Quiz 6 - N NH 2 HN NH 2 10.37 9.13 4.49 2.16 CO 2 H CN NH 2...

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
MCMP 205 Friday, April 10, 2009 20 pts Name __________________________ Lab TA _________________________ Lab Period ______________________ Quiz 6 1. (2 pts) The pKa values associated with piperazine (structure below) are 5.68 and 9.82. Draw the structure of the major species that exist when piperazine is dissolved in an aqueous buffer at pH4 and at pH 7.5. HN NH H 2 O pH 4 buffer HN NH H 2 O pH 7.5 buffer 2. (2 pts) The amines listed below have pKa's of 2.16, 4.49, 9.13, and 10.37. Write the correct pKa values in the space below each compound. pKa NH 2 O OMe NH 2 OMe MeO NH 2 O CH 2 NH 2 5 MeO O 3. (6 pts) Predict the major product from each of the following sequences of reactions. a) CO 2 H 1) H 2 , Pd/C or Sn, HCl 2) HNO 2 , HCl 3) CuCN, warm b) Br 1) NaCN 2) LiAlH 4 3) aqueous acid workup 4) neutralize with NaOH NO 2 c) 1 H 2
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: N NH 2 HN NH 2 10.37 9.13 4.49 2.16 CO 2 H CN NH 2 1) SOCl 2 2) NH 3 3) Cl 2 , NaOH, H 2 O OCH 3 H 3 CO O OH OCH 3 H 3 CO NH 2 Name __________________________ 4. (6 pts) Using curved arrow notation write a stepwise mechanism for the transformation of A and B to C . OEt O O O NaOEt HOEt OEt O O O 5. (4 pts) When C is heated in aqueous acid it is transformed to compound D . Reductive amination with dimethylamine gives compound E . Provide the reagents and draw the structures of the intermediates for the convertion of E to compound H by the Hofmann elimination. A B C O O D Me 2 NH, NaCNBH 4 pH 4 buffer N N E E F G G heat H 2 N N MeI I-I-N N HO-HO-Ag 2 O-OEt OEt O O + HOEt O OEt O O O H-OEt 2 pts for structure, 1 pt for arrows 2 pts for structure, 1 pt for arrows...
View Full Document

Page1 / 2

Quiz 6 - N NH 2 HN NH 2 10.37 9.13 4.49 2.16 CO 2 H CN NH 2...

This preview shows document pages 1 - 2. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online