Radical Reactions -

PROBLEM Radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination
6-35 of neopentane, $\left(\mathrm{CH}_{3}\right)_{4} \mathrm{C}$, is a good way to prepare neopentyl chloride, $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{Cl}$. Explain.
PROBLEM Despite the limitations of radical chlorination of alkanes, the reaction is still useful for synthesizing
6-36 certain halogenated compounds. For which of the following compounds does radical chlorination give a single monochloro product?
(a) $\mathrm{CH}_{3} \mathrm{CH}_{3}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}$
(c)
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(d)
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(e) $\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CCH}_{3}$
(f)
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PROBLEM Draw the different monochlorinated constitutional isomers you would obtain by the radical
6-37 chlorination of the following compounds.
(a)
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(b)
<img class="imgSvg" id = "m6sn3n0ao8h87jm27qc" src="data:image/svg+xml;base64,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"/>
(c)
<img class="imgSvg" id = "m6sn3n0birhqwyha4of" src="data:image/svg+xml;base64,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"/>

PROBLEM Answer question 6-37 taking all stereoisomers into account.
6-38
PROBLEM Show the structure of the carbocation that would result when each of the following alkenes reacts 6-39 with an acid, $\mathrm{H}^{+}$.
(a)
<img class="imgSvg" id = "m6sn3n0b24brecqjiuu" src="data:image/svg+xml;base64,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"/>
(b)
<img class="imgSvg" id = "m6sn3n0ckg8m7b8xr2q" src="data:image/svg+xml;base64,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"/>
(c)
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General Problems -

PROBLEM 2-Chloro-2-methylpropane reacts with water in three steps to yield 2-methyl-2-propanol. The first
6-40 step is slower than the second, which in turn is much slower than the third. The reaction takes place slowly at room temperature, and the equilibrium constant is approximately 1.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0197.jpg?height=179&width=1481&top_left_y=187&top_left_x=422)


General Problems -

2-Chloro-2-
2-Methyl-2-propanol methylpropane
(a) Give approximate values for $\Delta G^{\ddagger}$ and $\Delta G^{\circ}$ that are consistent with the above information.
(b) Draw an energy diagram for the reaction, labeling all points of interest and placing relative energy levels on the diagram consistent with the information given.


General Problems -

PROBLEM Add curved arrows to the mechanism shown in Problem 6-40 to indicate the electron movement in
6-41 each step.
PROBLEM The reaction of hydroxide ion with chloromethane to yield methanol and chloride ion is an example
6-42 of a general reaction type called a nucleophilic substitution reaction:
$\mathrm{HO}^{-}+\mathrm{CH}_{3} \mathrm{Cl} \rightleftarrows \mathrm{CH}_{3} \mathrm{OH}+\mathrm{Cl}^{-}$
The value of $\Delta H^{\circ}$ for the reaction is $-75 \mathrm{~kJ} / \mathrm{mol}$, and the value of $\Delta S^{\circ}$ is $+54 \mathrm{~J} /(\mathrm{K} \cdot \mathrm{mol})$. What is the value of $\Delta G^{\circ}$ (in $\mathrm{kJ} / \mathrm{mol}$ ) at 298 K ? Is the reaction exothermic or endothermic? Is it exergonic or endergonic?


General Problems -

PROBLEM Methoxide ion $\left(\mathrm{CH}_{3} \mathrm{O}^{-}\right)$reacts with bromoethane in a single step according to the following
6-43 equation:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0197.jpg?height=152&width=988&top_left_y=1168&top_left_x=417)


General Problems -

Identify the bonds broken and formed, and draw curved arrows to represent the flow of electrons during the reaction.


