4. Is this assignment giving you a headache? Propose a synthesis of ibuprofen from benzene. CO₂H Ibuprofen

Estrogens are female sex hormones, the most potent of which is B-estradiol. OH AYA Но B-Estradiol In recent years, chemists have focused on designing and synthesizing molecules that bind to estrogen receptors. One target of this research has been nonsteroidal estrogen antagonists, compounds that interact with estrogen receptors and block the effects of both endogenous and exogenous estrogens. A feature common to one type of nonste- roidal estrogen antagonist is the presence of a 1,2-diphenylethylene with one of the benzene rings bearing a dialkylaminoethoxyl substituent. The first nonsteroidal estrogen antagonist of this type to achieve clinical importance was tamoxifen, now an important drug in the treatment of breast cancer. Tamoxifen has the Z configuration shown here. NMeg A B NMeg ? ОН Tamoxifen Propose reagents for the conversion of A to tamoxifen. Note: The final step in this synthesis gives a mixture of E and Z isomers.

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POST-LABORATORY QUESTIONS 1. Effective mosquito repellents contain DEET (N,N-diethyl-3-methylbenzamide). If you were to synthesize this compound, with what carboxylic acid and amine would you start? Draw their structures. CH3 DEET O C-N CH₂CH3 CH₂CH3 H3C Metadone 2. Metadone, a narcotic analgesic (shown below as the amine), is dispensed as its hydrochloride salt. Explain the use of the salt rather than the amine. Use the structure shown and convert it to the hydrochloride salt. N-CH3 ogged