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Chapter 34: Problem 755

Give structural formulas for the following compounds: (a) 3-Methylindole (b) 3-Bromoquinoline (c) Nicotinic acid (d) 4-Methylisoquinoline (e) Histidine (f) 2-Methylimidazole

Short Answer

Expert verified
The structural formulas for the given compounds are: (a) 3-Methylindole: \[ \chemfig{*6(=-=(-*5(-=-=-N(-[::+60]CH_3))-))=-=)} \] (b) 3-Bromoquinoline: \[ \chemfig{*6(=-=(-*5(-=N(-[::+60]Br)---))-))=-=)} \] (c) Nicotinic acid: \[ \chemfig{*6(=-=(-N-*6(-=-=-(=[::+60]O)-[::-60]OH))-))=-=)} \] (d) 4-Methylisoquinoline: \[ \chemfig{*6(=-=(-*5(-=N(-(-[::+60]CH_3))---))-))=-=)} \] (e) Histidine: \[ \chemfig{H_2N-CH([:270]-COOH)-C(=[:+60]N(-H)-*5(-N=-(-[::+60]H)--))R} \] (f) 2-Methylimidazole: \[ \chemfig{*5(=-N-(-N*5(-=-(=[::+60]CH_3)--))-))} \]

Step by step solution

01

Identify the parent structure

Indole is an aromatic heterocyclic organic compound with a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. The molecular formula for indole is C8H7N.
02

Add the substituent

3-Methylindole is derived from indole with a methyl group at the 3rd position. So, attach a methyl group on the 3rd carbon of the indole structure.
03

Draw the structural formula

The structural formula of 3-Methylindole is: \[ \chemfig{*6(=-=(-*5(-=-=-N(-[::+60]CH_3))-))=-=)} \] (b) 3-Bromoquinoline
04

Identify the parent structure

Quinoline is an aromatic heterocyclic organic compound consisting of a fused benzene and pyridine ring. The molecular formula for quinoline is C9H7N.
05

Add the substituent

3-Bromoquinoline is derived from quinoline with a bromine atom at the 3rd position. So, attach a bromine atom on the 3rd carbon of the quinoline structure.
06

Draw the structural formula

The structural formula of 3-Bromoquinoline is: \[ \chemfig{*6(=-=(-*5(-=N(-[::+60]Br)---))-))=-=)} \] (c) Nicotinic acid
07

Identify the parent structure

Nicotinic acid is also known as pyridine-3-carboxylic acid. Pyridine is an aromatic heterocyclic organic compound with a six-membered ring containing one nitrogen atom. The molecular formula for pyridine is C5H5N.
08

Add the functional group

The carboxylic acid group (-COOH) needs to be added to the 3rd carbon of the pyridine structure.
09

Draw the structural formula

The structural formula of nicotinic acid is: \[ \chemfig{*6(=-=(-N-*6(-=-=-(=[::+60]O)-[::-60]OH))-))=-=)} \] (d) 4-Methylisoquinoline
10

Identify the parent structure

Isoquinoline is an aromatic heterocyclic organic compound, structurally similar to quinoline but with a different arrangement of the nitrogen atom. The molecular formula for isoquinoline is C9H7N.
11

Add the substituent

4-Methylisoquinoline is derived from isoquinoline with a methyl group at the 4th position. So, attach a methyl group on the 4th carbon of the isoquinoline structure.
12

Draw the structural formula

The structural formula of 4-Methylisoquinoline is: \[ \chemfig{*6(=-=(-*5(-=N(-(-[::+60]CH_3))---))-))=-=)} \] (e) Histidine
13

Identify the parent structure

Histidine is an α-amino acid, commonly found in proteins and enzymes. It is composed of a central carbon atom, an amino group (-NH2), a carboxyl group (-COOH), and an imidazole side chain.
14

Draw the structural formula

The structural formula of histidine is: \[ \chemfig{H_2N-CH([:270]-COOH)-C(=[:+60]N(-H)-*5(-N=-(-[::+60]H)--))R} \] (f) 2-Methylimidazole
15

Identify the parent structure

Imidazole is an aromatic heterocyclic organic compound, consisting of a five-membered ring with two nitrogen atoms at non-adjacent positions. The molecular formula for imidazole is C3H4N2.
16

Add the substituent

2-Methylimidazole is derived from imidazole with a methyl group at the 2nd position. So, attach a methyl group on the 2nd carbon of the imidazole structure.
17

Draw the structural formula

The structural formula of 2-Methylimidazole is: \[ \chemfig{*5(=-N-(-N*5(-=-(=[::+60]CH_3)--))-))} \]

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Most popular questions from this chapter

Mevalonic acid is the precursor of the terpenes. Write its structure. After phosphorylation, it undergoes a decarboxylative elimination to yield 3 -isopentenyl pyrophosphate. Outline the mechanism of this reaction. Where does the driving force for the reaction come from?

What are the products, and their relative ratios, resulting from the ozonolysis of \(\beta\) -carotene? (Assume reductive workup.)

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(a) Account for the aromatic properties of the imidazole ring. (b) Arrange the nitrogen atoms of histamine (the substance responsible for many allergenic reactions) in order of their expected basicity, and account for your answer.

Tropinic acid, \(\mathrm{C}_{8} \mathrm{H}_{13} \mathrm{O}_{4} \mathrm{~N}\), is a degradation product of atropine, an alkaloid of the deadly nightshade, Atropa belladonna. It has a neutralization equivalent of \(94 \pm 1 .\) It does not react with benzenesulfonyl chloride, cold dilute \(\mathrm{KMnO}_{4}\), or \(\mathrm{Br}_{2} / \mathrm{CCl}_{4} .\) Exhaustive methylation gives the following results: tropinic acid \(+\mathrm{CH}_{3} \mathrm{I} \rightarrow \mathrm{EEE}\left(\mathrm{C}_{9} \mathrm{H}_{16} \mathrm{O}_{4} \mathrm{NI}\right)\) \(\mathrm{EEE}+\mathrm{Ag}_{2} \mathrm{O}\), then strong heat \(\rightarrow \mathrm{FFF}\left(\mathrm{C}_{9} \mathrm{H}_{15} \mathrm{O}_{4} \mathrm{~N}\right)+\mathrm{H}_{2} \mathrm{O}\) \(+\mathrm{AgIFFF}+\mathrm{CH}_{3} \mathrm{I} \rightarrow \mathrm{GGG}\left(\mathrm{C}_{10} \mathrm{H}_{18} \mathrm{O}_{4} \mathrm{NI}\right)\) \(\mathrm{GGG}+\operatorname{Ag} \mathrm{O}\), then strong heat \(\rightarrow \mathrm{HHH}\left(\mathrm{C}_{7} \mathrm{H}_{8} \mathrm{O}_{4}\right)+\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}\) \(+\mathrm{H}_{2} \mathrm{O}+\mathrm{AgI}\) \(\mathrm{HHH}+\mathrm{H}_{2}, \mathrm{Ni} \rightarrow\) heptanedioic acid (pimelic acid) (a) What structures are likely for tropinic acid? (b) Tropinic acid is formed by oxidation with \(\mathrm{CrO}_{3}\) of tropinone, whose structure has been shown by synthesis to be Now what is the most likely structure for tropinic acid?
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