General Problems -

PROBLEM Ammonia reacts with acetyl chloride $\left(\mathrm{CH}_{3} \mathrm{COCl}\right)$ to give acetamide $\left(\mathrm{CH}_{3} \mathrm{CONH}_{2}\right)$. Identify the bonds
6-44 broken and formed in each step of the reaction, and draw curved arrows to represent the flow of electrons in each step.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0197.jpg?height=207&width=996&top_left_y=1604&top_left_x=413)


General Problems -


General Problems -

PROBLEM The naturally occurring molecule $\alpha$-terpineol is biosynthesized by a route that includes the 6-45 following step:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0197.jpg?height=280&width=1137&top_left_y=2169&top_left_x=410)
(a) Propose a likely structure for the isomeric carbocation intermediate.
(b) Show the mechanism of each step in the biosynthetic pathway, using curved arrows to indicate electron flow.


General Problems -

PROBLEM Predict the product(s) of each of the following biological reactions by interpreting the flow of 6-46 electrons as indicated by the curved arrows:
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0198.jpg?height=255&width=502&top_left_y=401&top_left_x=481)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0198.jpg?height=256&width=430&top_left_y=403&top_left_x=1059)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0198.jpg?height=294&width=600&top_left_y=688&top_left_x=470)


General Problems -

PROBLEM Reaction of 2-methylpropene with HBr might, in principle, lead to a mixture of two alkyl bromide 6-47 addition products. Name them, and draw their structures.


General Problems -

PROBLEM Draw the structures of the two carbocation intermediates that might form during the reaction 6-48 of 2-methylpropene with HBr (Problem 6-47). We'll see in the next chapter that the stability of carbocations depends on the number of alkyl substituents attached to the positively charged carbon-the more alkyl substituents there are, the more stable the cation. Which of the two carbocation intermediates you drew is more stable?


CHAPTER 7 -


Alkenes: Structure and Reactivity -


Alkenes: Structure and Reactivity -

FIGURE 7.1 Tomatoes are good for you. Their red color is due to lycopene, which has 13 double bonds. (credit: modification of work "Tomatoes" by Jeremy Keith/Flickr, CC BY 2.0)


CHAPTER CONTENTS -

7.1 Industrial Preparation and Use of Alkenes
7.2 Calculating the Degree of Unsaturation
7.3 Naming Alkenes
7.4 Cis-Trans Isomerism in Alkenes
7.5 Alkene Stereochemistry and the $E, Z$ Designation
7.6 Stability of Alkenes
7.7 Electrophilic Addition Reactions of Alkenes
7.8 Orientation of Electrophilic Additions: Markovnikov's Rule
7.9 Carbocation Structure and Stability
7.10 The Hammond Postulate
7.11 Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements


CHAPTER CONTENTS -

WHY THIS CHAPTER? Carbon-carbon double bonds are present in most organic and biological molecules, so a good understanding of their behavior is needed. In this chapter, we'll look at some consequences of alkene stereoisomerism and then focus on the broadest and most general class of alkene reactions, the electrophilic addition reaction. Carbon-carbon triple bonds, by contrast, occur much less commonly, so we'll not spend much time on their chemistry.


CHAPTER CONTENTS -

An alkene, sometimes called an olefin from the German term for oil forming, is a hydrocarbon that contains a carbon-carbon double bond, while an alkyne is a hydrocarbon that contains a carbon-carbon triple bond. Alkenes occur abundantly in nature. Ethylene, for instance, is a plant hormone that induces ripening in fruit, and $\alpha$-pinene is the major component of turpentine. Lycopene, found in fruits such as watermelon and papaya
as well as tomatoes, is an antioxidant with numerous health benefits such as sun protection and cardiovascular protection.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0200.jpg?height=445&width=1513&top_left_y=295&top_left_x=306)


CHAPTER CONTENTS -

Lycopene, a conjugated polyene


CHAPTER CONTENTS - 7.1 Industrial Preparation and Use of Alkenes

Ethylene and propylene, the simplest alkenes, are the two most important organic chemicals produced industrially. Approximately 220 million tons of ethylene and 138 million tons of propylene are produced worldwide each year for use in the synthesis of polyethylene, polypropylene, ethylene glycol, acetic acid, acetaldehyde, and a host of other substances (FIGURE 7.2).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0200.jpg?height=1037&width=1148&top_left_y=1059&top_left_x=483)


