tb23 - Chapter 23 Carbon vi Condensation Reactions Draw the...

Info iconThis preview shows pages 1–5. Sign up to view the full content.

View Full Document Right Arrow Icon
Chapter 23 - Carbon vi Condensation Reactions Draw the structure of the aldol self-condensation product for each of the following compounds. If a compound does not undergo aldol self-condensation, explain why it does not. 0 " 1. CH3CHCH2CH I CH3 Answer: 0 II CH3CHCH2CH= c- CH I I CH3 CH(CH3h 0 2.~ UU Answer: Benzophenone does not undergo aldol self-condensation because it has no a-hydrogens. 3. 0 ~CH3 Answer: 0 CHO I 3 II 4. HC-C-C-H 3 I CH3 Answer: 2,2-Dimethylpropanal does not undergo aldol self-condensation because it has no a-hydrogens. 254 Chapter 23: Carbonyl Condensation Reactions
Background image of page 1

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

View Full Document Right Arrow Icon
Consider the reaction below to answer the following question: 0 0 H NaOEt ~ EtOH 0 crH + H2O 5. Write the complete stepwise mechanism for the reaction above. Show all intermediate structures and all electron flow with arrows. Answer: "~II ~:§F1 0 n ~o "~" 6. This reaction is an example of: a. b. c. d. an intramolecular Claisen condensation an intramolecular aldol condensation a Robinson annulation a Michael reaction Answer: b 7. The product ofthis reaction is: a. b. a f3, r-unsaturated aldehyde a a, p.unsaturated ketone an a, p.unsaturated aldehyde an enol c. d. Answer: c Test Itemsfor McMurry's Organic Chemistry, Seventh Edition - - 0 cj'" .. i :OEt ce o ar .~H 0 H - H §JVOB u" 255
Background image of page 2
Consider the data below to answer the following questions: The Friedlander Quinoline Synthesis, first reported in 1882, is the base-catalyzed condensation of 2- aminobenzaldehydes with ketones to fonn quinoline derivatives. 0 ~ 0 J R ?" H 0 ?" ~ R' ?" ~ oC + RCH,~ ~ ocf ~ OCX ' NHz NHz N R' 8. The first step of the Friedlander Quinoline Synthesis is a mixed aldol condensation. Write the complete stepwise mechanism for this reaction. 0 ~H fi ~"II.TU + RCH2CR' NH2 ~~ ~"II.TU_i NH2 base . Answer: ~R' U~ID_~ t NHz to t ",,!'}!,,;;, ° cjH a CJC; r'H -,- R cxY R' ~ R' I ~qICR'-' I R -. I R H ~ NHz ~ NHz ~ NHz ~~base 0 II - !r:R' )baSe 9. The second step of the Friedlander Quinoline Synthesis is a nucleophilic addition of a primary amine to a ketone yielding an imine. Write the complete stepwise mechanism for this imine fonning reaction. Show all electron flow with arrows and show all intennediate structures. ~~ ~"II.TU_i NH2 base. ccc R -:? ~ I ~ ~ N R' 256 Chapter 23: Carbonyl Condensation Reactions
Background image of page 3

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

View Full Document Right Arrow Icon
0 I 6 0 , ~. 0 :0: / 6 NaOEt 6 0 - \ erR ~EtOH R-X . Answer: ~ 0llJR ~ R ((X I ~ 0:- ~ + 00 N / \ R' H H ro R -:? ~ I ~ h N R' i (X)C R -:? ~ It transfer I 0'OH .~ ,3 R' H '-.Jbase 10. In the alkylation of cyclohexanone, better yields are obtained by first reacting cyclohexanone with an equivalent of lithium diisopropylamide in THF and then adding the alkyl halide, rather than mixing cyclohexanone, alkyl halide, and a catalytic amount of sodium ethoxide
Background image of page 4
Image of page 5
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

Page1 / 17

tb23 - Chapter 23 Carbon vi Condensation Reactions Draw the...

This preview shows document pages 1 - 5. Sign up to view the full document.

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