Visualizing Chemistry -

PROBLEM The enamine prepared from acetone and dimethylamine is shown in its lowest-energy form.
19-29 (a) What is the geometry and hybridization of the nitrogen atom?
(b) What orbital on nitrogen holds the lone pair of electrons?
(c) What is the geometric relationship between the $p$ orbitals of the double bond and the nitrogen orbital that holds the lone pair? Why do you think this geometry represents the minimum energy?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0685.jpg?height=340&width=345&top_left_y=1315&top_left_x=478)


Mechanism Problems -


Mechanism Problems -

PROBLEM Predict the product(s) and propose a mechanism for each of the following reactions:
19-31 (a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0685.jpg?height=123&width=730&top_left_y=2020&top_left_x=481)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0685.jpg?height=186&width=651&top_left_y=2162&top_left_x=482)

PROBLEM Predict the product(s) and propose a mechanism for each of the following reactions:
19-32
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0686.jpg?height=202&width=1299&top_left_y=189&top_left_x=413)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0686.jpg?height=144&width=600&top_left_y=199&top_left_x=437)
b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0686.jpg?height=164&width=590&top_left_y=219&top_left_x=1109)

PROBLEM Predict the product(s) and propose a mechanism for each of the following reactions:
19-33 (a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0686.jpg?height=112&width=633&top_left_y=470&top_left_x=486)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0686.jpg?height=201&width=665&top_left_y=599&top_left_x=481)

PROBLEM Predict the product(s) and propose mechanisms for the following reactions:


Mechanism Problems -

PROBLEM The following reaction begins with an acetal and converts it into a different acetal. Predict the
19-35 product(s) and propose a mechanism.
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0686.jpg?height=153&width=727&top_left_y=1230&top_left_x=485)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0686.jpg?height=108&width=768&top_left_y=1399&top_left_x=486)


Mechanism Problems -

PROBLEM When $\alpha$-glucose is treated with an acid catalyst in the presence of an alcohol, an acetal is formed.
19-36 Propose a mechanism for this process and give the structure of the stereoisomeric acetal that you would also expect as a product.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0686.jpg?height=237&width=906&top_left_y=1687&top_left_x=417)


Mechanism Problems -

PROBLEM Predict the products of the following Wolff-Kishner reactions. Write the mechanism for each,
19-37 beginning from the hydrazone intermediate.
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0686.jpg?height=201&width=448&top_left_y=2049&top_left_x=481)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0686.jpg?height=203&width=402&top_left_y=2048&top_left_x=1005)


Mechanism Problems -

PROBLEM Aldehydes can be prepared by the Wittig reaction using (methoxymethylene)triphenylphosphorane 19-38 as the Wittig reagent and then hydrolyzing the product with acid. For example,
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0687.jpg?height=286&width=1078&top_left_y=185&top_left_x=404)
(a) How would you prepare the necessary phosphorane?
(b) Propose a mechanism for the hydrolysis step.


Mechanism Problems -

PROBLEM One of the steps in the metabolism of fats is the reaction of an unsaturated acyl CoA with water to 19-39 give a $\beta$-hydroxyacyl CoA. Propose a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0687.jpg?height=104&width=838&top_left_y=685&top_left_x=416)


Mechanism Problems -

Unsaturated acyl CoA
$\beta$-Hydroxyacyl CoA
PROBLEM Aldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield 19-40 acetals. Predict the product of the following reaction, and propose a mechanism:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0687.jpg?height=171&width=647&top_left_y=977&top_left_x=411)


Mechanism Problems -

PROBLEM Ketones react with dimethylsulfonium methylide to yield epoxides. Suggest a mechanism for the
19-41 reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0687.jpg?height=302&width=898&top_left_y=1269&top_left_x=402)


Mechanism Problems -

PROBLEM Propose a mechanism for the following reaction.
19-42
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0687.jpg?height=223&width=814&top_left_y=1645&top_left_x=406)


Mechanism Problems -

PROBLEM Paraldehyde, a sedative and hypnotic agent, is prepared by treatment of acetaldehyde with an acidic
19-43 catalyst. Propose a mechanism for the reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0687.jpg?height=245&width=625&top_left_y=1989&top_left_x=403)


