{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

ass8 - CHM 2120 Assignment 8 In this assignment The aldol...

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

View Full Document Right Arrow Icon
CHM 2120 – Assignment 8 In this assignment: - The aldol reaction - Haloform reaction - Synthetic applications Note : many questions incorporate earlier material 1. Draw the mechanism for the tautomerization of 1-phenyl-1-butanone (also known as butyrophenone and phenyl propyl ketone) under a. acid catalysis b. base catalysis Ph O Ph OH 2. a. What is the key tautomer of the molecule shown below? b. Which would be the major tautomer at equilibrium? Why? c. How could you prove the structure of the major tautomer by IR? O 3. a. Draw a mechanism for the generation of the compounds shown below. b. Describe how the 1 H NMR of the starting material would differ from the 1 H NMR of the two products. Note: H = 1 H barb2right detected by 1 H NMR (peaks are seen) D = 2 H barb2right not detected by 1 H NMR (no peaks) O NaOD D 2 O O O D D D 4. A solution of dimedone (5,5-dimethylcyclohexane-1,3-dione) in chloroform contains 33% of an enol tautomer. Draw this tautomer and explain why it is found in much higher proportion than most enols.
Image of page 1

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

View Full Document Right Arrow Icon
Image of page 2
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}