Ethylene, propylene, and butene are synthesized from ( $\mathrm{C}_{2}-\mathrm{C}_{8}$ ) alkanes by a process called steam cracking at temperatures up to $900^{\circ} \mathrm{C}$.


$$
\begin{gathered}
\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{n} \mathrm{CH}_{3} \quad[n=0-6] \\
\downarrow \begin{array}{l}
850-900{ }^{\circ} \mathrm{C}, \\
\text { steam }
\end{array} \\
\mathrm{H}_{2}+\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}_{2}+\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}
\end{gathered}
$$


The cracking process is complex, although it undoubtedly involves radical reactions. The high-temperature
reaction conditions cause spontaneous breaking of $\mathrm{C}-\mathrm{C}$ and $\mathrm{C}-\mathrm{H}$ bonds, with the resultant formation of smaller fragments. We might imagine, for instance, that a molecule of butane splits into two ethyl radicals, each of which then loses a hydrogen atom to generate two molecules of ethylene.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0201.jpg?height=172&width=1104&top_left_y=348&top_left_x=505)


Steam cracking is an example of a reaction whose energetics are dominated by entropy ( $\Delta S^{\circ}$ ) rather than by enthalpy $\left(\Delta H^{\circ}\right)$ in the free-energy equation $\Delta G^{\circ}=\Delta H^{\circ}-T \Delta S^{\circ}$ discussed in Section 6.7. Although the bond dissociation energy $D$ for a carbon-carbon single bond is relatively high (about $370 \mathrm{~kJ} / \mathrm{mol}$ ) and cracking is endothermic, the large positive entropy change resulting from the fragmentation of one large molecule into several smaller pieces, together with the high temperature, makes the $T \Delta S^{\circ}$ term larger than the $\Delta H^{\circ}$ term, thereby favoring the cracking reaction.


