Homework 7 - Answers - Homework Problem Set 7 Iverson...

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Unformatted text preview: Homework Problem Set 7 Iverson CH310N Due Wednesday, March 19 NAME (Print): _____________________________ SIGNATURE: _____________________________ Chemistry 310N Dr. Brent Iverson 7th Homework March 5, 2008 Please print the first three letters of your last name in the three boxes Homework Problem Set 7 Iverson CH310N Due Wednesday, March 19 Score: _________ Homework Problem Set 7 Iverson CH310N Due Wednesday, March 19 (28 pts.) Complete the mechanism for this lactone hydrolysis is aqueous acid. Be sure to show arrows to indicate movement of all electrons, write all lone pairs, all formal charges, and all the products for each step. H O O O H H O H O H O H O H H O H H O H H O O H H O H H H O O O H H H O H H H O O O H H H O O H O H O H O H H Products O O O H H H Homework Problem Set 7 Iverson CH310N Due Wednesday, March 19 (3 or 5 pts each) Fill in the box with the product or products that are missing from the following chemical reaction equations. When a racemic mixture is formed, you must write "racemic" under both structures EVEN THOUGH YOU DREW BOTH STRUCTURES. Note: in prin cip le, this could re act on e ith er si de of the carb onyl, b ut d ue to a cce ssibi lity, i .e. th e methyl g roup is more accessible, rea ction is always o bserved at th e me th yl g roup in the se re actio ns. Haloform reaction CH3 CH3 Cu + LiCl 1) NaOH / excessBr2 2) H3 O O 1. (CH3 )2 CuLi 2. H2O OH + CHBr 3 O CH2 -P(Ph)3 SOCl2 Cl CH3 O CH2 OH H2 / Pd (1st semester) O O 1) LiAlH4 2) H2 O NH3 heat OH OH NH2 OH O Homework Problem Set 7 Iverson CH310N Due Wednesday, March 19 (3 or 5 pts each) Fill in the box with the product or products that are missing from the following chemical reaction equations. When a racemic mixture is formed, you must write "racemic" under both structures EVEN THOUGH YOU DREW BOTH STRUCTURES. PCC OH O H H2CrO 4 O Cl SOCl 2 O OH O2N OH OH CH 3 O O O NO2 1) CH3 O H2SO4 2 MgBr 2) HCl / H2O OH Homework Problem Set 7 Iverson CH310N Due Wednesday, March 19 (3 or 5 pts each) Fill in the box with the product or products that are missing from the following chemical reaction equations. When a racemic mixture is formed, you must write "racemic" under both structures EVEN THOUGH YOU DREW BOTH STRUCTURES. H3O C N heat O OH SOCl 2 O O O O Cl O 1) 2 2) H2 O O CuLi NH N O O 1) 2) HCl / H2O MgBr 1) LiAlH 4 2) H2 O OH Racemic OH N Homework Problem Set 7 Iverson CH310N Due Wednesday, March 19 10. (17 pts) Using any reagents turn the starting material into the indicated product. All carbon atoms must come from the starting material. Draw all molecules synthesized along the way. When it doubt, draw the molecule! Hint: this should look familiar as a homework problem. All the carbon atoms of the product must come from the starting material OH ? OH H2CrO 4 PBr3 Mg / ether Br Recognize the required Grignard reagent as being derived from the starting alcohol via the alkyl halide OH 1) Recognize two of the same alkyl groups attached to the tertiary alcohol, the KRE of a Grignard reacting with an ester MgBr O 2 ROH / H 2 S O4 SOCl 2 2) HCl / H2O O O R ROH O Cl Recognize this ester as the one created from the starting alcohol though an initial Jones oxidation, followed by esterification using either the Fisher esterification or initial conversion to an acid chloride followed by reaction with an alcohol. Notice that since this alcohol group does not show up in the product, for the purposes of this question, it could be any alcohol, including the starting material. Alternative An alternative route would be to convert the starting alcohol into the acid chloride via the carboxylic acid as shown, followed by reaction with the corresoponding Gilman reagent (derived from the starting alcohol via the alkyl chloride, which is treated with Li metal to give the organolithium followed by CuI to give the Gilman reagent). The resulting ketone is then reacted with the same Grignard reagent shown to give the final product. Homework Problem Set 7 Iverson CH310N Due Wednesday, March 19 (17 pts) Using any reagents turn the starting material into the indicated product. All carbon atoms must come from the starting material. Draw all molecules synthesized along the way. When it doubt, draw the molecule! Hint: this should look familiar as a homework problem. All the carbon atoms of the product must come from the starting material O N H 1) LiAlH 4 H2 / Pd 2) H2 O Recognize this amine as being derived from LiAlH4 reduction of the amide starting material. Notice the C=C is not reduced under these conditions. NH2 H 3O heat O OH Note the the reduction of the C=C bond could be done at various points, we just chose to illustrate the case when it was the first reaction. SOCl2 Recognize that the carboxylic acid required to make this acid chloride can be derived from acid hydrolysis of the starting amide. However, the C=C bond must also be removed. Therefore, there must be an H2 / Pd reduction that reduces the C=C bond, but does not reduce the carbonyl of an amide. NH2 Recognize this as an amide, the product of reaction of an acid chloride and the corresponding amine O Cl O NH2 ? O ...
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