Paraldehyde -

PROBLEM The Meerwein-Ponndorf-Verley reaction involves reduction of a ketone by treatment with an
19-44 excess of aluminum triisopropoxide, $\left[\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHO}\right]_{3} \mathrm{Al}$. The mechanism of the process is closely related to the Cannizzaro reaction in that a hydride ion acts as a leaving group. Propose a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0688.jpg?height=199&width=781&top_left_y=188&top_left_x=409)


Paraldehyde -

PROBLEM Propose a mechanism to account for the formation of 3,5-dimethylpyrazole from hydrazine and
19-45 2,4-pentanedione. What has happened to each carbonyl carbon in going from starting material to product.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0688.jpg?height=286&width=684&top_left_y=556&top_left_x=420)


Paraldehyde -


Paraldehyde -

PROBLEM Trans alkenes are converted into their cis isomers and vice versa on epoxidation followed by 19-47 treatment of the epoxide with triphenylphosphine. Propose a mechanism for the reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0688.jpg?height=133&width=1064&top_left_y=1343&top_left_x=414)


Paraldehyde -

PROBLEM Treatment of an $\alpha, \beta$-unsaturated ketone with basic aqueous hydrogen peroxide yields an epoxy
19-48 ketone. The reaction is specific to unsaturated ketones; isolated alkene double bonds do not react. Propose a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0688.jpg?height=158&width=565&top_left_y=1664&top_left_x=417)


Paraldehyde -

PROBLEM One of the biological pathways by which an amine is converted to a ketone involves two steps: (1)
19-49 oxidation of the amine by $\mathrm{NAD}^{+}$to give an imine and (2) hydrolysis of the imine to give a ketone plus ammonia. Glutamate, for instance, is converted by this process into $\alpha$-ketoglutarate. Show the structure of the imine intermediate, and propose mechanisms for both steps.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0688.jpg?height=199&width=1188&top_left_y=2053&top_left_x=414)


Paraldehyde -

PROBLEM Primary amines react with esters to yield amides: $\mathrm{RCO}_{2} \mathrm{R}^{\prime}+\mathrm{R}^{\prime \prime} \mathrm{NH}_{2} \rightarrow \mathrm{RCONHR}{ }^{\prime \prime}+\mathrm{R}^{\prime} \mathrm{OH}$. Propose a 19-50 mechanism for the following reaction of an $\alpha, \beta$-unsaturated ester.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0689.jpg?height=248&width=1056&top_left_y=188&top_left_x=407)


Paraldehyde -

PROBLEM When crystals of pure $\alpha$-glucose are dissolved in water, isomerization occurs slowly to produce 19-51 $\beta$-glucose. Propose a mechanism for the isomerization.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0689.jpg?height=245&width=777&top_left_y=563&top_left_x=411)


Paraldehyde -

PROBLEM The Wharton reaction converts an epoxy ketone to an allylic alcohol by reaction with hydrazine.
19-52 Review the Wolff-Kishner reaction in Section 19.9 and then propose a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0689.jpg?height=212&width=1091&top_left_y=935&top_left_x=411)


Paraldehyde -

Naming Aldehydes and Ketones
PROBLEM Draw structures corresponding to the following names:
19-53
(a) Bromoacetone
(b) (S)-2-Hydroxypropanal
(c) 2-Methyl-3-heptanone
(d) $(2 S, 3 R)-2,3,4$-Trihydroxybutanal (e) 2,2,4,4-Tetramethyl-3-pentanone
(f) 4-Methyl-3-penten-2-one (g) Butanedial (h) 3-Phenyl-2-propenal
(i) 6,6-Dimethyl-2,4-cyclohexadienone (j) p-Nitroacetophenone


Paraldehyde -

PROBLEM Draw and name the seven aldehydes and ketones with the formula $\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}$. Which are chiral? 19-54


