General Problems -

PROBLEM Using molecular models as well as structural drawings, explain why trans-decalin is rigid and
4-52 cannot ring-flip whereas cis-decalin can easily ring-flip.
PROBLEM trans-Decalin is more stable than its cis isomer, but cis-bicyclo[4.1.0]heptane is more stable than its
4-53 trans isomer. Explain.
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trans-Decalin
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cis-Bicyclo[4.1.0]heptane


General Problems -

PROBLEM As mentioned in Problem 3-53, the statin drugs, such as simvastatin (Zocor), pravastatin (Pravachol),
4-54 and atorvastatin (Lipitor) are the most widely prescribed drugs in the world.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0125.jpg?height=641&width=1500&top_left_y=1780&top_left_x=410)
(a) Are the two indicated bonds on simvastatin cis or trans?
(b) What are the cis/trans relationships among the three indicated bonds on pravastatin?
(c) Why can't the three indicated bonds on atorvastatin be identified as cis or trans?


General Problems -


General Problems -

PROBLEM Tell whether each of the following substituents on a steroid is axial or equatorial. (A substituent that
4-58 is "up" is on the top side of the molecule as drawn, and a substituent that is "down" is on the bottom side.
(a) Substituent up at C3 (b) Substituent down at C7
(c) Substituent down at C11
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0126.jpg?height=278&width=627&top_left_y=1303&top_left_x=478)


General Problems -

Amantadine


General Problems -

PROBLEM There are two different isomers named trans-1,2-dimethylcyclopentane. Similarly, you have two
4-60 different appendages called hands. What is the relationship between them? (We'll explore this kind of isomerism in the next chapter.)
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and
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0126.jpg?height=175&width=245&top_left_y=1994&top_left_x=818)


General Problems -

PROBLEM Ketones react with alcohols to yield products called ketals. Why does the all-cis isomer of
4-61 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form a ketal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product ketal for each one.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0127.jpg?height=281&width=1015&top_left_y=174&top_left_x=398)


General Problems -

A ketal
PROBLEM Alcohols undergo an oxidation reaction to yield carbonyl compounds when treatment with $\mathrm{CrO}_{3}$.
4-62 For example, 2-tert-butylcyclohexanol gives 2-tert-butylcyclohexanone. If axial -OH groups are generally more reactive than their equatorial isomers, which do you think reacts faster, the cis isomer of 2-tert-butylcyclohexanol or the trans isomer? Explain.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0127.jpg?height=223&width=801&top_left_y=726&top_left_x=418)


CHAPTER 5 <br> Stereochemistry at Tetrahedral Centers -


FIGURE 5.1 Like the mountain whose image is reflected in a lake, many organic molecules also have mirror-image counterparts. (credit: modification of work "Crystal Lake sunrise reflection" by Sandy Horvath-Dori/Wikimedia Commons, CC BY 2.0)


CHAPTER CONTENTS -


CHAPTER CONTENTS - 5.1 Enantiomers and the Tetrahedral Carbon

5.2 The Reason for Handedness in Molecules: Chirality


CHAPTER CONTENTS - 5.3 Optical Activity

5.4 Pasteur's Discovery of Enantiomers
5.5 Sequence Rules for Specifying Configuration
5.6 Diastereomers
5.7 Meso Compounds


CHAPTER CONTENTS - 5.8 Racemic Mixtures and the Resolution of Enantiomers


CHAPTER CONTENTS - 5.9 A Review of Isomerism

5.10 Chirality at Nitrogen, Phosphorus, and Sulfur


CHAPTER CONTENTS - 5.11 Prochirality

5.12 Chirality in Nature and Chiral Environments


CHAPTER CONTENTS - 5.11 Prochirality

WHY THIS CHAPTER? Understanding the causes and consequences of molecular handedness is crucial to understanding organic and biological chemistry. The subject can be a bit complex at first, but the material covered in this chapter nevertheless forms the basis for much of the remainder of the book.


