Compare Chloromethane and benzyl chloride

2007-11-07 9:37 am
Y Chloromethane undergoes SN2 Nu Subs slower than Benzyl chloride?
According to CClee Reference Book

回答 (1)

2007-11-09 9:17 pm
✔ 最佳答案
要Favor SN-2 type nucleophilic subsititution , 首要條件就是要attach住個halogen或其他high electronegativity既物質(例-OH)果個Carbon atom要連住大量low electronegativity既group(例如R-group)‧
明白了嗎 ? Chloromethane : CH3 - Cl ,當中個"C"並無連住其他R-group可以donate electron比Cl‧所以,CH3 - Cl => CH3(+) + Cl(-)既速度自然慢了(unfavour condition)
至於Benzyl chloride,當中連住-Cl既"C"左手邊同右手邊都有一條Carbon chain連住(R-group),所以果粒Carbon有兩個R-group可以donate electron比Cl,令C-Cl更polar => 令Cl更容易[甩]出黎,所以 : C6H5 - Cl => C6H5(+) + Cl(-)是較快(Favor condition)

最後補充一點 : R-group之所以是electron donating group是因為每一個"C"都連住2~3個very low electronegativity "H" atom,相比之下,一大串有H既R-group比只有3個H既CH3-Cl更易donate electron啦 ~

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