Please attach additional pages as needed for your solutions to these problems. Keep in mind that the answer on the key is not the only possible synthesis. I will be happy to evaluate the ones that are submitted upon request if they differ from mine. O ok to use phenol ОН H. Br HO
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- 1. Rank the following molecules in terms of increasing acidity. Explain your rankings in terms of stability of the corresponding conjugate base. OH HO, SH NaNH2 =H HO,Predict the product for the following reaction. H₂C A I and II HH3C xoxoxox B D IV E cis-1-bromo-3-methylcyclohexane ||| SH H₂C NASH III acetone Br H3C ||||SH IV Heq eq M M M ereg 2req 2req 2req X 2req J F3 $ 4 R C V [Review Topics] [References] Draw both resonance structures of the anion formed by the reaction of the most acidic C-H bond of the compound below with base. 4x Include all valence lone pairs in your answer. • For structures having different hydrogens of comparable acidity, assume that the reaction occurs at the less-substituted carbon. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate resonance structures using the symbol from the drop-down menu. ✓✓99.81 O 0- F4 . % 5 T G B F5 *** ^ 6 Cengage Learning Cengage Technical Support Y ChemDoodle H N F6 & N& 7 U O J F7 + [ ] در M 8 PrtScn K F8 9 Home O 83°F Sunny F9 L ) 0 End F10 P Previous C PgUp F11 9 ? Next Save and Exit 9:38 AM 7/18/2022 PgDn F12 0 Ins D Back
- A synthon is a concept in retrosynthetic analysis. It is defined as a structural unit within a molecule which is related to a possible synthetic operation. Example: OH bond breaks here synthesis Br + retrosynthesis NEC Na -NaBr Synthons C-C bond formation synthetic equivalents Br D=00 CN OH || ⒸC=N H₂O, H+ hydrolysis do not exist exist functional group transformation Common synthons: C1 synthons: carbon dioxide, carbon monoxide, cyanide, formaldehyde C2 synthons: acetylene, acetaldehyde C₂H4OH synthon: ethylene oxide OH Carbocation synthons: alkyl halides, carbonyl C Carbanion synthons: Grignard reagents, organolithiums, malonic ester/acetoacetic ester, terminal alkyne Use the synthons listed above, propose how you would synthesis the following molecules:X app.101edu.co I UL Week 7: Panonto CH3Br ||| DII Br || 4x X UL LTU 7-1A F4 Rank these alkyl halides in order of decreasing reactivity in an SN2 reaction. 4 Br F5 40 X Question 1 of 24 F6 O C|Chegg.com S F7 A) III < | < || B) || < | < ||| C) ||| < || < | D) | < || < ||| E) | < ||| < || PrtScn X + FB Home F9 A End F10 Tp S # ENG @ 10 PgUp 611 0 Show 10/Organic Chem 1 Week 5 Lab- Student.docx - Saved to this PC - P Search shiku sign Layout References Mailings Review View Developer Help OFir A Aa Ao AaßbCcDd AaBbCcDd AaBbCc AaBbCcD AaB & Re A == Ev vv 1 Normal 1 Heading 2 1 No Spac. Heading 1 Title A Se Paragreph Styles Editi 6. In an organic chemistry lab, chemists were attempting to convert compound I into compound III via a substitution reaction. To their surprise, compound II was the only obscrved compound after treating compound I with cyanide. :CEN : CN CI CN observed not observed a. Provide a detailed, stepwise mechanism for the transformation above that accounts lir the formation of pruduct II. Use the curved arrow lurmalism to show the tlow of clectroLs. Shew all lene pairs, intermediates, formul charges, und pertinent resonance structures. rited States l n Fa Accesibility: Inwestigate lext Predictinrs: O D' Fucus 99+ ** F10 F11 PrtSc F12 %23 3 4. 8 E T. Y G H J K C M Alt Ctri V N
- Rank the following acids in decreasing acidity. Explain your answer CH2ClCOOH, CHCl2COOH, CH3COOHIn each reaction box, place the best reagent and conditions from the list provided. 1) Br 2) 3) 4) DEET (the active ingredient in over the counter insect repellant) 5) Answer Bank Mg, Et,0 HN(CH, CH, ), (1 equiv.) H,O* CH,COOH CH,CH,NH, CH,CH, Br NH(CH,CH,),(2 cquiv.) НСООСH, H,CO НСООН CH, CH, OH NaCN NaNH, Br,, FeBr, SOCI, CO,The reaction shown below yields the given product. True False OH + NH₂ DCC NH₂
- b) Rank the following alcohols from the most to the least acidic. (liic. НО. CI I но. I || Н ОН I HO CHO H3C-C-CH3 H-C-н Н CH3 " ОН ОН IV c) Indicate the oxidation state for each of the carbon atoms highlighted in red. v. НО F F H-O-OH H₂C-C-H н-с-он V ОН H3C-"-н H3C-C-CH3 ОН IV VComplete the synthetic sequence below by providing the structures of the reaction (questions 7-8). 1 mole of HOCH,CH,OH/H > B 1. LIAIH, 1.03 H* 2. Zn/H 2. Н.О. What is the structure of B? HO. (A) (D) OH\/C)0.Bm HB 4 1. What reagent can be used to form the product in each of the following? но | || H-C-C-H Н WA Н- нон -C-C-H Н Н нно -С-С-С-О I Н Н — - - - HO H-C-C-OH H H OH H | | | H-c-c-c-H | | | Hнн HHO H-C-C-C-H Н Н What is the product of this reaction? H OH H-C-C-CH3 H2CRO4 H CH3 What is the name of the bond formed when methanethiol is oxidized? CHz-S-H + H-S-CH3 — CH-S-S-CH3 + H2O Identify the acetal and hemiacetal functional group in the following OF CH охо OH OPE Guitkwot И www CH₂ OH H ко Calculate the molecular formula for each of the following. 985 НО