Paraldehyde -

PROBLEM Draw structures of compounds that fit the following descriptions:
19-56 (a) An $\alpha, \beta$-unsaturated ketone, $\mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}$
(b) An $\alpha$-diketone (c) An aromatic ketone, $\mathrm{C}_{9} \mathrm{H}_{10} \mathrm{O}$
(d) A diene aldehyde, $\mathrm{C}_{7} \mathrm{H}_{8} \mathrm{O}$


Paraldehyde -

Reactions of Aldehydes and Ketones
PROBLEM Predict the products of the reaction of (1) phenylacetaldehyde and (2) acetophenone with the
19-57 following reagents:
(a) $\mathrm{NaBH}_{4}$, then $\mathrm{H}_{3} \mathrm{O}^{+}$
(b) Dess-Martin reagent
(c) $\mathrm{NH}_{2} \mathrm{OH}, \mathrm{HCl}$ catalyst
(d) $\mathrm{CH}_{3} \mathrm{MgBr}$, then $\mathrm{H}_{3} \mathrm{O}^{+}$
(e) $2 \mathrm{CH}_{3} \mathrm{OH}, \mathrm{HCl}$ catalyst (f) $\mathrm{H}_{2} \mathrm{NNH}_{2}, \mathrm{KOH}$
(g) $\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{P}=\mathrm{CH}_{2}$
(h) $\mathrm{HCN}, \mathrm{KCN}$


Paraldehyde -

PROBLEM How would you use a Grignard reaction on an aldehyde or ketone to synthesize the following 19-59 compounds?
(a) 2-Pentanol
(b) 1-Butanol
(c) 1-Phenylcyclohexanol
(d) Diphenylmethanol


Paraldehyde -

PROBLEM How might you carry out the following selective transformations? One of the two schemes requires
19-60 a protection step. (Recall from Section 19.4 that aldehydes are more reactive than ketones toward nucleophilic addition.)
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0690.jpg?height=117&width=738&top_left_y=836&top_left_x=479)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0690.jpg?height=112&width=708&top_left_y=963&top_left_x=481)


Paraldehyde -

Carvone
(a) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{Cu}^{-} \mathrm{Li}^{+}$, then $\mathrm{H}_{3} \mathrm{O}^{+}$
(b) $\mathrm{LiAlH}_{4}$, then $\mathrm{H}_{3} \mathrm{O}^{+}$
(c) $\mathrm{CH}_{3} \mathrm{NH}_{2}$
(d) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{MgBr}$, then $\mathrm{H}_{3} \mathrm{O}^{+}$
(e) $\mathrm{H}_{2} / \mathrm{Pd}$
(f) $\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{OH}, \mathrm{HCl}$
(g) $\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \stackrel{+-}{\mathrm{P}} \mathrm{HCH}_{3}$


Paraldehyde -

PROBLEM How would you synthesize the following compounds from cyclohexanone?
19-64 (a) 1-Methylcyclohexene (b) 2-Phenylcyclohexanone (c) cis-1,2-Cyclohexanediol
(d) 1-Cyclohexylcyclohexanol


Spectroscopy -

PROBLEM At what position would you expect to observe IR absorptions for the following molecules?


19-65 (a) -


19-65 (a) -

PROBLEM Acid-catalyzed dehydration of 3-hydroxy-3-phenylcyclohexanone leads to an unsaturated ketone.
19-66 What possible structures are there for the product? At what position in the IR spectrum would you expect each to absorb? If the actual product has an absorption at $1670 \mathrm{~cm}^{-1}$, what is its structure?


