Within each structure, rank the indicated nitrogens by increasing basicity. Explain all (guide line: Increasing basicity. Begin by identifying the classification of the nitrogen.) nicotine N-G HN (d) LSD CH₂0. CH₂ HN cyamemaine, an anti-psychotic drug atabrine (anti-malarial) amb abist? ipsapirone, an anxiolytic drug

Organic Chemistry
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Chapter20: Carboxylic Acids And Nitriles
Section20.SE: Something Extra
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Within each structure, rank the indicated nitrogens by increasing basicity. Explain all
(guide line: Increasing basicity. Begin by identifying the classification of the nitrogen.)
(b)
nicotine
cyamemaine, an anti-psychotic drug
Pentenyl
cation
Pentenyl
anion
(d)
HN
LY
(a) C₂H₂CH-N-C,H,
LSD
CH₂0.
Which of these belong to MO of Vin ,t-pentadienyl?
Ponlenyl
radical
CH₂
H
(e) CH-C)
HN
utabrine (anti-malarial)
ipsapirone, an anxiolytic drug
8888
81818
- Which of these belong to HOMO in ,,-heptatrienyl radical? And how many electron/s it
has?
two e,
one e
two e,
one e,
- Construct a qualitative MO diagram for the following systems and discuss how the MOS
are modified by addition of the substituent (each ¹ mark)
a) CH=CH-CH=CH compared to CH=CH-CHO Acrolein (propenal)
NET₂
NHỊCH,
b) CH=CH-CN compared to CH=CH-COOH
c) CH=CH-F compared to CH=CH-NH
- Comparing FMO of the given compounds with each other while doing reaction with a
nucleophile and electrophile
a) CH=CH-CH=CH, compared to CH=CH-CHO Acrolein (propenal)
b) CH=CH-CN compared to CH=CH-COOH
c) CH=CH-F compared to CH=CH- NH
- Predict the energetially preferred site of protonation for each of the following molecules and
explain the basis of your prediction.
NEL₂
(d)
-NH₂
Transcribed Image Text:Within each structure, rank the indicated nitrogens by increasing basicity. Explain all (guide line: Increasing basicity. Begin by identifying the classification of the nitrogen.) (b) nicotine cyamemaine, an anti-psychotic drug Pentenyl cation Pentenyl anion (d) HN LY (a) C₂H₂CH-N-C,H, LSD CH₂0. Which of these belong to MO of Vin ,t-pentadienyl? Ponlenyl radical CH₂ H (e) CH-C) HN utabrine (anti-malarial) ipsapirone, an anxiolytic drug 8888 81818 - Which of these belong to HOMO in ,,-heptatrienyl radical? And how many electron/s it has? two e, one e two e, one e, - Construct a qualitative MO diagram for the following systems and discuss how the MOS are modified by addition of the substituent (each ¹ mark) a) CH=CH-CH=CH compared to CH=CH-CHO Acrolein (propenal) NET₂ NHỊCH, b) CH=CH-CN compared to CH=CH-COOH c) CH=CH-F compared to CH=CH-NH - Comparing FMO of the given compounds with each other while doing reaction with a nucleophile and electrophile a) CH=CH-CH=CH, compared to CH=CH-CHO Acrolein (propenal) b) CH=CH-CN compared to CH=CH-COOH c) CH=CH-F compared to CH=CH- NH - Predict the energetially preferred site of protonation for each of the following molecules and explain the basis of your prediction. NEL₂ (d) -NH₂
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