Part Four: Multi-Step Reactions and Synthesis to cycl 6. Predict the product of the following multistep reactions: он 1) PBr30°C 2) mg, ether 3)2 4) Hạ, H2O 5) PCC, CH₂ Cl₂ ? clonekane into 2-c 1) Br₂, hv 2) Mg, ether 3) ня 4) HCI, H₂0 5) H₂SO4, A 6) Zn (Cu), CH₂ I₂ ?
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- Provide the structure(s) of the expected major organic product of the reaction shown. 1) Disiamylborane 2) H₂O₂, NaOH OI O II ||| O IV OV CH3CH₂C(CH3)2C=CH OH OH xx xo IVThe following series of reactions will yield 2) CI-CH2-CH2-C6H5 1) CH3CH2SH + N2OH O 2-chloro-4-ethyl-benzenesulfonic acid O CH;CH2-S-CH2CH2C6H5 O ortho-chloro-ethyl-benzene O 1-phenyl-3-chloro-propane O CH3CH2-O-CH2CH2C6H5Complete the starburst scheme below by predicting the product of each reaction. CH2N2 HBr Og then Cl2 Me2s Pd/C H2 BH3 then NaOH, H202 Me Br2, MeOH MCPBA DCM CH;OH H2SO4 OsO4 then H2S Hg(OAc)2 H20 H2SO4 |H2O2, A HBr
- Br Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:The third part of the synthesis is occurring on P=O, which has a similar reactivity as C=O. NO2 HN-P-O Pho CI CI но 10 Ph NH2 11 NO2 4a. Propose a synthesis of racemic 9. For each step, the reactant, condition and product must be clearly shown. No mechanism is required. The reagents are limited to: Any organic compound with one/two/three carbon(s) AND one functional group; Any inorganic reagent, such as H20, HCI, NH3, KCN, CO2 etc.; Any non-building block, such as acid, base, catalyst, protection reagent, redox reagent and solvent. Organic compound with 1/2/3 carbon(s) AND one functional group Inorganic reagent Non-building block NH; racemic 9 4b. Draw the structure of compound 10.1. Draw the structural formula for the major product of the following reactions. (a) OH 1) SOCI2 2) NH3 ET2NH (b) Br 1) Mg, ether 2) CO2 3) H3O* (c) CN H2SO4 (d) H2O H2SO4 (e) он он
- Which of the following is the best method to carry out the following transformation? OH (a) H₂SO4, H₂O (b) 1. BH3 2. H₂O2, OH (c) 1. Hg(OAc)₂2 H₂O 2. NaBH. (d) 1. HBr 2. H₂ON3 H Predict the product of the following multi-step reactions. The points per question is the Number of Steps + 1 (2 steps = Show the intermediate of each step for partial credit considerations. NaH, then Br 1) Ph3P, H₂O 2) CH3l (3 eq), then Ag₂O 1) NaOH, 12 2) NaNH2( 3 eq)CS41 10.) Chapter 7: E2 SNI + EI SN1+ E1 Mechanisms. Using correct mechanistic arrows, provide the step-by-step mechanism that demonstrates how the following reactions proceed to afford both substitution and elimination products via SN1 and E1. You do not need to show stereochemistry while providing the mechanism, but show correct stereochemistry in the final product(s). If there is more than one product feel free to write +E or +D as appropriate (or just write your products). C341 Br CH3NH2 CH3CH2OH CH₂OH Br CH3CH₂OH A Page 5 of Chapter 7: E2 SNI + E1
- Predict the dehydrohalogenation product(s) that result when the following alkyl halides are heated in alcoholic KOH. When more than one product can be formed, rank them in terms of their predicted stability (1 is most stable isomer, 2 the next most stable isomer, etc...) a) b) HD HD H CH3 ''CI H CH3 Br 'Br KOH EtOH KOH EtOH KOH EtOHWhat is the correct sequence of steps for the following transformation? Step 1 Step 2 HO (a) HBr, followed by H20 (b) H2 over Lindlar's catalyst, followed by H2O/H,SO4 (c) H2O/H2SO4/H&SO4, followed by HBr (d) H2 over Pd/C, followed by H20 Which structure corresponds to the missing step in the reaction mechanism for the conversion of the alkene/alcohol to the cyclic ether? HC! H20 + H;O OH OH OH (a) (b) (c) (d)Please fill in the blanks!! Which set of reagents (given below) would produce the products given in the following reaction? A Br₂, hv F NBS K heat B Br₂, DCM G H₂, Pd C HBr, DCM H Br₂, H₂O L Grubb's D HBr, H₂O I KMnO4 M CH₂l₂, Zn E HBr, H₂O₂ J 1. Li, 2. Cul