Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 3.SE, Problem 54AP
In the next chapter we'll look at cycloalkanes—saturated cyclic hydrocarbons—and we’ll see that the molecules generally adopt puckered, nonplanar conformations. Cyclohexane, for instance, has a puckered shape like a lounge chair rather than a flat shape. Why?
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Chemistry
2.) Draw the condensed structures (NOT line structures) for the following reactions of
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CH3
a.)
H3C-
[H']
CH2-CH-
CH3
CH3
H3C-CH-CH3
b.) H;C-CH2-CH-CH2 CH2-OH
[0]
What is the relationship of these two structures?
You are teaching a class in organic chemistry to grade 12 students. Outline the differences in 3 physical properties between alkanes, alcohols, and
carboxylic acids. Note: they all have the same hydrocarbon length.
Chapter 3 Solutions
Organic Chemistry
Ch. 3.1 - Prob. 1PCh. 3.1 - Prob. 2PCh. 3.1 - Identify the functional groups in the following...Ch. 3.2 - Draw structures of the five isomers of C6H14.Ch. 3.2 - Propose structures that meet the following...Ch. 3.2 - Prob. 6PCh. 3.3 - Draw the eight 5-carbon alkyl groups (pentyl...Ch. 3.3 - Identify the carbon atoms in the following...Ch. 3.3 - Prob. 9PCh. 3.3 - Prob. 10P
Ch. 3.4 - Give IUPAC names for the following compounds:Ch. 3.4 - Prob. 12PCh. 3.4 - Name the eight 5-carbon alkyl groups you drew in...Ch. 3.4 - Give the IUPAC name for the following hydrocarbon,...Ch. 3.7 - Make a graph of potential energy versus angle of...Ch. 3.7 - Sight along the C2-C1 bond of 2-methylpropane...Ch. 3.7 - Sight along the C2-C3 bond of 2,3-dimethylbutane,...Ch. 3.7 - Draw a Newman projection along the C2-C3 bond of...Ch. 3.SE - Prob. 19VCCh. 3.SE - Prob. 20VCCh. 3.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 3.SE - Prob. 22APCh. 3.SE - Prob. 23APCh. 3.SE - Propose structures for the following: (a) A...Ch. 3.SE - Prob. 25APCh. 3.SE - Draw the structures of the following molecules:...Ch. 3.SE - Draw structures that meet the following...Ch. 3.SE - Prob. 28APCh. 3.SE - In each of the following sets, which structures...Ch. 3.SE - There are seven constitutional isomers with the...Ch. 3.SE - Prob. 31APCh. 3.SE - Draw compounds that contain the following: (a) A...Ch. 3.SE - Prob. 33APCh. 3.SE - Draw and name all monochloro derivatives of...Ch. 3.SE - Draw structures for the following: (a)...Ch. 3.SE - Prob. 36APCh. 3.SE - Draw a compound that: (a) Has nine primary...Ch. 3.SE - Give IUPAC names for the following compounds:Ch. 3.SE - Name the five isomers of C6H14.Ch. 3.SE - Explain why each of the following names is...Ch. 3.SE - Prob. 41APCh. 3.SE - Consider 2-methylbutane (isopentane). Sighting...Ch. 3.SE - What are the relative energies of the three...Ch. 3.SE - Construct a qualitative potential-energy diagram...Ch. 3.SE - Prob. 45APCh. 3.SE - Draw the most stable conformation of pentane,...Ch. 3.SE - Draw the most stable conformation of...Ch. 3.SE - Prob. 48APCh. 3.SE - Prob. 49APCh. 3.SE - Formaldehyde, H2C=O, is known to all biologists...Ch. 3.SE - Prob. 51APCh. 3.SE - Increased substitution around a bond leads to...Ch. 3.SE - Prob. 53APCh. 3.SE - In the next chapter we'll look at...Ch. 3.SE - We’ll see in the next chapter that there are two...
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- Distinguish between isomerism and resonance. Distinguish between structural and geometric isomerism. When writing the various structural isomers, the most difficult task is identifying which are different isomers and which are identical to a previously written structurethat is, which are compounds that differ only by the rotation of a carbon single bond. How do you distinguish between structural isomers and those that are identical? Alkenes and cycloalkanes are structural isomers of each other. Give an example of each using C4H8. Another common feature of alkenes and cycloalkanes is that both have restricted rotation about one or more bonds in the compound, so both can exhibit cis- trans isomerism. What is required for an alkene or cycloalkane to exhibit cis-trans isomerism? Explain the difference between cis and trans isomers. Alcohols and ethers are structural isomers of each other, as are aldehydes and ketones. Give an example of each to illustrate. Which functional group in Table 21-4 can be structural isomers of carboxylic acids? What is optical isomerism? What do you look for to determine whether an organic compound exhibits optical isomerism? 1-Bromo-1-chloroethane is optically active whereas 1-bromo-2-chloroethane is not optically active. Explain.arrow_forward1,3-dimethylcyclohexane and Cl2 forms what?arrow_forwardnon 10 Which C5H12 isomer will have the highest boiling point?arrow_forward
- 1 12. Identify the set of compounds that have the same functional group. (a) C2H6, C2H4, C2H2 (b) C2H2, CH3COOH, CH3CONH2 (с) СНЗСН2CНО, Н2СО, СНЗСH2CH2CH2CНO (d) CH3NH2, CH3CH2CONH2, CH3CH2CONHCH3 (e) СНЗС(О)СНз, СНЗСООН, CH:CH2CHOarrow_forwardFatty acids are molecules with a carboxylic acid on one end and long hydrocarbon chain on the other. The sodium salts of fatty acids (such as sodium strearate, shown below) are commonly used in soaps to trap nonpolar dirt and grease particles. Soap does not work well in "hard water, which is water with high concentration of magensium and calcium ions (often found in water obtained from wells) Explain this observation at a molecular level.arrow_forwardWould there 5 isomers for hydrocarbons with the formula C4H8 ? ( including stereoisomersarrow_forward
- Why do alkanes, alkenes, and alkynes have a relatively low boiling point? O They have no large intermolecular forces holding them together. O They have no diple moments or polarity. O They have a lot of electron density in a very small amout of space.arrow_forwardFor the following, you must draw an appropriate structure that has the chemical formula C5H7O2Cl with the indicated functional group(s) and/or property. In each case, identify any other functional groups in the molecule you draw, that were not indicated in the question. You may use Lewis or bond- line structures to draw your molecules. You may not use the same structure to answer more than 1 question. a) An acyclic molecule that cannot form hydrogen bonds with itself b) A tertiary chloride c) A cyclic etherarrow_forwardDraw Lewis structures and condensed structural formulas for the four alcohols with the molecular formula C4H10O. Classify each alcohol as primary, secondary, or tertiary. (Hint: First consider the connectivity of the four carbon atoms; they can be bonded either four in a chain or three in a chain with the fourth carbon as a branch on the middle carbon. Then consider the points at which the iOH group can be bonded to each carbon chain.)arrow_forward
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