1. Determine whether the following reactions will go through SN1, SN2, E1, or E2 mechanism a....
describe each as Sn1, Sn2, E1 and E2 then draw a curved arrow mechanism for each reaction. NaSH DMSO SH KOH HO DMSO Br NANH NH3 OTs NH TsO TsO CHs CH3 Nal CH3 acetone CH O O
1. Determine whether the following reactions go through SN or SNP and write the products, with stereochemistry as applicable. BrNHz NaOEt Nal OMS KCN CI DMSO Br HO NaSH DMSO Tso CH3 Nal Acetone CH3 2. The following reactions each undergo SNmechanisms. For each explain why you would predict the substitution products to come from an SN2mechanism and fill in the product. If stereochemistry is given in the reactants, give the correct stereochemistry in the products. Cl + Z Na...
Practice Problems on S, S2 E1 &E2 1. Describe the ollowing chemical reactions as Sl, S2, El & E Draw a curved arow mechanim for each resction CHCHO N ethanol NaSH DMSO SH Кон но DMSO NaNH2 NH3 отв NH3 HN TsO TsO CH CHg Nal CHs acetone
2. Predict which reactions proceeded by an SN1, SN2, El or E2 mechanism: NaOCH-CHa Br оСнCH +NaBr носH-Cнь 50° b. +NaCi Nal DMSO, 45° NaOCHa NaBr +HOCH носн, 100° но +HI acetone, 50 HSO +H2O H2O, 120 кос(CHa +KBr +HOC(CHals НоС(CHа, 100°С но DMSO, 40° +HI HCIZNCI2 +H2O h. H,O, 45° CH OH +HCI H2O, 100
For letters h & i : For each of the following reactions, predict the major mechanistic pathway (SN1/SN2/E1/E2) and the major organic products 1. (cont.) (h) НСОН CHB -CHBr HCOH - (0) CH,CH,CH,CH,Br- NH 2. For each of the following indicate which reaction will occur faster. Explain your reasoning. (No credit will be given for guesses) (a) The reaction of (CH),CBr with 0.001M aqueous NaOH or 0.10M aqueous NaOH (b) The reaction of 2-bromobutane with NaOH in DMSO or NaSH...
find products for the following interactions and identify the mechanism as sn1, sn2, e1, or e2 A) 2-Iodo-2-phenyl butane + water CH3-CHO-Na+ / ethanol B) 2-Chloro-2-methyl propane + СН3 H3C CH C) 1-Chloro pentane + Nal / acetone + Concentrated H.SO. (No Water added) -----> D) 2-phenylbutan-2-ol ОН 10 pts) E) Write a complete mechanism for Reaction D above Be sure to show the intermediate or transition state.
2. Predict whether the reaction willl go by SN1, SN2, E1, or E2, or some combination of these. Explain. Also give the products with correct stereochemistry if applicable. SoI Na CN Br dimethyl sulfoxide (DMSO) CI CH,онн,0 Br CH3S Na* + acetone
Complete the following reactions and state the dominant mechanism acetone b. (R)-2-bromobutane + Nash mechanism: c. (18,2S)-1-bromo-1,2-diphenylpropane methanol + NaOCH; mechanism: d. 3-chloro-2,2-dimethylbutane + NaSCH; mechanism: t-BuOH e. 2-chloro-2-methylpentane + (CH3),CONa H).CoNa BUCH mechanism:
7. Predict the product(s) of each of the following reactions include stereochemistry where important and indicate the mechanism (S, S,2, El, E2). 80°C a 2-chloro-2-methylbutane NaOH Н.о b. (R)-2-chloropentane Nac c-H DMSO с1 (снс. Cн, CH,ОН d. trans-1-chloro-3-methylcyclohexane+ NaOC(CH) e. 2-chloro-3-phenylbutane Н.о f. trans-1-bromo-3-methyleyclopentane Nal acetone NaOCH THон g 2-chloro-2-methylbutane EIOH h R-3-bromo-2-methylpentane . trans-1-bromo-2-isopropyleyclohexane CHCOK NaSH Н,о j. 1-bromopropaе NaOCH снон CH коссH). I-bromobutane m. cis-1-chloro-3-methyleyclobutane Nal DMSO сHсH,он n. (R)-2-iodo-2-phenylethane NaOH o. 1-iodobutane p. 2-bromo-3-methylbutane KOC(CH). но (S)-3-chlorocyclopentene...
CHE241/240 Assignment 2: SN2 and SN1 Name:Alexo.adio Hesker 1. Indicate whether the following substitution reactions will proceed by Sy or Sy? [3] Racemic NaCN DMSO 2. Draw a mechanism for the following Sy reaction? [3] SH + NaSH NASH - - NaBr + NaBt 3. Draw the transition state for the following Sy2 reaction? [3] 1. Indicate whether the following substitution reactions will proceed by SNP or Sn"? [3] MOH problemi CXCHANS H.0 NaCN DMSO 2. Draw a mechanism for...