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IV. Homework Assignments Chemistry 421 HWW Fall 2012 Pick the most correct answer (show your work!): 1. Which molecule is anti aromatic? 2. Which is another name for vinylbenzene? a. phenol b. aniline c.cumene d. styrene c. anisole 3. Which is another name for CHOPh ? a. phenol b. aniline c.cumene d. styrene e . anisole 4. Which is another name for H2N-Ph? a. phenol b. aniline c.cumene d . styrene e. anisole 5. Which is another name for Ph-COOH? a. phenol b. aniline c. cumene d. benzoic acid e. anisole 6. Which reaction will likely give a rearrangement, when benzene reacts with AICI, and ? a. t-butylchloride b. 2-chloropropane c. CH,C-O(CI) d. 2-chlorobutane c. l-chloropropane 7. When benzene + l-propene + HF are mixed together, what happens? a. nothing b. n-propylbenzenec. cumene d. benzene + 2-fluoropropane e. styrene 8. When benzene+SO,/H2SO4 are mixed → a. nothing b. Ph-SO, c. Ph-SOH d. PhSO H c. none of these! 9. When benzene + Cl2 are mixed, what happens? a. nothing b. Ph-CI c. Ph-Cla on 4. Ph-Cl e. none of these! 10. When benzene + HNO3 + H2SO4 are mixed, what is produced? a. nothing b. Ph-NO, c. Ph-SO4 d. Ph-NO, e. Ph-HSO4 11. When benzene + Al (metal) and Bry mix, what forms? a. nothing b. Ph-Br c. Ph-Br2 d. Ph-Brs e, none of these! 12. What is the name of this molecule? Ph-NH2 a. anisole b. anisaldehyde c. phenylamined . aniline e . benzonitrile 13. Which path is best to make 1-butylbenzene? FeBr + benzene + ? a. l-butylbromide b. Br-C(=O)CH-CH:CH; then HCI Zn(Hg) c. 2-bromobutane d. none of these! 14. bromobenzene +(CH3),CuLi + THF / -78° followed by water quench → a. tolueneb. xylene c.cumene d. styrenee. something else!! 15. When cumene + H2SO4/ Na CrOn/water are mixed (refluxed) what is produced? a. 2-phenylpropanol b. benzoic acid c. no reaction! d. phenol c. styrene Do the following text problems: 2, 5, 7, 8, 9, 10, 15, 20, 21, 22, 23, 24, 25, 26, 27, 29, 30, 31, 32, 33, 34, 35

Answer 1

4n+2. - 4x3 + 2 It becomes aromatic It also aromatic 4n+2 - 22 4X812 It also aromatic antz It also aromatic It also aromatic 4x7+2 = 30 Another name for ringbenzen is. = styrene GHz CH=CH₂ a h Another name for CH₂o-ph is = anisole @ Another name - Benzoic for ph-cook acid Reacth of benzenet l-poopenet HF gives cumene CH₃-CH=CH₂ + HF - CH₂ - CH - Cha 4. C-CH-CH cumche

③ Reaction of benzenet so/45o gives phoso,H 50₂4 + ro He sou ② Reaction of benzene + ch gives Ph-ci 6 reaction of benzene + HNO + H₂SO4 which geres ph-No N02 HNO3 4,504 6 Reaction of benzene + Alt Br gives phaBr - Altro ③ Cumenet H.Soul Nao, giver phenol HC-CH-CH + H502/N1.56,07 → E