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Lecture

4 Substitution vs. Elimination.docx

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Department
Chemistry
Course
CHEM 212
Professor
Ariel Fenster
Semester
Summer

Description
Substitution vs. Elimination SN2 and E2 reactions both are favoured by a high concentration of strong nucleophile or base. Substitution occurs when the nucleophile attacks the carbon which has the leaving group. Elimination occurs when the base attacks a β-hydrogen. Industries that prefer one reaction over the other often need to control the reaction as to produce the favoured reaction. Mechanisms – + OH + H2O + CH C3 I 2 + H2O + CH CH I + CH =CH 3 2 2 2 Data 2 Table 1: Chemical Quantities Name Formula Molecular Amount (g) Amount # moles weight (mL) g/mol -6 Ethyl iodide C2H 5 155.97 n/a 8.0x10 n/a (800μl) Ethyl Ether C H O 74.12 10 4 10 Ethanol CH 3H O– 46.04 2 2-naphthol C10 O7 143.00 5 2-ethoxynaphthalene C12 O10 172.22 n/a 2 Table 2: Chemical and Physical Properties Name Formula M.P (°C) B.P. (°C) Density Solubility Safety (g/cm ) Ethyl iodide C2H 5 -108 72 1.95 Slightly -corrosive Ethyl Ether C4H 10 -123 35 0.71 6.9g/100mL -flammable Ethanol CH CH OH -114 78 1.59 Miscible -irritant 3 – 2-naphthol C10 O7 122 285 1.22 -negligible 2-ethoxynaphthalene C12 O10 37 282 1.06 in water Melting point of 2-naphthol: 122°C Melting point of 2-ethoxynaphthalene: 37°C Melting point of product: 32-34°C Yield in grams: 0.220g Discussion This experiment is a synthesis by nucleophilic substitution (S 2N since the melting point of the product obtained was fairly close to that of 2-ethoxynaphthalene. Since it was slightly lower and not exact, this indicates sli
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