Question 18 An analogue of the local anaesthetic lidocaine (2) can be synthesised in two st below. weaker base Amine. primary MeHNH₂C a) Then MeHNH C Step 1 Step 2 € CH, CH, CH, CH₂ NH₂ CH₂CI ل · tertiary CH₂CI H amine CH₂CH₂ CH ₂ CH ₁ MeHNHC. MAHNH C CH, CH₂ сн, сн.

Organic Chemistry
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Author:John E. McMurry
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Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
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Problem 38MP: Benzenediazonium carboxylate decomposes when heated to yield N2, CO2, and a reactive substance that...
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Question 18
An analogue of the local anaesthetic lidocaine (2) can be synthesised in two steps as shown
below.
weaker base
primary
MeHNH C
MeHNH ₂C
Step 1
A mine.
Qoi
NH₂
Step 2
(1)
CH,
CH₂
CH,
CH₂
· tertiary
CH₂CI
b) Draw the reaction mechanism for step 2
amine
H
CH₂CH3
4₂ CH 3
MeHNH C
MeHNH C
CH,
CH,
amide
CH₂
CH₂CH₂
2CH₂
・Secondary
(2)
a) These reactions involve four different types of nitrogen which have been circled above.
Accurately name the four types of nitrogen. Rank these in terms of base strength and
explain their differences in basicity.
secondary> primary> tertiary
Quaternary > tertiary) Secondary primary.
Transcribed Image Text:Question 18 An analogue of the local anaesthetic lidocaine (2) can be synthesised in two steps as shown below. weaker base primary MeHNH C MeHNH ₂C Step 1 A mine. Qoi NH₂ Step 2 (1) CH, CH₂ CH, CH₂ · tertiary CH₂CI b) Draw the reaction mechanism for step 2 amine H CH₂CH3 4₂ CH 3 MeHNH C MeHNH C CH, CH, amide CH₂ CH₂CH₂ 2CH₂ ・Secondary (2) a) These reactions involve four different types of nitrogen which have been circled above. Accurately name the four types of nitrogen. Rank these in terms of base strength and explain their differences in basicity. secondary> primary> tertiary Quaternary > tertiary) Secondary primary.
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