9. Tell whether each of the following reactions is likely to be SN1, SN2, E1, E1CB, or E2: NaN3 (a) CH3CH2CH2CH2B CH3CH2CH2CH2N=N=N Ether (b) CI КОН CH3CH2CHCH2CH3 CH3CH2CH=CHCH3 Ethanol (c) CI OCCH3 -CH3 -CH3 CH3CO2H (d) NaOH OH Ethanol
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- Determine whether each of the following syntheses requires a reaction that alters the carbon skeleton. (a) (b) OH (c) (d) OCH,CH3 CH3 (e) OH (f) H,CO он H;CO. (g) H3CO, (h) H3CO. NO2 NO2Which compound will undergo decarboxylation (-CO2) most easily when heated? (a) CO2H (b) НО-С HO2C CO2H (c) CO2H (d) CO2H CO2H ČO2H CO2HTell whether each of the following reactions is likely to be SN1, SN2, E1, E1cB, or E2: (a) CH3CH₂CH₂CH₂Br NaN3 THF CH3CH₂CH₂CH₂N=N=N (b) (c) (d) CI CH3CH₂CHCH₂CH3 KOH Ethanol -CH3 CH3CO₂H OH NaOH Ethanol CH3CH₂CH=CHCH3 요 OCCH3 -CH3
- Tell whether each of the following reactions is likely to be SN1, SN2, E1, ElcB, or E2: (c) CI OCCH3 CH3 CH3CO2H -CH3 (d) NAOH OH EthanolOH - NH, Br2/KOH →product; 1. (a-hydroxy amide) Product of this Hoffmann bromamide reaction is : OH (a) Ph – Ĉ-CH3 (Ъ) Ph — CHO (c) Ph- CH3 (d) Ph – CH2 -NH2 NO2Which of the following compounds is the major product of the reaction sequenc shown below? (1) Na CNCH3CN Br (A) (B) NH2 (2) H* H20, A он (C) (D) HO. O Compound C )Compound A Compound D )Compound B
- 2) Identify whether each of the following reaction performs a SN1, SN2, E1 or E2; Then, draw the appropriate products. Meo (a) NH2 (d) Br Br он (b) (e) ELOH HO Br (c) (f) BrPropose a plausible mechanism for the following transformation and justify the stereochemical outcome (J. Org. Chem. 1999, 64. 4617-4626): CO₂Me Heat MeOH MeO ° CO₂Me Step 1 Add any remaining curved arrow(s) to draw the first step of the mechanism. H₁₂C H.C ་་་་ H₂C O-CH3 Edit Drawing CH₂9a) The proton bonded to the carbon adjacent to the carbonyl group in the following compound can be classified into which chemical shift in the ¹H-NMR spectra of aldehydes and ketones? R or H H - 10.0-12.0 ppm R H -2.0-3.0 ppm NO₂ N (1) 9b) Choose the one below that could be resolved into enantiomers. (1) alpha hydrogens = ? ppm NO₂ NO₂ 9c) Which of the following is the major product of the reaction below. `N H -5.0-7.0 ppm (11) (11) -0.0-1.0 ppm HNO3, H₂SO4 H NO₂ (III) NO₂ (1) and (II) (IV) None of the options (IV)
- Predict the major product(s) for each of the following reactions. Show both enantiomers if a racemic mixture is formed: ? ? 1) RCO₂H 2) H3O+ HBr 1) BH3⚫ THF 2) H2O2, NaOH ? ? H2, Pt Br2 ?Name the following alkyl halides: (a) Hас Br Br CH3 (b) I (c) Br CI CHз CH3CHCHCHCH,CHCH3 CH3CH=CHCH2CHCH3 CH3CCH,CHCHCH3 CH3 (d) CH2BR (e) CICH2CH2CH2C=CCH2B CH3CH2CHCH2CH2CH3When propenal is treated with sodium acetylide, a product is formed whose IR spectrum exhibits a broad absorption between 3200 and 3600 cm¯1, but shows no absorption near 1700 cm-1. (a) Draw the structure of the product. (b) Argue whether the nucleophile adds reversibly or irreversibly to the carbonyl group. CH HC || CH2 1. HC=CNa ? 2. NH,CI