explanation of Solution
Given target compound,
Step 1: Nitration of benzene ring by the reaction of benzene with nitrating mixture.
Step 2: Halogenation of nitrobenzene by the reaction of nitrobenzene with bromine in the presence of Lewis acid.
(b)
Interpretation:
The preparation of the 1-bromo-4-nitrobenzene from benzene or toluene or phenol has to be shown.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.
Activating groups – ortho/para directing groups. The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.
Deactivating groups – metadirecting groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
(b)
Explanation of Solution
Given target compound,
Step 1: Halogenation of benzene by the reaction of benzene with bromine in the presence of Lewis acid.
Step 2: Nitration of bromobenzene by the reaction of bromobenzene with nitrating mixture.
(c)
Interpretation:
The preparation of the 2,4-6-trinitrotoluene from benzene or toluene or phenol has to be shown.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.
Activating groups – ortho/para directing groups. The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.
Deactivating groups – metadirecting groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
(c)
Explanation of Solution
Given target compound,
Methyl group in toluene is an activating and ortho-para directing group, so three times nitration of toluene gives the target compound.
(d)
Interpretation:
The preparation of the m-chlorobenzoic acid from benzene or toluene or phenol has to be shown.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.
Activating groups – ortho/para directing groups. The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.
Deactivating groups – metadirecting groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
(d)
Explanation of Solution
Given target compound,
Step 1: Oxidation of toluene with chromic acid gives the benzoic acid.
Step 2: Carboxyl group is a deactivating and meta directing group so the chlorination takes place at the meta position.
(e)
Interpretation:
The preparation of the p-chlorobenzoic acid from benzene or toluene or phenol has to be shown.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.
Activating groups – ortho/para directing groups. The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.
Deactivating groups – metadirecting groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
(e)
Explanation of Solution
Given target compound,
Step 1: Halogenation of toluene by the reaction of toluene with chlorine in the presence of Lewis acid.
Step 2: Oxidation of 4-chlorotoluene by chromic acid gives the target compound.
(f)
Interpretation:
The preparation of the p-dichlorobenzene from benzene or toluene or phenol has to be shown.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.
Activating groups – ortho/para directing groups. The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.
Deactivating groups – metadirecting groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
(f)
Explanation of Solution
Given target compound,
Step 1: Halogenation of benzene by the reaction of benzene with chlorine in the presence of Lewis acid.
Step 2: Second halogenation of chlorobenzene by the reaction of chlorobenzene with chlorine in the presence of Lewis acid.
(g)
Interpretation:
The preparation of the 1-bromo-4-nitrobenzene from benzene or toluene or phenol has to be shown.
Concept Introduction:
Activating and deactivating groups:
The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.
Activating groups – ortho/para directing groups. The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.
Deactivating groups – metadirecting groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.
(g)
Explanation of Solution
Given target compound,
Step 1: Nitration of benzene by the reaction of benzene with nitrating mixture.
Step 2: Sulfonation of nitrobenzene by the reaction with
Want to see more full solutions like this?
Chapter 22 Solutions
Organic Chemistry
- 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
- Normalized Intensity (a. u.) 0.5 1.0 A 3D-printed GC column (shown below) was created for use with "micro" gas chromatography applications. To prove its utility, it was used to separate a mixture of alkanes (C9-C18, C22, C24). For the separation shown below, the column temperature was ramped from 40 °C to 250 °C at a rate of 30 °C per minute. (a) 9 10 = 1 mm 12 13 15 22 0.0 0 100 200 300 400 Time (sec) a) What detector would you use for this analysis? Justify your selection. b) Explain how the chromatogram would change if the separation was run isothermally. c) Explain how the chromatogram would change if the temperature ramp were increased to 50 °C per minute.arrow_forwardDevise a synthesis of each compound from the indicated starting material. You may also use any organic compounds with one or two carbons and any needed inorganic reagents. a. Brarrow_forwardPlease help me with #2b & #3 using the data.arrow_forward
- Heparin is used as an anti-coagulant. A risk of heparin use is thrombocytopenia, or low platelet count. This risk is minimized with the use of low molecular weight heparins (LMWH), therefore it is desirable to separate LMWH from higher molecular weight heparins. The method of choice to do this is molecular exclusion chromatography. Below is a chromatogram from a molecular exclusion chromatographic run. Peaks ranging from A to J are clearly distinguishable. The heparin mixture that was analyzed had anywhere from 6 to 30 repeat units of monomer (where the heparin with 30 repeat units would be roughly five times the size of the heparin with six repeat units). a. Which letter most likely represents the peak with 6 repeat units given these heparin polymers were separated with molecular exclusion chromatography? b. Explain your reasoning describing the mechanism of retention in molecular exclusion chromatography. 100 80 60 60 Relative Abundance 40 40 E GH 20 20 B A 36 38 40 42 44 46 48 50 50…arrow_forwardHELP NOW PLEASE ! URGENT!arrow_forwardHELP NOW PLEASE ! URGENT!arrow_forward
Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,
General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning