Question

Use this table to correlate the peaks in the GC printouts to product identification. Then use the table entries for area or area% in the GC results to calculate ratios. The Nucleophilic Medium contains: RT (min) Compound RT (min) Compound 2.06 1-butanol 2.34 1-chlorobutane 1.35 2-methyl-2-propanol 3.04 1-bromobutane 1.68 2-chloro-2-methylpropane 1.75 2-butanol 2.14 2-bromo-2-methylpropane 2.09 2-chlorobutane 2.70 2-bromobutane Note: Deviations for RT are approximately + 0.07 100g ice 76 mL conc. H2SO4 19.0g NH4CI & 35.0g NH4B GC Chromatography Traces 1.346 1.693 2.130 RT AREA TYPE WIDTH 1.69371239BB 014 2.130 66862 BB 012 AREAX 51.58472 48.41530 OH 1.748 - 2.088 2.705 - RT 2.088 2.705 Area 56310 194360 Type Width Area% BB 0.019 22.46380 PB 0.019 77.53619 1.735 2.073 RT 2.360 3.045 Area Type Width 24016PB 0.018 190167 PB 0.018 Area% 11.21284 88.78717 MOH

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Identify the mechanism for each substrate and explain your decision based on reaction theory. Would you expect the primary, secondary and tertiary substrate to react SN1 or SN2? How do the experimental results confirm your choice?

Answer 1

Reaction 1 From G&T = 1.35 Since ree fate of the reaction depends upon the nature of the nucleophie; The reaction proceeds through Se reaction me chamom SN² reaction mechanism n - OH H250 Br RT = 2.14 RT = 1.68 t (BC Lotte Cool Ton via the formation of for an exothermic reaction. 3° Alcohol and. 3 Carbocation, thbinet reaction rate depends upon both the nucleophie and the leaving group. > edt Reachomt from ho Area under the peak = 71 239 (51.58% (CB)3c-u. for. reach Co-ordinak Area under the yeak (CBC-Br. 66862 (48.42 / reaction proceeds through SNL reachon mechan nism , where the step-1 the formation of Casson Cation is the rate determining step (rds). Leaving group is same for are both lases. SN realsion for an (CH),ct oney involved exothermic reaction " (012) 3-c-OH combined combined a) The alcohol is a secondary alcohol. 6 The Carbocation is moderately stable. @ SN and Sw? both are moderately possible. (d) Br" ion is a good nucleophile therefore. Bromo product obtanined Predominantly over Chloro, because SN2 reaction is mechanism. is involved. 9 € Snor both culoro and bromo Pdt must be obtarined almost in equal rasion amount se lil but here the round the rano of chloro and bromo paht is = 22.5177.5 indicating both ) SN and 3N² reaction mellianism involue Primary alcohol n OH SN² sor@ RT =) Area Areay. 2.360 24016 11:21 =) o e . 3.045 190167 88.78 The reaction proceeds through Sy reaction mechanism only =) SN2 mechanism more favorable TO favorable SN? mechanism proceeds over SNL little more preferentially with - Reaction Co-ordinate.. Br- is softer than cư therefore Brattack the Carbocahon better than cé to form ( C C By little more them Ston (CA), c-u. tack te Ba ② 2-Butanol = RT =) 1.693 (Huoretical) 1:75) & coB-CH-CH2-City - 2109 - 22:57 CH-CH-che-clay =) 2.71 = 77.5% Br is a better nucleophile than e- 30