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Chapter 11: Problem 60

Write structural formulas for these compounds: (a) trans-2-pentene, (b) 2-ethyl-1-butene, (c) 4 -ethyltrans-2-heptene, (d) 3 -phenyl- 1 -butyne.

Short Answer

Expert verified
This exercise demonstrates understanding the IUPAC (International Union of Pure and Applied Chemistry) nomenclature for organic compounds and drawing their structural formulas. Each part of the compound's name provides information about its structure. In trans-2-pentene, there are 5 carbons with a double bond at carbon 2. In 2-ethyl-1-butene, there's a double bond at carbon 1 and an ethyl group at carbon 2. For 4-ethyltrans-2-heptene, there's a double bond at carbon 2 and an ethyl group at carbon 4. Lastly, in 3-phenyl-1-butyne, a phenyl group is attached at carbon 3 with a triple bond at carbon 1.

Step by step solution

01

Draw the structure for trans-2-pentene

The prefix 'pent' indicates a 5-carbon main chain. 'ene' suggests the presence of a carbon-carbon double bond, which is located at carbon 2 as suggested by the '2-' prefix. 'trans-' means opposite side of the double bond but in this case there are no substituents, only hydrogen atoms. Thus the structure would be CH3-CH=CH-CH2-CH3 with the double bond between the second and third carbons and hydrogens opposite one another.
02

Draw the structure for 2-ethyl-1-butene

'but' indicates a 4-carbon main chain with a double bond at carbon 1. '2-ethyl' means there is an ethyl (2 carbon) substituent coming off of carbon 2. Hence the structure is CH2=CH-CH(CH2-CH3)-CH3. In this molecule, the double bond is at carbon 1 and an ethyl group is present at carbon 2.
03

Draw the structure for 4-ethyltrans-2-heptene

'hept' indicates a 7-carbon main chain and 'ene' represents a double bond at the second carbon atom. '4-ethyl' indicates an ethyl substituent at the 4th carbon atom. 'trans' means the substituents (2 ethyl groups) occur on opposite sides of the double bond. Hence, the structure is CH3-CH=CH-CH(CH2-CH3)-CH2-CH2-CH3. In this structure, the double bond is at carbon 2 and the ethyl group is on carbon 4.
04

Draw the structure for 3-phenyl-1-butyne

'but' suggests a 4-carbon main chain. 'yne' represents a triple bond at carbon 1. '3-phenyl' indicates a phenyl ring at carbon 3. Therefore, the structure is CH≡C-CH2-C6H5. In this structure, the triple bond is at carbon 1 and the phenyl group is at carbon 3.

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Most popular questions from this chapter

Which of these amino acids are chiral: (a) \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\) (b) \(\mathrm{CH}_{2}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\) (c) \(\mathrm{CH}_{2}(\mathrm{OH}) \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH} ?\)

Give examples of a chiral substituted alkane and an achiral substituted alkane.

2-Butanone can be reduced to 2 -butanol by reagents such as lithium aluminum hydride \(\left(\mathrm{LiAlH}_{4}\right)\). (a) Write the formula of the product. Is it chiral? (b) In reality, the product does not exhibit optical activity. Explain.

Name the classes to which these compounds belong: (a) \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{OC}_{2} \mathrm{H}_{5}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{CHO}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\) (e) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\)

Complete this equation and identify the products: $$\mathrm{HCOOH}+\mathrm{CH}_{3} \mathrm{OH} \longrightarrow$$
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