19-65 (a) -

PROBLEM Propose structures for molecules that meet the following descriptions. Assume that the kinds of 19-68 carbons ( $1^{\circ}, 2^{\circ}, 3^{\circ}$, or $4^{\circ}$ ) have been assigned by DEPT-NMR.
(a) $\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}$; IR: $1715 \mathrm{~cm}^{-1}$; ${ }^{13} \mathrm{C}$ NMR: $8.0 \delta\left(1^{\circ}\right)$, $18.5 \delta\left(1^{\circ}\right), 33.5 \delta\left(2^{\circ}\right), 40.6 \delta\left(3^{\circ}\right), 214.0 \delta\left(4^{\circ}\right)$
(b) $\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}$; IR: $1730 \mathrm{~cm}^{-1}$; ${ }^{13} \mathrm{C}$ NMR: $22.6 \delta\left(1^{\circ}\right), 23.6 \delta\left(3^{\circ}\right), 52.8 \delta\left(2^{\circ}\right), 202.4 \delta\left(3^{\circ}\right)$
(c) $\mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}$; IR: $1680 \mathrm{~cm}^{-1}$; ${ }^{13} \mathrm{C}$ NMR: $22.9 \delta\left(2^{\circ}\right), 25.8 \delta\left(2^{\circ}\right), 38.2 \delta\left(2^{\circ}\right), 129.8 \delta\left(3^{\circ}\right), 150.6 \delta\left(3^{\circ}\right)$, 198.7 ( $4^{\circ}$ )


19-65 (a) -

PROBLEM Compound $\mathbf{A}, \mathrm{C}_{8} \mathrm{H}_{10} \mathrm{O}_{2}$, has an intense IR absorption at $1750 \mathrm{~cm}^{-1}$ and gives the ${ }^{13} \mathrm{C}$ NMR spectrum 19-69 shown. Propose a structure for A.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0692.jpg?height=502&width=1391&top_left_y=191&top_left_x=413)


19-65 (a) -

PROBLEM Propose structures for ketones or aldehydes that have the following ${ }^{1} \mathrm{H}$ NMR spectra:
19-70 (a) $\mathrm{C}_{4} \mathrm{H}_{7} \mathrm{ClO}$
IR: $1715 \mathrm{~cm}^{-1}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0692.jpg?height=505&width=1402&top_left_y=883&top_left_x=475)
(b) $\mathrm{C}_{7} \mathrm{H}_{14} \mathrm{O}$


19-65 (a) -

IR: $1710 \mathrm{~cm}^{-1}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0692.jpg?height=502&width=1408&top_left_y=1516&top_left_x=472)


General Problems -

PROBLEM When 4-hydroxybutanal is treated with methanol in the presence of an acid catalyst, 19-71 2-methoxytetrahydrofuran is formed. Explain.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0692.jpg?height=106&width=665&top_left_y=2213&top_left_x=416)


General Problems -

PROBLEM The $\mathrm{S}_{\mathrm{N}} 2$ reaction of (dibromomethyl)benzene, $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHBr}_{2}$, with NaOH yields benzaldehyde rather 19-72 than (dihydroxymethyl)benzene, $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}(\mathrm{OH})_{2}$. Explain.


General Problems -

PROBLEM Reaction of 2-butanone with HCN yields a chiral product. What stereochemistry does the product 19-73 have? Is it optically active?


General Problems -

PROBLEM The amino acid methionine is biosynthesized by a multistep route that includes reaction of an 19-74 imine of pyridoxal phosphate (PLP) to give an unsaturated imine, which then reacts with cysteine. What kinds of reactions are occurring in the two steps?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0693.jpg?height=362&width=1167&top_left_y=451&top_left_x=433)


O-SuccinylhomoserinePLP imine <br> Unsaturated imine -

PROBLEM Each of the following reaction schemes has one or more flaws. What is wrong in each case? How 19-75 would you correct each scheme?
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0693.jpg?height=201&width=1176&top_left_y=1011&top_left_x=480)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0693.jpg?height=107&width=1242&top_left_y=1215&top_left_x=482)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0693.jpg?height=179&width=888&top_left_y=1320&top_left_x=415)


PROBLEM Tamoxifen is a drug used in the treatment of breast cancer. How would you prepare tamoxifen from 19-77 benzene, the following ketone, and any other reagents needed?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0693.jpg?height=437&width=1059&top_left_y=1858&top_left_x=411)