CHAPTER CONTENTS - 5.11 Prochirality

Are you right-handed or left-handed? You may not spend much time thinking about it, but handedness plays a surprisingly large role in your daily activities. Many musical instruments, such as oboes and clarinets, have a handedness to them; the last available softball glove always fits the wrong hand. The reason for these difficulties is that our hands aren't identical; rather, they're mirror images. When you hold a left hand up to a mirror, the image you see looks like a right hand. Try it.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0129.jpg?height=291&width=160&top_left_y=269&top_left_x=839)


CHAPTER CONTENTS - 5.11 Prochirality

Left hand
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0129.jpg?height=483&width=261&top_left_y=192&top_left_x=1016)


CHAPTER CONTENTS - 5.11 Prochirality

Right hand


CHAPTER CONTENTS - 5.11 Prochirality

Handedness is also important in organic and biological chemistry, where it arises primarily as a consequence of the tetrahedral stereochemistry of $s p^{3}$-hybridized carbon atoms. Many drugs and almost all the molecules in our bodies-amino acids, carbohydrates, nucleic acids, and many more-have a handedness. Furthermore, molecular handedness enables the precise interactions between enzymes and their substrates that are involved in the hundreds of thousands of chemical reactions on which life is based.


What causes molecular handedness? Look at generalized molecules of the type $\mathrm{CH}_{3} \mathrm{X}, \mathrm{CH}_{2} \mathrm{XY}$, and CHXYZ shown in FIGURE 5.2. On the left are three molecules, and on the right are their images reflected in a mirror. The $\mathrm{CH}_{3} \mathrm{X}$ and $\mathrm{CH}_{2} \mathrm{XY}$ molecules are identical to their mirror images and thus are not handed. If you make a molecular model of each molecule and its mirror image, you find that you can superimpose one on the other so that all atoms coincide. The CHXYZ molecule, by contrast, is not identical to its mirror image. You can't superimpose a model of this molecule on a model of its mirror image for the same reason that you can't superimpose a left hand on a right hand: they simply aren't the same.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0129.jpg?height=619&width=768&top_left_y=1395&top_left_x=665)


FIGURE 5.2 Tetrahedral carbon atoms and their mirror images. Molecules of the type $\mathrm{CH}_{3} \mathrm{X}$ and $\mathrm{CH}_{2} \mathrm{XY}$ are identical to their mirror images, but a molecule of the type CHXYZ is not. $\mathrm{A} C H X Y Z$ molecule is related to its mirror image in the same way a right hand is related to a left hand.


A molecule that is not identical to its mirror image is a kind of stereoisomer (Section 4.2) called an enantiomer (e-nan-tee-oh-mer, from the Greek enantio, meaning "opposite"). Enantiomers are related to each other as a right hand is related to a left hand and result whenever a tetrahedral carbon is bonded to four different substituents (one need not be H). For example, lactic acid (2-hydroxypropanoic acid) exists as a pair of enantiomers because there are four different groups ( $-\mathrm{H},-\mathrm{OH},-\mathrm{CH}_{3},-\mathrm{CO}_{2} \mathrm{H}$ ) bonded to the central carbon atom. The enantiomers are called ( + )-lactic acid and ( - )-lactic acid. Both are found in sour milk, but only the ( + ) enantiomer occurs in muscle tissue.
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Lactic acid: a molecule of the general formula CHXYZ -


No matter how hard you try, you can't superimpose a molecule of (+)-lactic acid on a molecule of (-)-lactic acid. If any two groups match up, say -H and $-\mathrm{CO}_{2} \mathrm{H}$, the remaining two groups don't match (FIGURE 5.3).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0130.jpg?height=242&width=695&top_left_y=936&top_left_x=401)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0130.jpg?height=220&width=570&top_left_y=947&top_left_x=1146)

FIGURE 5.3 Attempts at superimposing the mirror-image forms of lactic acid. (a) When the -H and -OH substituents match up, the $-\mathrm{CO}_{2} \mathrm{H}$ and $-\mathrm{CH}_{3}$ substituents don't; (b) when $-\mathrm{CO}_{2} \mathrm{H}$ and $-\mathrm{CH}_{3}$ match up, -H and -OH don't. Regardless of how the molecules are oriented, they aren't identical.


