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Organic Chemistry

Chapter 24

Organic ChemistryChapter 24

(a)

N-Methylethylamine

(b)

Tricyclohexylamine

(c)

N-Ethyl-N-methylcyclohexylamine

(d)

N-Methylpyrrolidine

(e)

Diisopropylamine

(f)

1,3-Butanediamine

(a)

(b)

(c)

The structure of N-methylaniline. It comprises a benzene ring with an N H group linked to a methyl group.

(d)

The structure of N-ethyl-N-methylcyclopentylamine. It comprises nitrogen with ethyl, methyl, and cyclopentyl substituents.

(e)

The structure of N-isopropylcyclohexylamine. It comprises cyclohexane linked to an N H linked to a C H group further connected to two methyl groups at C 1.

(f)

A five-membered ring, one member of which is nitrogen. There are double bonds at C 2 and C 4, and nitrogen has an additional ethyl substituent.

(a)

A benzene ring fused to another five-membered ring, one member of which is nitrogen. There is a double bond between non-fusion carbon atoms. Benzene has a methoxy substituent.

(b)

A five-membered ring, one member of which is nitrogen. There are double bonds at C 2 and C 4, methyl at C 3, and nitrogen has an additional methyl substituent.

(c)

A six-membered ring, one member of which is nitrogen, with alternating single and double bonds. Opposite the nitrogen is the substituent N with two methyl groups.

(d)

A six-membered ring, two members of which are nitrogen, with one carbon between them. There are alternating single and double bonds. C 5 has an amino substituent.

(a)

CH₃CH₂NH₂

(b)

NaOH

(c)

CH₃NHCH₃

Propylamine is stronger; benzylamine pK_b = 4.67; propylamine pK_b = 3.29

(a)

p-Nitroaniline < p-Aminobenzaldehyde < p-Bromoaniline

(b)

p-Aminoacetophenone < p-Chloroaniline < p-Methylaniline

(c)

p-(Trifluoromethyl)aniline < p-(Fluoromethyl)aniline < p-Methylaniline

Pyrimidine is essentially 100% neutral (unprotonated).

(a)

Propanenitrile or propanamide

(b)

N-Propylpropanamide

(c)

Benzonitrile or benzamide

(d)

N-Phenylacetamide

The reaction takes place by two nucleophilic acyl substitution reactions.

4-(2-Bromoethyl)benzene-1,2-diol reacts with ammonia or 4-(bromomethyl)benzene-1,2-diol reacts with sodium cyanide, then lithium aluminum hydride.

(a)

Ethylamine + acetone, or isopropylamine + acetaldehyde

(b)

Aniline + acetaldehyde

(c)

Cyclopentylamine + formaldehyde, or methylamine + cyclopentanone

A benzene ring with aldehyde group on C 1 and methyl on C 3 reacts with dimethylamine in the presence of sodium borohydride. The product is not mentioned.

(a)

4,4-Dimethylpentanamide or 4,4-dimethylpentanoyl azide

(b)

p-Methylbenzamide or p-methylbenzoyl azide

(a)

3-Octene and 4-octene

(b)

Cyclohexene

(c)

3-Heptene

(d)

Ethylene and cyclohexene

H₂C

\text{═}

CHCH₂CH₂CH₂N(CH₃)₂

1. HNO₃, H₂SO₄; 2. H₂/PtO₂; 3. (CH₃CO)₂O; 4. HOSO₂Cl; 5. aminothiazole; 6. H₂O, NaOH

(a)

1. HNO₃, H₂SO₄; 2. H₂/PtO₂; 3. 2 CH₃Br

(b)

1. HNO₃, H₂SO₄; 2. H₂/PtO₂; 3. (CH₃CO)₂O; 4. Cl₂; 5. H₂O, NaOH

(c)

1. HNO₃, H₂SO₄; 2. Cl₂, FeCl₃; 3. SnCl₂

(d)

1. HNO₃, H₂SO₄; 2. H₂/PtO₂; 3. (CH₃CO)₂O; 4. 2 CH₃Cl, AlCl₃; 5. H₂O, NaOH

(a)

1. CH₃Cl, AlCl₃; 2. HNO₃, H₂SO₄; 3. SnCl₂; 4. NaNO₂, H₂SO₄; 5. CuBr; 6. KMnO₄, H₂O

(b)

1. HNO₃, H₂SO₄; 2. Br₂, FeBr₃; 3. SnCl₂, H₃O⁺; 4. NaNO₂, H₂SO₄; 5. CuCN; 6. H₃O⁺

(c)

1. HNO₃, H₂SO₄; 2. Cl₂, FeCl₃; 3. SnCl₂; 4. NaNO₂, H₂SO₄; 5. CuBr

(d)

1. CH₃Cl, AlCl₃; 2. HNO₃, H₂SO₄; 3. SnCl₂; 4. NaNO₂, H₂SO₄; 5. CuCN; 6. H₃O⁺

(e)

1. HNO₃, H₂SO₄; 2. H₂/PtO₂; 3. (CH₃CO)₂O; 4. 2 Br₂; 5. H₂O, NaOH; 6. NaNO₂, H₂SO₄; 7. CuBr

1. HNO₃, H₂SO₄; 2. SnCl₂; 3a. 2 equiv. CH₃I; 3b. NaNO₂, H₂SO₄; 4. product of 3a + product of 3b

Orbital diagram of thiazole involving nitrogen, sulfur, and three hydrogens, all s p 2 hybridized. N and S carry lone pairs of electrons; six total electrons in the pi system.

4.1% protonated

The attack of electrophile at C 2, C 3, and C 4 of pyridine. Mechanisms showing attack at C 2 and C 4 are labeled unfavorable.

The side-chain nitrogen is more basic than the ring nitrogen.

Reaction at C2 is disfavored because the aromaticity of the benzene ring is lost.

Structure of indole with arrows showing C 3 attacking electrophile. Resulting resonance structures show loss of aromaticity due to 8 electrons in pi system.

(CH₃)₃CCOCH₃ → (CH₃)₃CCH(NH₂)CH₃

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- Authors: John McMurry, Professor Emeritus
- Publisher/website: OpenStax
- Book title: Organic Chemistry
- Publication date: Sep 20, 2023
- Location: Houston, Texas
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- Section URL: https://openstax.org/books/organic-chemistry/pages/chapter-24

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