PROBLEM Compound $\mathbf{A}, \mathrm{MW}=86$, shows an IR absorption at $1730 \mathrm{~cm}^{-1}$ and a very simple ${ }^{1} \mathrm{H}$ NMR spectrum 19-78 with peaks at $9.7 \delta(1 \mathrm{H}$, singlet) and $1.2 \delta(9 \mathrm{H}$, singlet). Propose a structure for A.
PROBLEM Compound $\mathbf{B}$ is isomeric with $\mathbf{A}$ (Problem 19-78) and shows an IR peak at $1715 \mathrm{~cm}^{-1}$. The ${ }^{1} \mathrm{H}$ NMR 19-79 spectrum of $\mathbf{B}$ has peaks at $2.4 \delta(1 \mathrm{H}$, septet, $J=7 \mathrm{~Hz}), 2.1 \delta(3 \mathrm{H}$, singlet), and $1.2 \delta(6 \mathrm{H}$, doublet, $J$
$=7 \mathrm{~Hz})$. What is the structure of $\mathbf{B}$ ?
PROBLEM The ${ }^{1} \mathrm{H}$ NMR spectrum shown is that of a compound with the formula $\mathrm{C}_{9} \mathrm{H}_{10} \mathrm{O}$. How many double 19-80 bonds and/or rings does this compound contain? If the unknown compound has an IR absorption at $1690 \mathrm{~cm}^{-1}$, what is a likely structure?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0694.jpg?height=500&width=1394&top_left_y=409&top_left_x=420)

PROBLEM The ${ }^{1} \mathrm{H}$ NMR spectrum shown is that of a compound isomeric with the one in Problem 19-80. This 19-81 isomer has an IR absorption at $1730 \mathrm{~cm}^{-1}$. Propose a structure. [Note: Aldehyde protons (CHO) often show low coupling constants to adjacent hydrogens, so the splitting of aldehyde signals is not always apparent.]
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0694.jpg?height=497&width=1395&top_left_y=1128&top_left_x=422)


PROBLEM Propose structures for ketones or aldehydes that have the following ${ }^{1} \mathrm{H}$ NMR spectra:
19-82 (a) $\mathrm{C}_{9} \mathrm{H}_{10} \mathrm{O}_{2}$ : IR: $1695 \mathrm{~cm}^{-1}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0694.jpg?height=497&width=1399&top_left_y=1757&top_left_x=477)
(b) $\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}:$ IR: $1690 \mathrm{~cm}^{-1}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0695.jpg?height=503&width=1394&top_left_y=258&top_left_x=477)

PROBLEM Propose structures for ketones or aldehydes that have the following ${ }^{1} \mathrm{H}$ NMR spectra.
19-83 (a) $\mathrm{C}_{10} \mathrm{H}_{12} \mathrm{O}$ : IR: $1710 \mathrm{~cm}^{-1}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0695.jpg?height=510&width=1397&top_left_y=886&top_left_x=472)
(b) $\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}_{3}$ : IR: $1715 \mathrm{~cm}^{-1}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0695.jpg?height=503&width=1405&top_left_y=1467&top_left_x=471)


PROBLEM When glucose (Problem 19-51) is treated with $\mathrm{NaBH}_{4}$, reaction occurs to yield sorbitol, a 19-84 polyalcohol commonly used as a food additive. Show how this reduction occurs.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0695.jpg?height=177&width=822&top_left_y=2107&top_left_x=413)


Glucose
Sorbitol


PROBLEM The proton and carbon NMR spectra for each of three isomeric ketones with the formula $\mathrm{C}_{7} \mathrm{H}_{14} \mathrm{O}$ are
19-85 shown. Assign a structure to each pair of spectra.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0696.jpg?height=2218&width=1500&top_left_y=181&top_left_x=410)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0697.jpg?height=2110&width=1492&top_left_y=192&top_left_x=411)


PROBLEM The proton NMR spectrum for a compound with formula $\mathrm{C}_{10} \mathrm{H}_{12} \mathrm{O}_{2}$ is shown below. The infrared 19-86 spectrum has a strong band at $1711 \mathrm{~cm}^{-1}$. The broadband-decoupled 13C NMR spectral results are tabulated along with the DEPT-135 and DEPT-90 information. Draw the structure of this compound.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0698.jpg?height=689&width=1489&top_left_y=192&top_left_x=416)


CHAPTER 20 -

Carboxylic Acids and Nitriles
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0699.jpg?height=915&width=1890&top_left_y=342&top_left_x=231)