Lactic acid: a molecule of the general formula CHXYZ - 5.2 The Reason for Handedness in Molecules: Chirality

A molecule that is not identical to its mirror image is said to be chiral (ky-ral, from the Greek cheir, meaning "hand"). You can't take a chiral molecule and its enantiomer and place one on the other so that all atoms coincide.


How can you predict whether a given molecule is or is not chiral? A molecule is not chiral if it has a plane of symmetry. A plane of symmetry is a plane that cuts through the middle of a molecule (or any object) in such a way that one half of the molecule or object is a mirror image of the other half. A coffee mug, for example, has a plane of symmetry. If you were to cut the coffee mug in half from top to bottom, one half would be a mirror image of the other half. A hand, however, does not have a plane of symmetry. One "half" of a hand is not a mirror image of the other half (FIGURE 5.4).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0130.jpg?height=503&width=570&top_left_y=1792&top_left_x=775)


FIGURE 5.4 The meaning of symmetry plane. (a) An object like the coffee mug has a symmetry plane cutting through it so that right and left halves are mirror images. (b) An object like a hand has no symmetry plane; the right "half" of a hand is not a mirror image of the left half.


A molecule that has a plane of symmetry in any conformation must be identical to its mirror image and must be nonchiral, or achiral. Thus, propanoic acid, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$, has a plane of symmetry when lined up as shown in FIGURE 5.5 and is achiral, while lactic acid, $\mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{CO}_{2} \mathrm{H}$, has no plane of symmetry in any conformation
and is chiral.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0131.jpg?height=646&width=242&top_left_y=260&top_left_x=508)
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FIGURE 5.5 The achiral propanoic acid molecule versus the chiral lactic acid molecule. Propanoic acid has a plane of symmetry that makes one side of the molecule a mirror image of the other. Lactic acid has no such symmetry plane.


The most common, although not the only, cause of chirality in organic molecules is the presence of a tetrahedral carbon atom bonded to four different groups-for example, the central carbon atom in lactic acid. Such carbons are referred to as chirality centers, although other terms such as stereocenter, asymmetric center, and stereogenic center have also been used. Note that chirality is a property of the entire molecule, whereas a chirality center is the cause of chirality.


Detecting a chirality center in a complex molecule takes practice because it's not always immediately apparent whether four different groups are bonded to a given carbon. The differences don't necessarily appear right next to the chirality center. For example, 5 -bromodecane is a chiral molecule because four different groups are bonded to C 5 , the chirality center (marked with an asterisk). A butyl substituent is similar to a pentyl substituent, but it isn't identical. The difference isn't apparent until looking four carbon atoms away from the chirality center, but there's still a difference.
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As other possible examples, look at methylcyclohexane and 2-methylcyclohexanone. Methylcyclohexane is achiral because no carbon atom in the molecule is bonded to four different groups. You can immediately eliminate all $-\mathrm{CH}_{2}$ - carbons and the $-\mathrm{CH}_{3}$ carbon from consideration, but what about C 1 on the ring? The C 1 carbon atom is bonded to $\mathrm{a}-\mathrm{CH}_{3}$ group, to an -H atom, and to C 2 and C 6 of the ring. Carbons 2 and 6 are equivalent, however, as are carbons 3 and 5 . Thus, the C6-C5-C4 "substituent" is equivalent to the C2-C3-C4 substituent, and methylcyclohexane is achiral. Another way of reaching the same conclusion is to realize that methylcyclohexane has a symmetry plane, which passes through the methyl group and through C1 and C4 of the ring.

The situation is different for 2-methylcyclohexanone. 2-Methylcyclohexanone has no symmetry plane and is chiral because its C 2 is bonded to four different groups: $-\mathrm{CH}_{3}$ group, an -H atom, $\mathrm{a}-\mathrm{COCH}_{2}-$ ring bond (C1), and a $-\mathrm{CH}_{2} \mathrm{CH}_{2}-$ ring bond (C3).
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