4. There are two aromatic rings from the molecules shown below. Which ring in each undergoes electrophilic aromatic substitution more readily? Draw the major product formed on nitration 4a; 4b; and 4c. (b) O,N- (c) ČNH
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- Rank the compounds in each group in order of increasing reactivity in electrophilic aromatic substitution: (a) C6H6, C6H5Cl, C6H5CHO, C6H5OCH3; (b) C6H5CH3, C6H5NH2, C6H5CH2NH2, C6H5CONH2.Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict themajor products of the reactions of naphthalene with the following reagents.(a) HNO3, H2SO4 (b) Br2, FeBr3 (c) CH3CH2COCl, AlCl3(d) isobutylene and HFElectrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict themajor products of the reactions of naphthalene with the following reagents.(a) HNO3, H2SO4 (b) Br2, FeBr3 (c) CH3CH2COCl, AlCl3
- Chemistry 3. Complete the following reaction scheme. Give all product(s) and indicate major or minor and any relevant stereochemistry. (а) NaOEt heat (b) heat (c) Br NaCN DMF (d) (e) OH H,SO,/H,PO, heat (f) HBr (g) 1) BH. THE 2) H,0, OH (h) 1) Hg(OAC), H-0 2) NaBH, (i) KMNO, NaOH ColdElectrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict themajor products of the reactions of naphthalene with the following reagents.(a) HNO3, H2SO42) Identify whether each of the following reaction performs a SN1, SN2, E1 or E2; Then, draw the appropriate products. Meo (a) NH2 (d) Br Br он (b) (e) ELOH HO Br (c) (f) Br
- Determine whether each of the following syntheses requires a reaction that alters the carbon skeleton. (a) (b) OH (c) (d) OCH,CH3 CH3 (e) OH (f) H,CO он H;CO. (g) H3CO, (h) H3CO. NO2 NO2Consider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major produces) formed when this compound is treated with one equivalent of Br2?Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.
- 1. At what position and on what ring would you expect the following substances to undergo electrophilic substitution? (b) CH3 Br lel CH3 2. Rank the compounds in each group according to their reactivity toward electrophilic substitution. (a) Chlorobenzene, o-dichlorobenzene, benzene (b) p-Bromonitrobenzene, nitrobenzene, phenol (c) Fluorobenzene, benzaldehyde, 0-xylene (d) Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrile7В. (2 Draw the structure of the product, substrate or condition in the following reactions (should clearly indicate the stereochemistry). (а) OH (b) OsO vaHSO3 (c) 1) (sia)2 BH 2) NaOH/H,O2 H20 (d) HBr (2 equiv) Br, Br Hint: This is the only product formed (e) Br Br2 H20 OH (f)c) Write a detailed mechanism for the following transformation: OH CH;OH H,SO, (cat)