Diethyl malonate -

FIGURE 22.9 The synthesis of barbiturates relies on malonic ester alkylations and nucleophilic acyl substitution reactions. More than 2500 different barbiturates have been synthesized over the past 100 years.
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Diethyl malonate -

Barbital (Veronal), the first barbiturate


Diethyl malonate -

In addition to their prescribed medical uses, many barbiturates have also found widespread illegal use as street drugs. Each barbiturate often comes as a tablet of regulated size, shape, and color. Although still used today, most barbiturates have been replaced by safer, more potent alternatives with markedly different structures.


Key Terms -

```
- acetoacetic ester synthesis
- enolate ion
- \alpha-substitution reaction
- malonic ester synthesis
- decarboxylation
- tautomer
- enol
```


Key Terms -


Summary -

The $\alpha$-substitution reaction of a carbonyl compound through either an enol or enolate ion intermediate is one of the four fundamental reaction types in carbonyl-group chemistry.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0804.jpg?height=503&width=839&top_left_y=193&top_left_x=643)


Summary -

An enol
Carbonyl compounds are in an equilibrium with their enols, a process called keto-enol tautomerism. Although enol tautomers are normally present to only a small extent at equilibrium and can't usually be isolated in pure form, they nevertheless contain a highly nucleophilic double bond and react with electrophiles in an $\boldsymbol{\sigma}$-substitution reaction. An example is the $\alpha$ halogenation of ketones on treatment with $\mathrm{Cl}_{2}, \mathrm{Br}_{2}$, or $\mathrm{I}_{2}$ in acid solution. Alpha bromination of carboxylic acids can be similarly accomplished by the Hell-Volhard-Zelinskii (HVZ) reaction, in which an acid is treated with $\mathrm{Br}_{2}$ and $\mathrm{PBr}_{3}$. The $\alpha$-halogenated products can then undergo base-induced E2 elimination to yield $\alpha, \beta$-unsaturated carbonyl compounds.


Summary -

Alpha hydrogen atoms of carbonyl compounds are weakly acidic and can be removed by strong bases, such as lithium diisopropylamide (LDA), to yield nucleophilic enolate ions. The most useful reaction of enolate ions is their $\mathrm{S}_{\mathrm{N}} 2$ alkylation with alkyl halides. The Malonic ester synthesis converts an alkyl halide into a carboxylic acid with the addition of two carbon atoms ( $\mathrm{RX} \rightarrow \mathrm{RCH}_{2} \mathrm{CO}_{2} \mathrm{H}$ ). Similarly, the acetoacetic ester synthesis converts an alkyl halide into a methyl ketone with the addition of three carbon atoms (RX $\rightarrow$ $\mathrm{RCH}_{2} \mathrm{COCH}_{3}$ ). In addition, many carbonyl compounds, including ketones, esters, and nitriles, can be directly alkylated by treatment with LDA and an alkyl halide.


Summary of Reactions -


Additional Problems -


Visualizing Chemistry -

PROBLEM Show the steps in preparing each of the following substances using either a malonic ester synthesis 22-17 or an acetoacetic ester synthesis:
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0805.jpg?height=254&width=567&top_left_y=1483&top_left_x=481)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0805.jpg?height=264&width=572&top_left_y=1489&top_left_x=1118)


Visualizing Chemistry -

PROBLEM Unlike most $\beta$-diketones, the following $\beta$-diketone has no detectable enol content and is about as 22-18 acidic as acetone. Explain.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0805.jpg?height=326&width=329&top_left_y=1881&top_left_x=416)


Visualizing Chemistry -

PROBLEM For a given $\alpha$ hydrogen atom to be acidic, the $\mathrm{C}-\mathrm{H}$ bond must be parallel to the $p$ orbitals of the
22-19 $\mathrm{C}=\mathrm{O}$ double bond (that is, perpendicular to the plane of the adjacent carbonyl group). Identify the most acidic hydrogen atom in the conformation shown for the following structure. Is it axial or equatorial?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0806.jpg?height=304&width=448&top_left_y=195&top_left_x=416)


Mechanism Problems -

PROBLEM Draw the corresponding keto or enol tautomer for each of the following molecules.


Mechanism Problems -


Mechanism Problems -

PROBLEM Predict the product(s) and show the mechanism for each of the following reactions:


Mechanism Problems -

PROBLEM The following two optically active $\beta$-keto acids were decarboxylated under the conditions typically
22-23 used for the acetoacetic ester synthesis. Will the ketone products be optically active? Explain.
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0806.jpg?height=226&width=429&top_left_y=1394&top_left_x=477)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0806.jpg?height=203&width=545&top_left_y=1400&top_left_x=988)


Mechanism Problems -

PROBLEM In the Hell-Volhard-Zelinskii reaction, only a catalytic amount of $\mathrm{PBr}_{3}$ is necessary because of the
22-24 following equilibrium. Propose a mechanism for formation of the equilibrium.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0806.jpg?height=175&width=1099&top_left_y=1753&top_left_x=410)


Mechanism Problems -

PROBLEM When a ketone is treated with a halogen under acidic conditions, the $\alpha$-monohalogenated product
22-25 can be obtained in high yield. Under basic conditions however it is difficult to isolate the monohalogenated product. Explain.