CHAPTER CONTENTS - 7.2 Calculating the Degree of Unsaturation

Because of its double bond, an alkene has fewer hydrogens than an alkane with the same number of carbons $-\mathrm{C}_{n} \mathrm{H}_{2 n}$ for an alkene versus $\mathrm{C}_{n} \mathrm{H}_{2 n+2}$ for an alkane-and is therefore referred to as unsaturated. Ethylene, for example, has the formula $\mathrm{C}_{2} \mathrm{H}_{4}$, whereas ethane has the formula $\mathrm{C}_{2} \mathrm{H}_{6}$.
<img class="imgSvg" id = "m6sn3n0f1zuivqo4965" src="data:image/svg+xml;base64,PHN2ZyBpZD0ic21pbGVzLW02c24zbjBmMXp1aXZxbzQ5NjUiIHhtbG5zPSJodHRwOi8vd3d3LnczLm9yZy8yMDAwL3N2ZyIgdmlld0JveD0iMCAwIDExNSA0Mi4wMDAwMTQxMzczMDcxNzYiIHN0eWxlPSJ3aWR0aDogMTE1LjQ5OTk5OTk5OTk5NjgycHg7IGhlaWdodDogNDIuMDAwMDE0MTM3MzA3MTc2cHg7IG92ZXJmbG93OiB2aXNpYmxlOyI+PGRlZnM+PGxpbmVhckdyYWRpZW50IGlkPSJsaW5lLW02c24zbjBmMXp1aXZxbzQ5NjUtMSIgZ3JhZGllbnRVbml0cz0idXNlclNwYWNlT25Vc2UiIHgxPSI0Mi4wMDAwMDEyNzIzNTc2NSIgeTE9IjE4LjE2NTAwMDAwMDAwMDI4NyIgeDI9IjczLjUwMDAwMTI3MjM1NDQ3IiB5Mj0iMTguMTY1MDE0MTM3MzA3NDY2Ij48c3RvcCBzdG9wLWNvbG9yPSJjdXJyZW50Q29sb3IiIG9mZnNldD0iMjAlIj48L3N0b3A+PHN0b3Agc3RvcC1jb2xvcj0iY3VycmVudENvbG9yIiBvZmZzZXQ9IjEwMCUiPjwvc3RvcD48L2xpbmVhckdyYWRpZW50PjxsaW5lYXJHcmFkaWVudCBpZD0ibGluZS1tNnNuM24wZjF6dWl2cW80OTY1LTMiIGdyYWRpZW50VW5pdHM9InVzZXJTcGFjZU9uVXNlIiB4MT0iNDEuOTk5OTk4NzI3NjQyMzUiIHkxPSIyMy44MzQ5OTk5OTk5OTk3MTMiIHgyPSI3My40OTk5OTg3Mjc2MzkxOCIgeTI9IjIzLjgzNTAxNDEzNzMwNjg5MiI+PHN0b3Agc3RvcC1jb2xvcj0iY3VycmVudENvbG9yIiBvZmZzZXQ9IjIwJSI+PC9zdG9wPjxzdG9wIHN0b3AtY29sb3I9ImN1cnJlbnRDb2xvciIgb2Zmc2V0PSIxMDAlIj48L3N0b3A+PC9saW5lYXJHcmFkaWVudD48L2RlZnM+PG1hc2sgaWQ9InRleHQtbWFzay1tNnNuM24wZjF6dWl2cW80OTY1Ij48cmVjdCB4PSIwIiB5PSIwIiB3aWR0aD0iMTAwJSIgaGVpZ2h0PSIxMDAlIiBmaWxsPSJ3aGl0ZSI+PC9yZWN0PjwvbWFzaz48c3R5bGU+CiAgICAgICAgICAgICAgICAuZWxlbWVudC1tNnNuM24wZjF6dWl2cW80OTY1IHsKICAgICAgICAgICAgICAgICAgICBmb250OiAxNHB4IEhlbHZldGljYSwgQXJpYWwsIHNhbnMtc2VyaWY7CiAgICAgICAgICAgICAgICAgICAgYWxpZ25tZW50LWJhc2VsaW5lOiAnbWlkZGxlJzsKICAgICAgICAgICAgICAgIH0KICAgICAgICAgICAgICAgIC5zdWItbTZzbjNuMGYxenVpdnFvNDk2NSB7CiAgICAgICAgICAgICAgICAgICAgZm9udDogOC40cHggSGVsdmV0aWNhLCBBcmlhbCwgc2Fucy1zZXJpZjsKICAgICAgICAgICAgICAgIH0KICAgICAgICAgICAgPC9zdHlsZT48ZyBtYXNrPSJ1cmwoI3RleHQtbWFzay1tNnNuM24wZjF6dWl2cW80OTY1KSI+PGxpbmUgeDE9IjQyLjAwMDAwMTI3MjM1NzY1IiB5MT0iMTguMTY1MDAwMDAwMDAwMjg3IiB4Mj0iNzMuNTAwMDAxMjcyMzU0NDciIHkyPSIxOC4xNjUwMTQxMzczMDc0NjYiIHN0eWxlPSJzdHJva2UtbGluZWNhcDpyb3VuZDtzdHJva2UtZGFzaGFycmF5Om5vbmU7c3Ryb2tlLXdpZHRoOjEuMjYiIHN0cm9rZT0idXJsKCcjbGluZS1tNnNuM24wZjF6dWl2cW80OTY1LTEnKSI+PC9saW5lPjxsaW5lIHgxPSI0MS45OTk5OTg3Mjc2NDIzNSIgeTE9IjIzLjgzNDk5OTk5OTk5OTcxMyIgeDI9IjczLjQ5OTk5ODcyNzYzOTE4IiB5Mj0iMjMuODM1MDE0MTM3MzA2ODkyIiBzdHlsZT0ic3Ryb2tlLWxpbmVjYXA6cm91bmQ7c3Ryb2tlLWRhc2hhcnJheTpub25lO3N0cm9rZS13aWR0aDoxLjI2IiBzdHJva2U9InVybCgnI2xpbmUtbTZzbjNuMGYxenVpdnFvNDk2NS0zJykiPjwvbGluZT48L2c+PGc+PHRleHQgeD0iNzMuNDk5OTk5OTk5OTk2ODIiIHk9IjIxLjAwMDAxNDEzNzMwNzE4IiBjbGFzcz0iZGVidWciIGZpbGw9IiNmZjAwMDAiIHN0eWxlPSIKICAgICAgICAgICAgICAgIGZvbnQ6IDVweCBEcm9pZCBTYW5zLCBzYW5zLXNlcmlmOwogICAgICAgICAgICAiPjwvdGV4dD48dGV4dCB4PSI0MiIgeT0iMjEiIGNsYXNzPSJkZWJ1ZyIgZmlsbD0iI2ZmMDAwMCIgc3R5bGU9IgogICAgICAgICAgICAgICAgZm9udDogNXB4IERyb2lkIFNhbnMsIHNhbnMtc2VyaWY7CiAgICAgICAgICAgICI+PC90ZXh0PjwvZz48L3N2Zz4="/>