CHAPTER 20 -

FIGURE 20.1 The burning sensation produced by touching or eating chili peppers is due to capsaicin, a carboxylic acid derivative called an amide. (credit: modification of "Chillis" by Lucas Cobb/Flickr, CC BY 2.0)


CHAPTER CONTENTS -

20.1 Naming Carboxylic Acids and Nitriles
20.2 Structure and Properties of Carboxylic Acids
20.3 Biological Acids and the Henderson-Hasselbalch Equation
20.4 Substituent Effects on Acidity
20.5 Preparing Carboxylic Acids
20.6 Reactions of Carboxylic Acids: An Overview
20.7 Chemistry of Nitriles
20.8 Spectroscopy of Carboxylic Acids and Nitriles


CHAPTER CONTENTS -

WHY THIS CHAPTER? Carboxylic acids are present in many industrial processes and most biological pathways and are the starting materials from which other acyl derivatives are made. Thus, an understanding of their properties and reactions is fundamental to understanding organic chemistry. We'll look both at acids and at their close relatives, nitriles ( $\mathrm{RC} \equiv \mathrm{N}$ ), in this chapter and at carboxylic acid derivatives in the next chapter.


CHAPTER CONTENTS -

Carboxylic acids, $\mathbf{R C O}_{\mathbf{2}} \mathbf{H}$, occupy a central place among carbonyl compounds. Not only are they valuable in themselves, they also serve as starting materials for preparing numerous carboxylic acid derivatives such as acid chlorides, esters, amides, and thioesters. In addition, carboxylic acids are present in the majority of biological pathways.
<img class="imgSvg" id = "m6sn3oso0xcgajzdq9s" 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An acid chloride $\quad$ An ester


CHAPTER CONTENTS -

A great many carboxylic acids are found in nature: acetic acid, $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$, is the chief organic component of vinegar; butanoic acid, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$, is responsible for the rancid odor of sour butter; and hexanoic acid (caproic acid), $\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CO}_{2} \mathrm{H}$, is responsible for the unmistakable aroma of goats and dirty gym socks (the name comes from the Latin caper, meaning "goat"). Other examples are cholic acid, a major component of human bile, and long-chain aliphatic acids such as palmitic acid, $\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{14} \mathrm{CO}_{2} \mathrm{H}$, a biological precursor of fats and vegetable oils.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0700.jpg?height=345&width=598&top_left_y=982&top_left_x=411)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0700.jpg?height=364&width=652&top_left_y=975&top_left_x=1043)


CHAPTER CONTENTS -

Cholic acid
Approximately 20 million tons of acetic acid is produced worldwide each year for a variety of purposes, including preparation of the vinyl acetate polymer used in paints and adhesives. About $20 \%$ of the acetic acid synthesized industrially is obtained by oxidation of acetaldehyde. Much of the remaining $80 \%$ is prepared by the rhodium-catalyzed reaction of methanol with carbon monoxide.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0700.jpg?height=136&width=654&top_left_y=1580&top_left_x=733)


CHAPTER CONTENTS - 20.1 Naming Carboxylic Acids and Nitriles


Carboxylic Acids, $\mathrm{RCO}_{2} \mathrm{H}$ -

Simple carboxylic acids derived from open-chain alkanes are systematically named by replacing the terminal $-e$ of the corresponding alkane name with -oic acid. The $-\mathrm{CO}_{2} \mathrm{H}$ carbon atom is numbered C 1 .
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Propanoic acid
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4-Methylpentanoic acid
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3-Ethyl-6-methyloctanedioic acid


Compounds that have $\mathrm{a}-\mathrm{CO}_{2} \mathrm{H}$ group bonded to a ring are named using the suffix -carboxylic acid. The $\mathrm{CO}_{2} \mathrm{H}$ carbon is attached to C 1 in this system and is not itself numbered. As a substituent, the $\mathrm{CO}_{2} \mathrm{H}$ group is called a carboxyl group.
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trans-4-Hydroxycyclohexanecarboxylic acid
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1-Cyclopentenecarboxylic acid


