Homework 8 - Answers

Homework 8 - Answers - Homework Problem Set 8 Iverson...

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Unformatted text preview: Homework Problem Set 8 Iverson CH310N Due Wednesday, April 9 NAME (Print): _____________________________ SIGNATURE: _____________________________ Chemistry 310N Dr. Brent Iverson 8th Homework April 2, 2008 Please print the first three letters of your last name in the three boxes Homework Problem Set 8 Iverson CH310N Due Wednesday, April 9 Score: _________ Homework Problem Set 8 Iverson CH310N Due Wednesday, April 9 (20 Points) Fill in the missing arrows and reagents to complete this roadmap using all the reactions you have learned this semester that interconvert these types of molecules. Homework Problem Set 8 Iverson CH310N Due Wednesday, April 9 (3 or 5 pts each) Fill in the boxes with the appropriate structure or structures. Because these structures are getting complex, you do not need to draw both enantiomers. Instead, when a new chiral center is created, just mark it with an asterisk (*) and label the product as "racemic". No need to use wedges and dashes. Also, when an E,Z mixture is formed, only draw one and label it as "E,Z mixture". Finally, the "" sign means that heat is used in the reaction. These directions apply to all of the following pages as well. O E,Z Mixture H E,Z Mixture O H O H 1) 0.5 eq. LDA 2) H3O 1.0 eq. LDA O /! 1) catalytic NaOH 2) H3O /! H N H /H 1) 1.0 eq. NaOH 2) H3O 1) 1.0 eq. LDA O 2) H /! O E,Z Mixture H H N + H2 O (some Z product might be formed, but only a small amount) 3) H3O O E,Z Mixture /! H Crossed aldol Homework Problem Set 8 Iverson CH310N Due Wednesday, April 9 O O O O HO Racemic O * O O 1.0 eq. NaOH 1.0 eq. LDA 1) 0.5 eq. NaOEt 2) H3O O O (Mild acid) 0.5 eq. LDA 1) 0.5 eq. LDA O O O 2) H3O (Mild acid) 1) 1.0 eq. NaOEt 2) H3O (Mild acid) O * O O Racemic O * O O Racemic Homework Problem Set 8 Iverson CH310N No dehydration here because no acid/heat treatment OH * Racemic * H O Due Wednesday, April 9 O E,Z Mixture H Wolff-Kishner catalytic NaOH (No acid or heat) H2NNH2 / NaOH O 1) catalytic NaOH 2) H3O /! H OH / H 1) 1.0 eq. LDA O 1) 1.0 eq. NaOH 2) H3O /! HO 2) O O H Acetal formation O H 3) H3O /! H O H E,Z Mixture E,Z Mixture Crossed aldol Homework Problem Set 8 O Iverson CH310N Due Wednesday, April 9 O 0.5 eq. NaOEt O Mild H3O No heat O O O O O Br Racemic * O 1) Strong H3O 2) Heat (!) O + CO2 HO O O 1) 2) H3O MgBr * OH Racemic Homework Problem Set 8 Iverson CH310N Due Wednesday, April 9 O H H O O 1) catalytic NaOH 2) H3O /! H O O O O O O 1) 1.0 eq. NaOEt 2) mild H3O * O O Dieckmann Racemic 1) 1.0 eq. NaOEt 2) O O 3) H3O /! O Robinson * O Racemic 1) 1.0 eq. NaOEt Malonic ester synthesis O O O HO 2) O 3) Strong H3O Br O /! + CO2 + 2 HOEt O 1) O3 2) (CH3)2S H O O H 1) catalytic NaOH 2) H3O /! H Homework Problem Set 8 Iverson CH310N Due Wednesday, April 9 O 1) 1 Eq. NaOEt O O 2) O 3) Mild H3O O 1) 1 Eq. NaOEt O O 2) NH2 O O O * O Racemic O O 3) Mild H3O O 1) 1 Eq. NaOEt 2) O O O O NH2 O O O O O O 3) Mild H3O O O 3) Strong H3O /! O Count the carbons here! HO O OH + CO2 + 3HOEt Homework Problem Set 8 Iverson CH310N Due Wednesday, April 9 O N H * Racemic 1) Br 2) H3O (No heat) O N H /H N 1) O NH2 O N H * Racemic O 2) H3O (No heat) NH2 Cl 1) O 2) H3O (No heat) O O * Racemic N H ...
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