有機化學合成

2008-12-27 7:24 am
試解釋以下反應中試劑的用途...
1.CH3CH2CH2CH2NH2–{CH3I}→CH3CH2CH2CH2N(CH3)2
2

圖片參考:http://hk.geocities.com/stevieg_1023/03.gif

回答 (2)

2008-12-29 7:09 pm
✔ 最佳答案
Q1. let CH3CH2CH2CH2=bu,
BuNH2- + CH3I ---> BuNHCH3
second step
BuNHCH3 + CH3I ---> BuN(CH3)2

BuNH2- is the nucleophile.

Q2. hofmann rearrangement. out c in HKALE chemistry. it has the following steps,

1.RCONH2 + OH- ---> RCONH-
2.RCONH- + Br2 ----> RCONHBr + Br-
3.RCONHBr + OH- ----> RCONBr-
4.rearrangement:
RCONBr- ---------> R-N=C=O + Br-
5. hydrolysis
R-N=C=O + H2O----------->RNH2 + CO2
2008-12-28 1:44 am
我記得呢d好似係AL CHEM, 我試下答啦
好開心見到咁高層次的問題呀~~~

1. CH3I 係一個nucleophile provider. I 會有 delta - charge, H adjacent to N has delta + charge. I attacks H and N attack CH3 adjacent to I. They exchanged their partner. CH3 has a strong electron-donating nature than H and N has a higher electronegativity than I so that they exchange for their better match.

Is that right?

For Q2, I think it is a Hoffmann reaction and was taught in the amine chapter, according to my memory.
I am not sure about the answer, but I remebered that there are CO2 formed.
May be.....
The nucleophile OH- attacks the central delta + carbon and the carbon withdraws from benzene and NH2, forming CO2 and go; at the same time NH2 gained electrons from the central carbon and get - charge. It will attack the benzene???

Actually, I dont know about the mechanism...

I am just feel interesting about your questions.

Keep going on posting! I will keep attention to these advanced questions.

I will search more information to enrich my answer next time (because now I am doing my homework =.=)

2008-12-27 17:44:56 補充:
Actually I love organic synthesis very much.
It is my favorate in Chemistry.
Nice to se these questions here.
Thanks Doctor.
參考: AL chem


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