Because many carboxylic acids were among the first organic compounds to be isolated and purified, quite a few common names exist (TABLE 20.1). Biological chemists, in particular, make frequent use of these names, so you may find yourself referring back to this list on occasion. We'll use systematic names in this book, with a few exceptions such as formic (methanoic) acid and acetic (ethanoic) acid, whose names are accepted by IUPAC and are so well known that it makes little sense to refer to them any other way.
Also listed in TABLE 20.1 are the names of acyl groups $\binom{\mathrm{O}}{\mathrm{R}-\mathrm{C}-}$ derived from the parent acids. Except for the eight entries at the top of TABLE 20.1, whose names have a -yl ending, all other acyl groups are named using an -oyl ending.

TABLE 20.1 Common Names of Some Carboxylic Acids and Acyl Groups


| Structure | Name | Acyl group |
| :---: | :---: | :---: |
| $\mathrm{HCO}_{2} \mathrm{H}$ | Formic | Formyl |
| $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$ | Acetic | Acetyl |
| $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$ | Propionic | Propionyl |
| $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$ | Butyric | Butyryl |
| $\mathrm{HO}_{2} \mathrm{CCO}_{2} \mathrm{H}$ | Oxalic | Oxalyl |
| $\mathrm{HO}_{2} \mathrm{CCH}_{2} \mathrm{CO}_{2} \mathrm{H}$ | Malonic | Malonyl |
| $\mathrm{HO}_{2} \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$ | Succinic | Succinyl |
| $\mathrm{HO}_{2} \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$ | Glutaric | Glutaryl |
| $\mathrm{HO}_{2} \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$ | Adipic | Adipoyl |
| $\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCO}_{2} \mathrm{H}$ | Acrylic | Acryloyl |
| $\mathrm{HO}_{2} \mathrm{CCH}=\mathrm{CHCO}_{2} \mathrm{H}$ | Maleic (cis) Fumaric (trans) | Maleoyl Fumaroyl |
| $\mathrm{HOCH}_{2} \mathrm{CO}_{2} \mathrm{H}$ | Glycolic | Glycoloyl |
| <smiles>CC(O)C(=O)O</smiles> | Lactic | Lactoyl |
| <smiles>CC(=O)O</smiles> | Pyruvic | Pyruvoyl |
| <smiles>O=C(O)C(O)CO</smiles> | Glyceric | Glyceroyl |


TABLE 20.1 Common Names of Some Carboxylic Acids and Acyl Groups


| Structure | Name | Acyl group |
| :---: | :---: | :---: |
| <smiles>O=C(O)CC(O)C(=O)O</smiles> | Malic | Maloyl |
| <smiles>O=C(O)CC(=O)O</smiles> | Oxaloacetic | Oxaloacetyl |
| <smiles>O=C(O)c1ccccc1</smiles> | Benzoic | Benzoyl |
| <smiles>O=C(O)c1ccccc1C(=O)O</smiles> | Phthalic | Phthaloyl |


Nitriles, $\mathrm{RC} \equiv \mathrm{N}$ -

Compounds containing the $-\mathrm{C} \equiv \mathrm{N}$ functional group are called nitriles and can undergo some chemistry similar to that of carboxylic acids. Simple open-chain nitriles are named by adding -nitrile as a suffix to the alkane name, with the nitrile carbon numbered C 1 .


$$
\underset{5}{\mathrm{CH}_{3}} \stackrel{\mathrm{C}_{4}^{\mathrm{CH}} \mathrm{CH}_{3}}{\mathrm{CH}_{3}}
$$


Nitriles can also be named as derivatives of carboxylic acids by replacing the -ic acid or -oic acid ending with -onitrile, or by replacing the -carboxylic acid ending with -carbonitrile. The nitrile carbon atom is attached to C 1 but is not itself numbered.


$$
\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{~N}
$$


Acetonitrile (from acetic acid)
 Benzonitrile
 (from benzoic acid) -

2,2-Dimethylcyclohexanecarbonitrile (from 2,2-dimethylcyclohexanecarboxylic acid)


