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explain part A by drawing all the resonance structures for the four compounds. don't use mesomeric effect. which is not covered in chapter 15-chapter 17 from Organic Chemisry by Loudon 6th edition
![A) Rank the following molecules in order of decreasing rate of SN1 Solvolysis (1 is fastest, 4 is
slowest). Briefly explain.
CI
H3C
I More H₂ve
]
O
O₂N
OH
MeO
Rank the following indicated alcohols in the below molecule in order of decreasing rate of
oxidation with MnO2 (1 is fastest, 3 is slowest). Briefly explain.
OH OH
00
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- 9. The four compounds listed below undergo SN1 reactions at increasingly faster rates. For each compound, provide the contributing resonance forms for the carbocation intermediate that would be formed. Explain why the resonance forms provide information about the rate differences. Br eloo esnsib to0 018-terl (V-) woled bew Br TII ỌCH3 VI Br efin 8 to muloage AMA H ar ni ese of oaqe uoy bluow 6uleot iedW 8 Snoltone gaiwollot erl of 18 Br oubog toom) (blsitrwob) blall wol ta anoloiq olemots yino ed bluow enerfT A Jolduch.a.ed.bluow.nodhsa.ailysad ad no anotong onl tot leipie enT 8 Jolght s od bluaw anoioiq lytom er tot lenpie erdT Jolduob s ed bluow anoto anegotbyd S yino not olsigatni bhiow anolong lydlam arl hol langiae enT3Complete the following reactions schemes by drawing the messing intermediate/products: SeO2 i) Ethanol H* ii) H20 OH HỎ OH 1) 4 equivqalents of H2/ Pd iii) 2) KMNO,/H* O3 iv) Zn Ag,O/ H2O excess Mel K,CO3 Нeat v) CH36. For each reaction indicate the predominant mechanism: S,1, S,2, E1, or E2. (a) (b) (c) OH H* H* H* ? ? ? A. A OH OH (d) Br (e) .CI NaBr CH,OH DMSO dilute (CH),COK (9) OTs ? OTs (CH),COH Ethanol
- 122. For the following three step conversion of A to B, the appropriate sequence of reactions is A OH CAREER ENDEAVOUR B CHO (a) MnO₂; (CH₂OH),/p-TSA; PCC (b) PCC; MnO₂; (CH₂OH)₂/p-TSA; (c) PCC; (CH₂OH)₂/p-TSA; Jones' reagent (d) Jones' reagent; (CH₂OH)₂/p-TSA; MnO₂.Considering stereochemistry, draw the resulting E2 elimination product when H. is removed. H a Ho III.... H H₂ I jº ·*||||| H X Ś my è6. Complete reaction scheme below indicating reagents, catalysts and conditions, and side product trigil bezinslog si6101fon 290b 1l (b Senines levirba 6 gaubong nasamots gniwollot ads to doinW 01 sniowl (6 CH3 40 CH3 Scansgowi (d Ege nodie) ( nsgyxo (b NO₂ 19m02 2i gniwollet sits to mainW II HO
- 1. Write the correck IUPAC nemes Far the Foilawing organic comPounds: Br CH3 H3C 8. Assign E an or Z configuration bi CI 2. CidssiFy the Following reagents cs either nucleaphiles or e lectraph:les: Zn, CH3NH2, HS, OHa, CH3COOH, HoSO 3. Whet are the products obtained From the addition of HBr to each of the falbuing compounds? CH3 a) + HBr > CHo +HBr- 2.5. Can you write out the mechanism for the reaction below (note: cyclic brominium ion intermediate) Br H Br/H2O но H H3C BrP CHE 124 ORGANIC CHEMISTRY TUT2 2020 (Prote on Failed) Mailings Review View n and might be unsafe. Click for more details. Enable Editing 2. What are the major products obtained from the following reactions? Indicate the geometry (cis/trans). HBr, CH,COOH 近 91 81 61 L. 5. 8. 6.
- Consider the following overall reaction, which will be discussed in Chapter 20. H,C-CEN NH3 HOO H,C Below is a proposed mechanism for this reaction. Use the rules we learned in this chapter to evaluate whether each step in the proposed mechanism is reasonable. For each step that is not reasonable, explain why. :ÖH () H,C-CEN: H3C OH OH (i) + H,C H3C OH OH (ii) H,C H,C OH (iv) + H,O: H,C H,C OH (v) H3C H3C OH H. (vi) :NH, NH. H,C H,CProvide the mechanism and product(s) of the following reactions: O₂N. CI NaOH da /NH 1. KNH₂ 2. H₂O Br2, FeBr3 NaOMeWhat will be the major product of the following reaction and what is the likely mechanism for its formation? (CH;);COK Br racemic OCCCH3)3 OCCH3)3 ÓCCCH3)3 A B C D E