Table 1 shows the results of the five experiments in the study. Experiment Organ
ID: 500592 • Letter: T
Question
Table 1 shows the results of the five experiments in the study.
Experiment Organic substrate
(Compound 1) Major Product/ Minor Product
1 Styrene
(R = H) Compound 2 Yes
2 4-Methylstyrene
(R = -CH3) Compound 2 No
3 4-Nitrostyrene
(R = -NO2) Compound 3 No
4 4-Trifluoromethylstyrene
(R = -CF3) Compound 3 No
5 4-Chlorostyrene
(R = Cl) Compound 2 and 3 Yes
Note: Yes in the last column of Table 1 means that minor products do form during the experiment, and No means that minor products do not form.
1A) In Experiment 1, the major product results from what type of reaction?
(a) An addition reaction.
(b) A substitution reaction.
(c) An elimination reaction.
(d) A cleavage reaction.
1B) The minor products of Experiment 1 result from mononitration of the aromatic ring.
These by-products are related structurally in that they are
(a) diastereomers
(b) resonance forms
(c) constitutional isomers
(d) enantiomers
1C) Is the hypothetical explanation that Compound 3 (R = -NO2) arises from an SN2 reaction between Compound 2 and HNO3 a plausible explanation?
(a) Yes, because the nitro group bonds to a primary carbon atom, which favors an SN2 reaction
(b) Yes, because the –ONO2 group activates the site of substitution
(c) No, because SN2 reactions do not occur on aromatic substrates
(d) No, because hydride ion cannot serve as a leaving group
1D) Which of the following structures shows the major product of a reaction between 4-ethylstyrene and anhydrous acid and nitric acid in dichloromethane?
1E) A reaction between Compound 1, where R is an acetyl group (-COCH3), and nitric acid would most closely mimic which experiment shown in Table 1?
(a) Experiment 1
(b) Experiment 2
(c) Experiment 3
(d) Experiment 5
4. A chemist conducted a series of experiments in which styrene and para-substituted styrenes were allowed to react with anhydrous nitric acid in dichloromethane. Figure 1 shows the structures of some of the reactants the chemist used and the products obtained in the study. ONO, ONO, CH NO Compound 1 Compound 2 Compound 3 Figure 1 Table 1 shows the results of the five experiments in the study. Table 1 Major Product Minor Organic substrate Experiment Product (Compound l) Compound 2 Yes Styrene (RSH) Compound 2 No 4-Methylstyrene (R -CH3) Compound 3 No 4-Nitrostyrene (R NO2) 4- Trifluoromethylstyrene Compound 3 No (R -CF3) Compound 2 Yes 4-Chlorostyrene and 3 (R-C) Yes in the last column of means that minor products do form during the experiment, and No means that minor products do not form.Explanation / Answer
1A) In Experiment 1, the major product results from (a) An addition reaction.
1B) The minor products of Experiment 1 result from mononitration of the aromatic ring.
These by-products are related structurally in that they are (c) constitutional isomers.
1C) Is the hypothetical explanation that Compound 3 (R = -NO2) arises from an SN2 reaction between Compound 2 and HNO3 a plausible explanation?
(d) No, because hydride ion cannot serve as a leaving group
1D) The structure of (b) shows the major product of a reaction between 4-ethylstyrene and anhydrous acid and nitric acid in dichloromethane?
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