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- ol de C 3. Caffeine is an alkaloid, meaning alkali- or base-like. Circle functional groups in the molecule which would make react as a base. CH3 CH3 a. O b. O 4. Write the equations that account for what happens in the hydrolysis of acetamide O || (CH₂C-NH₂) in (a) acid and in (b) base. woled mode) N I T CH3 H Caffeine custom page 1149. Rank the following compounds in order of increasing acidity (least acidic < most acidic) [R is an alkyl group and X is Cl, Br, or I]. a. <<< IV b. IV << | < | c. ISelect the stronger base and then draw its conjugate acid below. CICH₂CH₂O or CH3CH₂O- • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • You do not have to include lone pairs in your answer. Ⓡ OO. n[1] ? ChemDoodleWhat will the organic product of the following reaction be? Br NH₂ D). ii) base/basis5. CH:CH2ONA + CH3CH2BR 15). - + NaBr _(6a)_+ 2CUSO4. + 4NAOH » CH:COOH +(6b) + 2NA2SO4. + H2O 6.b) Rank the following alcohols from the most to the least acidic. (liic. НО. CI I но. I || Н ОН I HO CHO H3C-C-CH3 H-C-н Н CH3 " ОН ОН IV c) Indicate the oxidation state for each of the carbon atoms highlighted in red. v. НО F F H-O-OH H₂C-C-H н-с-он V ОН H3C-"-н H3C-C-CH3 ОН IV VVancomycin is an important antibiotic. It is isolated from the bacterium Streptomyces orientalis and functions by inhibiting bacterial mucopeptide synthesis. It is a last line of defense against the resistant Staph organisms that are now common in hospitals. OH HO, OH H. NHME NH H NH HO,C- “NH2 Vancomycin aglycon ОН НО In 1999, Professor Dale Boger (The Scripps Research Institute) reported a synthesis of vancomycin aglycon (aglycon = lacking a sugar) involving the following steps, among others. Compound (I) was prepared from simple starting materials by a series of steps involving forming amide bonds.Given 4-methylhexanoic acid1. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH> pKa? 2. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH = pKa? 3. How will the acid be deprotonated if the pH the solution is adjusted so that pH <pKa?9. NAHSO3 CH3 - C- CH3 19)_ 10. _(10a) NaOH → HC-O-Na + _(10b)_The blcyclic ketone shown below is first treaterd with a base, then ethyliodide is added to form the substituted ketone. Which base/conditions are sultable? 1) Base 2) O 1. Lithium diisopropylamide in THF at -78 "C. O 2. NaBH4 in methanol at room temperature. O 3. Sodium methoxide in methanol at room temperature. O 4. DBU in THF at 25 "C.4. Please write the type of reaction each equation represents (elimination, addition, rearrangement, substitution). Write your answers beneath each reaction. HNEtz Pd catatlyst NaCN acid cat он HyC CH3 Lewis acid Me -Me base UV lightLIAIH4 (excess) H30* 7. OCH3 THE NH,CH3 8. H 9. Li CH,CH,Br An enolate- A strong baseSEE MORE QUESTIONS