Question

Complete questions 10-27

PART II: REACTIONS: Here is another different" question. Pretend you have been asked by me to put together a bunch of one-step reactions WITH starting materials (your choice), reagents and answers to help me with writing a final exam. For example: let's say I ask you to give an example of a free radical chlorination with a non-cyclic compound. Below would be your answer. As I am pretty sure you can figure out, there are millions of other possible correct answers. Nope, you need not pick a reaction that gives more than one product, but you could CH3CH2CH3 (substrate) + Cl2 (reagent) -> CH3CH2CH2CI+ CH3CHCICH3 (products, in this case) Got the idea? This is certainly different than our usual one-step reactions, but it is easier than what you would get on a "real" Orgo 2 final. One more comment: the example I have shown above is from Orgo 1. You are NOT responsible for last semester's reactions. I just used it as an example. Again, imagination combined with sound chemistry will run the show here. I know I said this before. Each of your answers below, just in case you didn't compute" above, MUST be in this format below; clearly, each one of your answers is NOT worth the 2 points al our other one-steps have been worth; this is a totally different animal, so to speak. Again, each answer has to look like this. Again, no sticks will be accepted, and no parentheses will be accepted. Saturated and unsaturated ring systems do not have to show all elements. We know this language by now. The clearer are your answers, the more points you will earn in each case. Again, your format is: SUBSTRATE + REAGENT -> PRODUCTS 1. A Grignard reaction with a substituted aromatic aldehyde 2. A reaction of a cyclic aldehyde with a specific strong oxidizing agent 3. An oxidation of a ketone with a specific strong oxidizing agent 4. A reaction of a branched primary alcohol to give an aldehyde 5. A reaction of your starting material in #4 to give a carboxylic acid 6. A reaction to prepare an alkyne using a metal acetylide 7. A 1,2- and 1,4 addition to a branched cyclic diene 8. A Diels-Alder reaction with a cyclic diene 9. A Diels-Alder reaction with ethylene 10. A halogenation reaction of a meta-directing aromatic 11. A carbonylation reaction with a sulfonic acid 12. An alkylation reaction of an o/p-directing compound 13. A nitration reaction of a secondary amine 14. A reaction of a primary aromatic amine with excess alkyl chloride 15. A reaction of a tertiary aromatic amine with a dilute strong acid (don't let the "dilute" part confuse you) 16. A reaction of your product in #15 with dilute strong base 17. A reaction of a trisubstituted phenol with dilute strong base 18. A reaction of your product in #17 with dilute strong acid 19. The reaction of a branched carboxylic acid with sodium bicarbonate (dilute) 20. The reaction of your product in #19 with dilute strong acid 21. The complete reaction to show the preparation of an aromatic ester from a branched carboxylic acid 22. The complete reaction to show the preparation of a non-aromatic amide from a cyclic carboxylic acid 23. An aldol condensation using an aromatic aldehyde 24. A mixed aldol condensation 25. A Claisen condensation using a non-aromatic ester 26. A mixed Claisen condensation using an aromatic ester 27. A malonic ester synthesis using two different halides, one of which is an aromatic

Answer 1

10. Halogenation reaction: N02 fe/BY-> Eur >102 m. Nitroben a che m-directing и 11. Carbonylatim reaction : - 4G) (Suffonic - CH₂ - C = CH₂ - acid) Не со mechanism : cb c = 0 1 H - (Koch reaction) CH Hçe - CH₂ 1co = 0 abg H2o 얘 BC CB & - 12. Alkylation reccetion : CH3 CH3-C E , ED Anhydrous • All o-xylene op directing 13. Nitration of Selendary amine: b-xylene N-Neo NH CH3 ICI NaNc2 Hel N - N- Nitroso -N-methyl -Nitroso -N aniune excess R-8L REWART 14. R-NH₂ : primary amine

is. WC - 3 HC-.HP dilute slang aud N,N-dimethyl (H-) qualernary ammonium salt aniline H₂ & 16. El a strong -Base (8) O + H20 # Tertiary amine regenerale when quaternary ammonium salt is treated with strong base 17. When tri substituted phenol is treated with strong base then phenoxide ion is formed. OH Nak R-TT RETR (Phenoxide ion)

18. Product formed in reaction 17, when treated with acid, Phienol is regenerated as a product. OH Na HA) 19.5 20. 20. when branched Carboxylic acid is treated with Shony base, then carboxylate ion is formed which on treatment With acid, Carboxy uc acid regenerales. (C+13) C - Looh Nach (CH₂), 600 na 4 (CH₃), C-Looth

21. - CH COOH Sou2 3 Soc₂. L =coch CH3 .o-ph 22. secas da cm), bangla bug 23. Aldol Condensation: het congueug moeten er meget product) nce เท่ 47 : Ć Hz~ E- CH₂ Way CH₃_E-cilla t i cha 24. mixed Aldol condensation 25. chaisen condensation ericus + entoe en helt ny ring - CH₂-Emoet Naoft edge che il moet mechanism : en, loht Naglet e fto-day was Elo-887 0,9-064 —> euen, -e-ft che et de oft t-tht Eto-d - > bet

26. mixed claisen Condensation: cycl_oct + BrloEt » Nackt > pole lot

27. Synthesis of substituted acid:- Etorth Koet Cho Na Eto the host C3-CH-B CH2=CH2=CH2-600H H1 Eto those (-662) a Eto t roet in Naoft Lot ii) E ncs