Ethylene: $\mathrm{C}_{2} \mathrm{H}_{4}$ (Fewer hydrogens-Unsaturated)
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Ethane: $\mathrm{C}_{2} \mathrm{H}_{6}$
(More hydrogens-Saturated)


In general, each ring or double bond in a molecule corresponds to a loss of two hydrogens from the alkane formula $\mathrm{C}_{n} \mathrm{H}_{2 n+2}$. Knowing this relationship, it's possible to work backward from a molecular formula to calculate a molecule's degree of unsaturation-the number of rings and/or multiple bonds present in the molecule.


Let's assume that we want to find the structure of an unknown hydrocarbon. A molecular weight determination yields a value of 82 amu , which corresponds to a molecular formula of $\mathrm{C}_{6} \mathrm{H}_{10}$. Since the saturated $\mathrm{C}_{6}$ alkane (hexane) has the formula $\mathrm{C}_{6} \mathrm{H}_{14}$, the unknown compound has two fewer pairs of hydrogens $\left(\mathrm{H}_{14}-\mathrm{H}_{10}=\mathrm{H}_{4}=\right.$ $2 \mathrm{H}_{2}$ ) so its degree of unsaturation is 2 . The unknown therefore contains either two double bonds, one ring and one double bond, two rings, or one triple bond. There's still a long way to go to establish its structure, but the simple calculation has told us a lot about the molecule.
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4-Methyl-1,3-pentadiene (two double bonds)
<img class="imgSvg" id = "m6sn3n0h54umd4c8i5u" 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"/>

Cyclohexene (one ring, one double bond)
<img class="imgSvg" id = "m6sn3n0ife0p2fi9qtt" 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Bicyclo[3.1.0]hexane (two rings)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0201.jpg?height=110&width=217&top_left_y=1753&top_left_x=1431)


4-Methyl-2-pentyne (one triple bond)


$$
\mathrm{C}_{6} \mathrm{H}_{10}
$$


Similar calculations can be carried out for compounds containing elements other than just carbon and hydrogen.


