PROBLEM Aprobarbital, a barbiturate once used in treating insomnia, is synthesized in three steps from 22-49 diethyl malonate. Show how you would synthesize the necessary dialkylated intermediate, and then propose a mechanism for the reaction of this intermediate with urea to give aprobarbital.
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$\boldsymbol{\sigma}$-Substitution Reactions -

Aprobarbital


General Problems -

PROBLEM One way to determine the number of acidic hydrogens in a molecule is to treat the compound with
22-50 NaOD in $\mathrm{D}_{2} \mathrm{O}$, isolate the product, and determine its molecular weight by mass spectrometry. For example, if cyclohexanone is treated with NaOD in $\mathrm{D}_{2} \mathrm{O}$, the product has $\mathrm{MW}=102$. Explain how this method works.


General Problems -

PROBLEM When optically active ( $R$ )-2-methylcyclohexanone is treated with either aqueous base or acid, 22-51 racemization occurs. Explain.

PROBLEM Would you expect optically active ( $S$ )-3-methylcyclohexanone to be racemized on acid or base 22-52 treatment in the same way as 2-methylcyclohexanone (Problem 22-51)? Explain.


General Problems -

PROBLEM When an optically active carboxylic acid such as ( $R$ )-2-phenylpropanoic acid is brominated under 22-53 Hell-Volhard-Zelinskii conditions, is the product optically active or racemic? Explain.


General Problems -

PROBLEM Fill in the reagents a-c that are missing from the following scheme:
22-54
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0811.jpg?height=207&width=1376&top_left_y=574&top_left_x=407)


General Problems -

PROBLEM Although 2-substituted 2-cyclopentenones are in a base-catalyzed equilibrium with their
22-55 5-substituted 2-cyclopentenone isomers, the analogous isomerization is not observed for 2-substituted 2-cyclohexenones. Explain.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0811.jpg?height=205&width=576&top_left_y=941&top_left_x=411)


General Problems -


General Problems -

PROBLEM The two isomers cis- and trans-4-tert-butyl-2-methylcyclohexanone are interconverted by base 22-57 treatment. Which isomer do you think is more stable, and why?


General Problems -

PROBLEM The following synthetic routes are incorrect. What is wrong with each?
22-58 (a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0811.jpg?height=129&width=860&top_left_y=1860&top_left_x=481)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0811.jpg?height=161&width=722&top_left_y=1996&top_left_x=479)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0811.jpg?height=159&width=795&top_left_y=2165&top_left_x=478)


General Problems -

PROBLEM Attempted Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only
22-59 about $1 \%$ of the expected addition product along with $99 \%$ unreacted cyclohexanone. If $\mathrm{D}_{3} \mathrm{O}^{+}$is added to the reaction mixture after a suitable period, however, the "unreacted" cyclohexanone is found to have one deuterium atom incorporated into it. Explain.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0812.jpg?height=236&width=957&top_left_y=191&top_left_x=416)


General Problems -

PROBLEM Ketones react slowly with benzeneselenenyl chloride in the presence of HCl to yield $\alpha$-phenylseleno
22-60 ketones. Propose a mechanism for this acid-catalyzed $\alpha$-substitution reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0812.jpg?height=155&width=657&top_left_y=562&top_left_x=414)


General Problems -

PROBLEM South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue.
22-61 Chemical studies of Erythroxylon coca by Friedrich Wöhler in 1862 resulted in the discovery of cocaine, $\mathrm{C}_{17} \mathrm{H}_{21} \mathrm{NO}_{4}$, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, $\mathrm{C}_{9} \mathrm{H}_{15} \mathrm{NO}_{3}$. Oxidation of ecgonine with $\mathrm{CrO}_{3}$ yields a keto acid that readily loses $\mathrm{CO}_{2}$ on heating, giving tropinone.
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Tropinone -

(a) What is a likely structure for the keto acid?
(b) What is a likely structure for ecgonine, neglecting stereochemistry?
(c) What is a likely structure for cocaine, neglecting stereochemistry?


