Draw the product of the SN2 reaction of this amine with one equivalent of methyl iodide. Assume there is a neutralizing workup. Ignore the inorganic byproducts. NH2 CH3I (1 equiv) DMSO
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- H₂N Provide the missing structures. NH2 CH3 1) DCC N. 2) LIAIH 3) H₂O Boc₂O (1 equiv) The aliphatic amine is a stronger base/nucleophile. Why2262 Sat Aor 6 1 Which one of the following compounds is the strongest acid? CNH2 -NH2 -CO2H OH CI- СОН CH CH C A B 2. Which one of the following amines will not produce an amide when mixed with an acid chloride? NH PHCH,NH2 PHNH2 Et,NH A C 3. What is the major product of the following sequence of reactions? CH3 1) NBS, hv (excess) C(OH)3 CHO CO2H CH2O 2) NaOH, H20 (excess) A В C 4. What is the major product of the following intramolecular aldol condensation reaction? E NaOH H20 (dehydration) A C 3. D. B1. Rank the following amines A-D in order of decreasing basicity, where 1 is the most basic. NO2 A B :ZI
- 3. For the following amines, propose a stepwise synthesis for each compound. ? NH2 a) он ? b) ZI← Problem 17 of 27 Submit Draw the monoalkylation product of an amine reacting with methyl iodide. Ignore any inorganic byproducts. CHзI (1 equiv) NH2 QGive the major product for the reaction. Pyrrolidine is a secondary amine. CH CH O CH CH! O OH CH2 O CH. I CH.CH Ї TCH CHE OH CH CH₂CH₂ CH.CH CH.OH2 0= RO pyrrolidine. 2 GH CH2 3 HCI H,0 TOH OH: CH₂CH₂ TCH CH: CH₂CH. CH₂CH₂
- ethylamine NABH,CN One problem with reductive amination as a method of amine synthesis, is that by-products are sometimes obtained. For example, reductive zmination of benzaldehyde with ethylamine leads to the expected product, N-ethylbenzylamine However, significant amounts of N-methyldibenzylamine are also recovered. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism leading to the by-product. Arrow-pushing Instructions H-A OH `H NH2 :A CH3 `CH3a) What are the difficulties with the following reaction to synthesize an amine. + HBr Br + NH3 NH2 b) Show a possible alternatives to this synthesis.E. What is the saponification product of the following amide? (complete the reaction) NaOH HO, H2N а. O Na* H2N b. HO, С.
- Draw the struetre of the following three isomeic amides with chemical feruula CHNO. Amide #1: (E)-N,N-dimethyl-2-butenamide Amide #2: (7)-N-methyl-3-pentenamide Amide #3: (7)-3-hexenamide C'onsider Z sterenchemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers asing the drop-down memu in the hottom right comer. Sepamte structares with - signs from the drop-down mena. O00. IF ChemDoodle ChemDoodie ChemDoodle just the first one is what I could really use help on Amide #1: (E)-N,N-dimethyl-2-butenamide3. Ethyl phenylacetate (C,HSCH2CO,CH;CH3) is a naturally occurring ester in honey. What hydrolysis products are formed when this ester is treated with water and sulfuric acid (H2SO4)? 4. How could you prepare the following amides using an acid chloride and an amine or ammonia? (a) CH3CH2CONHCH3 (b) N,N-Diethylbenzamide (c) PropanamideWhich of the following statements about carbonyl derivatives is FALSE? O Formation of an amide from an acyl chloride requires use of two equivalents of the amine. O The product of the base-promoted saponification of an ester is a carboxylate anion. O Acetals are great protecting groups for aldehydes and ketones because they are stable to acidic conditions. O Despite being a terrible leaving group, H2N¯ is indeed the leaving group in the base-promoted hydrolysis of an amide. O Transesterification can occur under either acidic or basic reactions conditions.