- Organohalogen compounds (C, H, X, where $\mathbf{X}=\mathbf{F}, \mathbf{C l}, \mathbf{B r}$, or I) A halogen substituent acts as a replacement for hydrogen in an organic molecule, so we can add the number of halogens and hydrogens to arrive at an equivalent hydrocarbon formula from which the degree of unsaturation can be found. For example, the formula $\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{Br}_{2}$ is equivalent to the hydrocarbon formula $\mathrm{C}_{4} \mathrm{H}_{8}$ and thus corresponds to one degree of unsaturation.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0202.jpg?height=256&width=757&top_left_y=181&top_left_x=711)
- Organooxygen compounds ( $\mathbf{C}, \mathbf{H}, \mathbf{0}$ ) Oxygen forms two bonds, so it doesn't affect the formula of an equivalent hydrocarbon and can be ignored when calculating the degree of unsaturation. You can convince yourself of this by seeing what happens when an oxygen atom is inserted into an alkane bond: $\mathrm{C}-\mathrm{C}$ becomes $\mathrm{C}-\mathrm{O}-\mathrm{C}$ or $\mathrm{C}-\mathrm{H}$ becomes $\mathrm{C}-\mathrm{O}-\mathrm{H}$, and there is no change in the number of hydrogen atoms. For example, the formula $\mathrm{C}_{5} \mathrm{H}_{8} \mathrm{O}$ is equivalent to the hydrocarbon formula $\mathrm{C}_{5} \mathrm{H}_{8}$ and thus corresponds to two degrees of unsaturation.


$$
\begin{aligned}
& \text { O removed from here } \\
& \mathrm{H}_{2} \mathrm{C}=\mathrm{CHCH}=\mathrm{CHCH}_{2} \mathrm{OH}=\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCH}=\mathrm{CHCH}_{2}-\mathrm{H} \\
& \mathrm{C}_{5} \mathrm{H}_{8} \mathrm{O}=\text { " } \mathrm{C}_{5} \mathrm{H}_{8} " \quad \begin{array}{l}
\text { Two unsaturations: } \\
\text { two double bonds }
\end{array}
\end{aligned}
$$


- Organonitrogen compounds ( $\mathbf{C}, \mathbf{H}, \mathbf{N}$ ) Nitrogen forms three bonds, so an organonitrogen compound has one more hydrogen than a related hydrocarbon. We therefore subtract the number of nitrogens from the number of hydrogens to arrive at the equivalent hydrocarbon formula. Again, you can convince yourself of this by seeing what happens when a nitrogen atom is inserted into an alkane bond: $\mathrm{C}-\mathrm{C}$ becomes $\mathrm{C}-\mathrm{NH}-\mathrm{C}$ or $\mathrm{C}-\mathrm{H}$ becomes $\mathrm{C}-\mathrm{NH}_{2}$, meaning that one additional hydrogen atom has been added. We must therefore subtract this extra hydrogen atom to arrive at the equivalent hydrocarbon formula. For example, the formula $\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{~N}$ is equivalent to $\mathrm{C}_{5} \mathrm{H}_{8}$ and thus has two degrees of unsaturation.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0202.jpg?height=375&width=854&top_left_y=1208&top_left_x=668)


To summarize:


- Add the number of halogens to the number of hydrogens.
- Ignore the number of oxygens.
- Subtract the number of nitrogens from the number of hydrogens.


PROBLEM Calculate the degree of unsaturation in each of the following formulas, and then draw as many
7-1 structures as you can for each:
(a) $\mathrm{C}_{4} \mathrm{H}_{8}$
(b) $\mathrm{C}_{4} \mathrm{H}_{6}$
(c) $\mathrm{C}_{3} \mathrm{H}_{4}$


PROBLEM Calculate the degree of unsaturation in each of the following formulas:
7-2 (a) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}$
(b) $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NO}_{2}$
(c) $\mathrm{C}_{8} \mathrm{H}_{9} \mathrm{Cl}_{3}$
(d) $\mathrm{C}_{9} \mathrm{H}_{16} \mathrm{Br}_{2}$
(e) $\mathrm{C}_{10} \mathrm{H}_{12} \mathrm{~N}_{2} \mathrm{O}_{3}$
(f) $\mathrm{C}_{20} \mathrm{H}_{32} \mathrm{ClN}$