UV Spectroscopy -

Pyridine
PROBLEM Would you expect allene, $\mathrm{H}_{2} \mathrm{C}=\mathrm{C}=\mathrm{CH}_{2}$, to show a UV absorption in the 200 to 400 nm range?
14-46 Explain.
PROBLEM The following ultraviolet absorption maxima have been measured:
14-47


UV Spectroscopy -

| 1,3-Butadiene | 217 nm |
| :--- | :--- |
| 2-Methyl-1,3-butadiene | 220 nm |
| 1,3-Pentadiene | 223 nm |
| 2,3-Dimethyl-1,3-butadiene | 226 nm |
| 2,4-Hexadiene | 227 nm |
| 2,4-Dimethyl-1,3-pentadiene | 232 nm |
| 2,5-Dimethyl-2,4-hexadiene | 240 nm |


UV Spectroscopy -

What conclusion can you draw about the effect of alkyl substitution on UV absorption maxima? Approximately what effect does each added alkyl group have?


UV Spectroscopy -

PROBLEM 1,3,5-Hexatriene has $\lambda_{\max }=258 \mathrm{~nm}$. In light of your answer to Problem 14-47, approximately
14-48 where would you expect 2,3-dimethyl-1,3,5-hexatriene to absorb?
PROBLEM $\beta$-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the
14-49 molecular formula $\mathrm{C}_{10} \mathrm{H}_{16}$ and a UV absorption maximum at 232 nm . On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of $\beta$-ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments:
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UV Spectroscopy -


General Problems -


General Problems -

PROBLEM Answer the following questions for 1,3,5-cycloheptatriene.
14-51 (a) How many $p$ atomic orbitals are in the conjugated system?
(b) How many molecular orbitals describe the conjugated system?
(c) How many molecular orbitals are bonding molecular orbitals?
(d) How many molecular orbitals are anti-bonding molecular orbitals?
(e) Which molecular orbitals are filled with electrons?
(f) If this molecule were to absorb a photon of UV light an electron would move between which two molecular orbitals (be specific)?


General Problems -

PROBLEM Treatment of 3,4-dibromohexane with strong base leads to loss of 2 equivalents of HBr and
14-52 formation of a product with formula $\mathrm{C}_{6} \mathrm{H}_{10}$. Three products are possible. Name each of the three, and tell how you would use ${ }^{1} \mathrm{H}$ and ${ }^{13} \mathrm{C}$ NMR spectroscopy to help identify them. How would you use UV spectroscopy?


General Problems -

PROBLEM Addition of HCl to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclohexane as a sole product.
14-53 Use resonance structures to explain why none of the other regioisomer is formed.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0476.jpg?height=169&width=557&top_left_y=1198&top_left_x=410)


General Problems -

PROBLEM Aldrin, a chlorinated insecticide now banned from use in most countries since 1990, can be made
14-54 by Diels-Alder reaction of hexachloro-1,3-cyclopentadiene with norbornadiene. What is the structure of aldrin?
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Norbornadiene -

PROBLEM Norbornadiene (Problem 14-54) can be prepared by reaction of chloroethylene with
14-55 1,3-cyclopentadiene, followed by treatment of the product with sodium ethoxide. Write the overall scheme, and identify the two kinds of reactions.


Norbornadiene -

PROBLEM The triene shown here reacts with 2 equivalents of maleic anhydride to yield a product with the
14-56 formula $\mathrm{C}_{17} \mathrm{H}_{16} \mathrm{O}_{6}$. Predict a structure for the product.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0476.jpg?height=245&width=760&top_left_y=2013&top_left_x=411)


Norbornadiene -

PROBLEM Myrcene, $\mathrm{C}_{10} \mathrm{H}_{16}$, is found in oil of bay leaves and is isomeric with $\beta$-ocimene (Problem 14-49).
14-57 It has an ultraviolet absorption at 226 nm and can be hydrogenated to yield 2,6-dimethyloctane. On ozonolysis followed by zinc/acetic acid treatment, myrcene yields formaldehyde, acetone, and 2-oxopentanedial:
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Norbornadiene -

2-Oxopentanedial
Propose a structure for myrcene, and write the reactions, showing starting material and products.