Methyl 4-cyanopentanoate -


Methyl 4-cyanopentanoate -

PROBLEM Draw structures corresponding to the following IUPAC names:
20-2 (a) 2,3-Dimethylhexanoic acid (b) 4-Methylpentanoic acid
(c) trans-1,2-Cyclobutanedicarboxylic acid (d) o-Hydroxybenzoic acid
(e) (9Z,12Z)-9,12-Octadecadienoic acid (f) 2-Pentenenitrile


Methyl 4-cyanopentanoate - 20.2 Structure and Properties of Carboxylic Acids

Carboxylic acids are similar in some respects to both ketones and alcohols. Like ketones, the carboxyl carbon is $s p^{2}$-hybridized, and carboxylic acid groups are therefore planar with $\mathrm{C}-\mathrm{C}=\mathrm{O}$ and $\mathrm{O}=\mathrm{C}-\mathrm{O}$ bond angles of approximately $120^{\circ}$ (TABLE 20.2).


| TABLE 20.2 Physical Parameters for Acetic Acid |  |  |  |  |
| :--- | :--- | :--- | :--- | :---: |
|  |  |  |  |  |
|  |  |  |  |  |
| Bond angle | (degrees) | Bond length | (pm) |  |
| $\mathrm{C}-\mathrm{C}=\mathrm{O}$ | 119 | $\mathrm{C}-\mathrm{C}$ | 152 |  |
| $\mathrm{C}-\mathrm{C}-\mathrm{OH}$ | 119 | $\mathrm{C}=\mathrm{O}$ | 125 |  |
| $\mathrm{O}=\mathrm{C}-\mathrm{OH}$ | 122 | $\mathrm{C}-\mathrm{OH}$ | 131 |  |


Like alcohols, carboxylic acids are strongly associated because of hydrogen-bonding. Most carboxylic acids exist as cyclic dimers held together by two hydrogen bonds. This strong hydrogen-bonding has a noticeable effect on boiling points, making carboxylic acids boil far less easily than their corresponding alcohols. Acetic acid, for instance, has a boiling point of $117.9^{\circ} \mathrm{C}$, versus $78.3^{\circ} \mathrm{C}$ for ethanol, even though both compounds have two carbons.


Acetic acid dimer
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0703.jpg?height=320&width=698&top_left_y=1543&top_left_x=918)


The most obvious property of carboxylic acids is implied by their name: carboxylic acids are acidic. They therefore react with bases such as NaOH and $\mathrm{NaHCO}_{3}$ to give metal carboxylate salts, $\mathrm{RCO}_{2}{ }^{-} \mathrm{M}^{+}$. Carboxylic acids with more than six carbons are only slightly soluble in water, but the alkali metal salts of carboxylic acids are often highly water-soluble. In fact, it's often possible to purify an acid by extracting its salt into aqueous base, then reacidifying and extracting the pure acid back into an organic solvent.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0703.jpg?height=232&width=877&top_left_y=2123&top_left_x=624)


Like other Brønsted-Lowry acids discussed in Section 2.7, carboxylic acids dissociate slightly in dilute aqueous solution to give $\mathrm{H}_{3} \mathrm{O}^{+}$and the corresponding carboxylate anions, $\mathrm{RCO}_{2}{ }^{-}$. The extent of dissociation is given by an acidity constant, $K_{\mathrm{a}}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0704.jpg?height=288&width=752&top_left_y=184&top_left_x=681)


A list of $K_{\mathrm{a}}$ values for various carboxylic acids is given in TABLE 20.3. For most, $K_{\mathrm{a}}$ is approximately $10^{-4}$ to $10^{-5}$. Acetic acid, for instance, has $K_{\mathrm{a}}=1.75 \times 10^{-5}$ at $25^{\circ} \mathrm{C}$, which corresponds to a $\mathrm{p} K_{\mathrm{a}}$ of 4.76 . In practical terms, a $K_{\mathrm{a}}$ value near $10^{-5}$ means that only about $0.1 \%$ of the molecules in a 0.1 M solution are dissociated, as opposed to the $100 \%$ dissociation found with strong mineral acids like HCl .