Mechanism Problems -

PROBLEM Nonconjugated $\beta, \gamma$-unsaturated ketones, such as 3 -cyclohexenone, are in an acid-catalyzed
22-26 equilibrium with their conjugated $\alpha, \beta$-unsaturated isomers. Propose a mechanism for the isomerization.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0806.jpg?height=225&width=440&top_left_y=2251&top_left_x=406)


Mechanism Problems -

PROBLEM Using curved arrows, propose a mechanism for the following reaction, one of the steps in the
22-28 metabolism of the amino acid alanine.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0807.jpg?height=275&width=1001&top_left_y=600&top_left_x=410)

PROBLEM Using curved arrows, propose a mechanism for the following reaction, one of the steps in the
22-29 biosynthesis of the amino acid tyrosine.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0807.jpg?height=228&width=1048&top_left_y=1008&top_left_x=411)


Mechanism Problems -

PROBLEM One of the later steps in glucose biosynthesis is the isomerization of fructose 6-phosphate to 22-30 glucose 6-phosphate. Propose a mechanism, using acid or base catalysis as needed.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0807.jpg?height=356&width=622&top_left_y=1362&top_left_x=410)


Mechanism Problems -

Fructose 6-phosphate


Mechanism Problems -

Glucose
6-phosphate


Mechanism Problems -

PROBLEM The Favorskii reaction involves treatment of an $\alpha$-bromo ketone with base to yield a ring-contracted
22-31 product. For example, reaction of 2 -bromocyclohexanone with aqueous NaOH yields cyclopentanecarboxylic acid. Propose a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0807.jpg?height=204&width=510&top_left_y=1985&top_left_x=409)


Mechanism Problems -

PROBLEM Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion
22-32 reaction. For example, treatment of cyclohexanone with diazomethane yields cycloheptanone. Propose a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0808.jpg?height=215&width=633&top_left_y=191&top_left_x=410)


Mechanism Problems -

PROBLEM The final step in an attempted synthesis of laurene, a hydrocarbon isolated from the marine alga
22-33 Laurencia glandulifera, involved the Wittig reaction shown. The product obtained, however, was not laurene but an isomer. Propose a mechanism to account for the unexpected results.
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Laurene
(Not formed)
PROBLEM Amino acids can be prepared by reaction of alkyl halides with diethyl acetamidomalonate, followed
22-34 by heating the initial alkylation product with aqueous HCl . Show how you would prepare alanine, $\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{CO}_{2} \mathrm{H}$, one of the twenty amino acids found in proteins, and propose a mechanism for acid-catalyzed conversion of the initial alkylation product to the amino acid.
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Mechanism Problems -

Diethyl acetamidomalonate


Mechanism Problems -

PROBLEM Amino acids can also be prepared by a two-step sequence that involves Hell-Volhard-Zelinskii
22-35 reaction of a carboxylic acid followed by treatment with ammonia. Show how you would prepare leucine, $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{CO}_{2} \mathrm{H}$, and identify the mechanism of the second step.


Mechanism Problems -

PROBLEM Heating carvone with aqueous sulfuric acid converts it into carvacrol. Propose a mechanism for the 22-36 isomerization.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0808.jpg?height=261&width=738&top_left_y=1626&top_left_x=409)


Acidity of Carbonyl Compounds -


Acidity of Carbonyl Compounds -

PROBLEM Rank the following compounds in order of increasing acidity:
22-38
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$
(c) $\left(\mathrm{CH}_{3} \mathrm{CH}_{2}\right)_{2} \mathrm{NH}$
(d) $\mathrm{CH}_{3} \mathrm{COCH}_{3}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0809.jpg?height=121&width=242&top_left_y=197&top_left_x=1386)
(f) $\mathrm{CCl}_{3} \mathrm{CO}_{2} \mathrm{H}$


Acidity of Carbonyl Compounds -

PROBLEM Base treatment of the following $\alpha, \beta$-unsaturated carbonyl compound yields an anion by removal of
$\mathbf{2 2 - 4 0} \mathrm{H}^{+}$from the $\gamma$ carbon. Why are hydrogens on the $\gamma$ carbon atom acidic?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0809.jpg?height=205&width=871&top_left_y=987&top_left_x=410)


Acidity of Carbonyl Compounds -

PROBLEM Treatment of 1-phenyl-2-propenone with a strong base such as LDA does not yield an anion, even
22-41 though it contains a hydrogen on the carbon atom next to the carbonyl group. Explain.
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$\boldsymbol{\sigma}$-Substitution Reactions -

PROBLEM Predict the product(s) of the following reactions:


PROBLEM Which, if any, of the following compounds can be prepared by a malonic ester synthesis? Show the 22-43 alkyl halide you would use in each case.
(a) Ethyl pentanoate
(b) Ethyl 3-methylbutanoate
(c) Ethyl 2-methylbutanoate
(d) Ethyl 2,2-dimethylpropanoate


PROBLEM Which of the following substances would undergo the haloform reaction?
22-47
(a) $\mathrm{CH}_{3} \mathrm{COCH}_{3}$
(b) Acetophenone
(c) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHO}$
(d) $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$
(e) $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{N}$


PROBLEM How might you convert geraniol into either ethyl geranylacetate or geranylacetone?
22-48
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0810.jpg?height=410&width=1159&top_left_y=1237&top_left_x=407)