Norbornadiene -

PROBLEM Hydrocarbon $\mathbf{A}, \mathrm{C}_{10} \mathrm{H}_{14}$, has a UV absorption at $\lambda_{\max }=236 \mathrm{~nm}$ and gives hydrocarbon $\mathbf{B}, \mathrm{C}_{10} \mathrm{H}_{18}$, on
14-58 hydrogenation. Ozonolysis of $\mathbf{A}$, followed by zinc/acetic acid treatment, yields the following diketo dialdehyde:
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Norbornadiene -

An illustration shows the structure of diketo dialdehyde. It shows two carbonyl groups single bonded to each other. Each carbonyl group is bonded to a chain of three methylene groups and then to an aldehyde group.
(a) Propose two possible structures for $\mathbf{A}$.
(b) Hydrocarbon $\mathbf{A}$ reacts with maleic anhydride to yield a Diels-Alder adduct. Which of your structures for A is correct?
(c) Write the reactions, showing the starting material and products.


Norbornadiene -

PROBLEM Adiponitrile, a starting material used in the manufacture of nylon, can be prepared in three steps
14-59 from 1,3-butadiene. How would you carry out this synthesis?
$\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCH}=\mathrm{CH}_{2} \quad \xrightarrow{3 \text { steps }} \mathrm{N} \equiv \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{N}$
Adiponitrile
PROBLEM Ergosterol, a precursor of vitamin D, has $\lambda_{\max }=282 \mathrm{~nm}$ and molar absorptivity $\epsilon=11,900$. What is
14-60 the concentration of ergosterol in a solution whose absorbance $A=0.065$ with a sample pathlength $l=1.00 \mathrm{~cm}$ ?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0477.jpg?height=356&width=980&top_left_y=1383&top_left_x=410)


Norbornadiene -


Norbornadiene -

Dimethyl butynedioate
PROBLEM Dimethyl butynedioate also undergoes a Diels-Alder reaction with (2E,4Z)-2,4-hexadiene, but the
14-62 stereochemistry of the product is different from that of the ( $2 E, 4 E$ ) isomer (Problem 14-61). Explain.


Norbornadiene -

PROBLEM How would you carry out the following synthesis (more than one step is required)? What
14-63 stereochemical relationship between the $-\mathrm{CO}_{2} \mathrm{CH}_{3}$ group attached to the cyclohexane ring and the -CHO groups would your synthesis produce?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0478.jpg?height=264&width=820&top_left_y=182&top_left_x=406)


Norbornadiene -

PROBLEM The double bond of an enamine (alkene + amine) is much more nucleophilic than a typical alkene
14-64 double bond. Assuming that the nitrogen atom in an enamine is $s p^{2}$-hybridized, draw an orbital picture of an enamine, and explain why the double bond is electron-rich.
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An enamine -


CHAPTER 15 -

Benzene and Aromaticity
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0479.jpg?height=1036&width=1888&top_left_y=352&top_left_x=235)


CHAPTER 15 -

FIGURE 15.1 A fennel plant is an aromatic herb used in cooking. A phenyl group-pronounced exactly the same way-is the characteristic structural unit of "aromatic" organic compounds. (credit: modificatio of work "Fennel" by Ruth Hartnup/Flickr, CC BY 2.0)


CHAPTER CONTENTS -


CHAPTER CONTENTS - 15.1 Naming Aromatic Compounds

15.2 Structure and Stability of Benzene
15.3 Aromaticity and the Hückel $4 n+2$ Rule
15.4 Aromatic Ions
15.5 Aromatic Heterocycles: Pyridine and Pyrrole
15.6 Polycyclic Aromatic Compounds
15.7 Spectroscopy of Aromatic Compounds


WHY THIS CHAPTER? The reactivity of substituted aromatic compounds, more than that of any other class of substances, is intimately tied to their exact structure. As a result, aromatic compounds provide an extraordinarily sensitive probe for studying the relationship between structure and reactivity. We'll examine this relationship here and in the following chapter, and we'll find that the lessons learned are applicable to all other organic compounds, including important substances such as the nucleic acids that control our genetic makeup.


In the early days of organic chemistry, the word aromatic was used to describe such fragrant substances as benzaldehyde (from cherries, peaches, and almonds), toluene (from Tolu balsam), and benzene (from coal distillate). It was soon realized, however, that substances grouped as aromatic differed from most other organic compounds in their chemical behavior.
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Benzene
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Benzaldehyde
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Toluene