9:55 PM 76 B/s Edit CHEM 202 ASSIGNMENT # 1 – DUE ON WEDNESDAY, 8TH APRIL 2020 1. Give the IUPAC name or draw the structure, whichever is required for each of the following: осHз COOH OH (a) (b) (c) -CH3 NH2 CI (d) 4-hydroxybenzaldehyde Bromobenzyl chloride (h) 2,4-dimethylaniline 2. Use the following list of compounds to answer the questions below: [4 pts. each] (e) p-methoxytoluene (f) p-Nitroanisole (bg) m- D Н НС AB AC AD AE BC Select the compound that is best described as: (a) A neutral antiaromatic aromatic system electron system (d) A non-aromatic, conjugated, 6 pi (b) An aromatic system with n= 2 in the 4n+2 Huckel rule (e) A 6 pi electron aromatic system (c) A neutral, 4 p-electron, anti-aromatic system 3. Identify the molecule/species which are aromatic and those which are anti-aromatic: 4. What is the formula of the electrophilic reagent/species present in the following reaction? 88 Tools Mobile View Share 9:56 PM Edit Br, ? FeBr3 A single organic product was isolated after Birch reduction of p-xylene. Suggest a reasonable structure for this substance. 5. 6. Chromic oxidation of 4-t-butyl-1,2-dimethylbenzene yielded a single compound having the molecular formula C12H1404. What was this compound? 7. Nitration of 1,4-dimethylbenzene (p-xylene) gives a single product with mol. formula CsH9NO2 in high yield. What is the product? 8. What product would you expect from the bromination of p-methylbenzoic acid? 9. From the following list, identify the groups which are activating and ortho, para directors and those which are deactivating, meta directors when attached to a benzene ring: -ci ; -N(CH3)2 ; -NO2 ; -ОСНз ; -NHCOCH3. 10. Give the structure of the principal organic product formed on reaction of benzyl bromide with each of the following reagents: (a) sodium ethoxide (b) potassium t-butoxide (c) sodium azide (d) sodium hydrogen sulfide (e) sodium iodide (in acetone) 11. Order the following compounds according to their activating substituents (from least activating to most activating: NO2 NH. осн, ÇOOH (1) (11) (iv) (v) 12. Rank the following in terms of increasing reactivity toward nitration with HNO3, H2SO4 (least to most): NHCH, 13. Rank the following in each group in order of their reactivity toward electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, aniline 14. Give the major product(s) for each of the following reactions. Indicate whether the reaction proceeds faster or slower than the corresponding reaction of benzene. NO2 HNO3 so, (a) (b) H2S0 4 H2SO 4 В г, (c) FeB r3 15. Write the formula of the electrophilic reagent/species present in each reaction of the preceding problem (#9). 16. Provide the reactant, reagent, or product omitted from each of the following: 88 DO Tools Mobile View Share