Tropinone -

PROBLEM The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold
22-62 Helminthosporium sativum, involves the following base treatment of a keto tosylate. What kind of reaction is occurring? How would you complete the synthesis?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0812.jpg?height=348&width=1218&top_left_y=1496&top_left_x=410)


Tropinone -

PROBLEM Sodium pentothal is a short-acting barbiturate derivative used as a general anesthetic and known 22-63 in popular culture as a truth serum. It is synthesized like other barbiturates (see the Chemistry Matters at the end of this chapter), using thiourea, $\left(\mathrm{H}_{2} \mathrm{~N}\right)_{2} \mathrm{C}=\mathrm{S}$, in place of urea. How would you synthesize sodium pentothal?
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Sodium pentothal -


CHAPTER 23 <br> Carbonyl Condensation Reactions -


FIGURE 23.1 Many of the molecules needed by all growing organisms are biosynthesized using carbonyl condensation reactions. (credit: modification of work "Newborn Sea Lion" by Steven Bedard/Flickr, CC BY 2.0)


CHAPTER CONTENTS -

23.1 Carbonyl Condensations: The Aldol Reaction
23.2 Carbonyl Condensations versus Alpha Substitutions
23.3 Dehydration of Aldol Products: Synthesis of Enones
23.4 Using Aldol Reactions in Synthesis
23.5 Mixed Aldol Reactions
23.6 Intramolecular Aldol Reactions
23.7 The Claisen Condensation Reaction
23.8 Mixed Claisen Condensations
23.9 Intramolecular Claisen Condensations: The Dieckmann Cyclization
23.10 Conjugate Carbonyl Additions: The Michael Reaction
23.11 Carbonyl Condensations with Enamines: The Stork Enamine Reaction
23.12 The Robinson Annulation Reaction
23.13 Some Biological Carbonyl Condensation Reactions


CHAPTER CONTENTS -

WHY THIS CHAPTER? We'll see later in this chapter and again in Chapter 29 that carbonyl condensation reactions occur in a large number of metabolic pathways. In fact, almost all classes of biomolecules-carbohydrates, lipids, proteins, nucleic acids, and many others-are biosynthesized through pathways that involve carbonyl condensation reactions. As with the $\alpha$-substitution reaction discussed in the previous chapter, the great value of carbonyl condensations is that they are one of the few general methods for forming carbon-carbon bonds, thereby making it possible to build larger molecules from smaller precursors. In this chapter, we'll see how and why these reactions occur.


CHAPTER CONTENTS -

We've now studied three of the four general kinds of carbonyl-group reactions and have seen two general
kinds of behavior. In nucleophilic addition and nucleophilic acyl substitution reactions, a carbonyl compound behaves as an electrophile when an electron-rich reagent adds to it. In $\alpha$-substitution reactions, however, a carbonyl compound behaves as a nucleophile when it is converted into its enol or enolate ion. In the carbonyl condensation reactions that we'll study in this chapter, the carbonyl compound behaves both as an electrophile and as a nucleophile.
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CHAPTER CONTENTS -

Electrophilic carbonyl group reacts with nucleophiles.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0814.jpg?height=175&width=213&top_left_y=449&top_left_x=1216)


CHAPTER CONTENTS -

Nucleophilic enolate ion reacts with electrophiles.


CHAPTER CONTENTS - 23.1 Carbonyl Condensations: The Aldol Reaction

Carbonyl condensation reactions take place between two carbonyl partners and involve a combination of nucleophilic addition and $\alpha$-substitution steps. One partner is converted into an enolate-ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In so doing, the nucleophilic partner undergoes an $\alpha$-substitution reaction and the electrophilic partner undergoes a nucleophilic addition. The general mechanism of the process is shown in FIGURE 23.2.