Answer Key Chapter 24 - Organic Chemistry | OpenStax

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Chapter 24

N-Methylethylamine

Tricyclohexylamine

N-Ethyl-N-methylcyclohexylamine

N-Methylpyrrolidine

Diisopropylamine

1,3-Butanediamine

CH₃CH₂NH₂

NaOH

CH₃NHCH₃

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

p-Nitroaniline < p-Aminobenzaldehyde < p-Bromoaniline

p-Aminoacetophenone < p-Chloroaniline < p-Methylaniline

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

Pyrimidine is essentially 100% neutral (unprotonated).

Propanenitrile or propanamide

N-Propylpropanamide

Benzonitrile or benzamide

N-Phenylacetamide

The reaction takes place by two nucleophilic acyl substitution reactions.

Ethylamine + acetone, or isopropylamine + acetaldehyde

Aniline + acetaldehyde

Cyclopentylamine + formaldehyde, or methylamine + cyclopentanone

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

p-Methylbenzamide or p-methylbenzoyl azide

3-Octene and 4-octene

Cyclohexene

3-Heptene

Ethylene and cyclohexene

H₂C

\text{═}

CHCH₂CH₂CH₂N(CH₃)₂

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

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

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

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

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

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

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

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

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

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

4.1% protonated

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.

(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
Book URL: https://openstax.org/books/organic-chemistry/pages/1-why-this-chapter
Section URL: https://openstax.org/books/organic-chemistry/pages/chapter-24

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