Explain how the structure of the alcohol (and thus the alkoxide base) affects th

Question

Explain how the structure of the alcohol (and thus the alkoxide base) affects the quantity of each elimination product formed. Compare the ratios of areas from each of the different alcohols used in lab to support this explanation. (You must compare the results from your alcohol to the class results for the other alcohols.

My alcohol was 2-butanol

Below indicates others results

Safari File Edit View History Bookmarks window Help Elimination Lab 308-008 Class Data - Google Sheets | | || | + | E] httpse docs.google.com/spreadsheets/d/1fwd71EWOF5kIAUQ24L8eCkhhFtfjZo0sORQSZTCwp44/edit#gid=0 Apple Pomeranian eeders.com Course Desc..es Program Reader Chegg Study Guided Solutions and Study Help I Che... myBoiseState | Student Elimination Lab 308-008 Class Data -Google Sheets Elimination Lab 308-008 Class Data chickard@lcmail.csc.edu . File Edit View Insert Format Data Tools Add-ons Help Last edit was made 20 minutes ago by anonymous Comments Share % .0 .00 123 Arial 187.32 None 202.1 Lots 202.24 Lots 1 2-butanol 2 2-butanol 3 Absolute Ethanol 4 Absolute Ethandl 5 Alcohol Used 6 ethanol 7 Isobutyl Alcohol 8 Isobutyl Alcohol 9 Isobutyl Alcohol 10 Isobutyl Alcohol 11 Isopropyl Alcohol 12 Isopropyl Alcohol 13 Isopropyl Alcohol 14 K t-butoxide 15 Methanol 16 perimental Data 611.03 696.3 332.16 310.5 295.61 335.3 631.8 487.5 Lots Some some (49.5%) 1875 some (49.5%) 1-heptene trans-2-heptene cis-2-heptene None/Some/Lots? None/Some/Lots? 308.2 267.75 440 581.4 598 1092 1120 1063.2 578.5 350.1 515.7 225 356 372 506.3 520.18 609 1116.95 300 510.5 Some Some (47%) some some Some lots some Lots 1050 Lots 115 Some 168 some 202.5 some 452.1 None 1028 some 1064 lots 555.56 Some 128.5 Lots 321.75 Some Some Relative Amounts of: Peak areas (mm*2) of each isomer formed SN2 Products Starting Material 20 23 Shee

Explanation / Answer

In E2 elimination reaction a beta proton is eliminated along with the leaving group (usually a halide). The beta proton which has a greater number of substitution is favored over a less substituted proton. however if a bulky base is used, approach of the base to the reaction center becomes diffucult and a elimination of a proton which is less crowded (less substituted) is favored.

If you use ethanol, the base is ethoxide and if you use 2-butanol, then the base is 2butoxide. 2-Butoxide has a larger size compared to ethoxide, so it will favor the formation of alkene with less substitution.

Similar trend is observed with other base also. Elimination of less substituted beta proton gives 1 heptene as product whereas more substituted beta proton elimination gives a (cis/trans) 2 heptene. As the size of the base is increased the relative amount of 1 heptene formation is increased.

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