Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 10, Problem 10.1P
Interpretation Introduction

Interpretation: The structure of six alkenes having molecular formula C5H10 and a pair of diastereomers are to be shown.

Concept introduction: Alkenes are the compounds in which C=C double bond is present. Alkenes can be of two types: terminal alkenes and non-terminal alkenes. When double bond is present at the end of carbon chain, then it is classified as terminal alkene, whereas when double bond is present within carbon chain, then it is classified as non-terminal alkene.

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Answer to Problem 10.1P

The structure of six alkenes having molecular formula C5H10 and a pair of diastereomers are rightfully stated.

Explanation of Solution

The given molecular formula of the compound is C5H10.

The first possible structure of alkene with molecular formula C5H10 is shown below.

Organic Chemistry-Package(Custom), Chapter 10, Problem 10.1P , additional homework tip  1

Figure 1

The first possible structure of alkene contains five carbon and ten hydrogen atoms. The double bond is present between first and second carbon atom.

The second possible structure of alkene with molecular formula C5H10 is shown below.

Organic Chemistry-Package(Custom), Chapter 10, Problem 10.1P , additional homework tip  2

Figure 2

The second possible structure of alkene contains five carbon and ten hydrogen atoms. The double bond is present between first and second carbon atom. One methyl substituent is attached to the second carbon atom.

The third possible structure of alkene with molecular formula C5H10 is shown below.

Organic Chemistry-Package(Custom), Chapter 10, Problem 10.1P , additional homework tip  3

Figure 3

The third possible structure of alkene contains five carbon and ten hydrogen atoms. The double bond is present between first and second carbon atom. One methyl substituent is attached to the third carbon atom.

The fourth possible structure of alkene with molecular formula C5H10 is shown below.

Organic Chemistry-Package(Custom), Chapter 10, Problem 10.1P , additional homework tip  4

Figure 4

The fourth possible structure of alkene contains five carbon and ten hydrogen atoms. The double bond is present between second and third carbon atom. One methyl substituent is attached to the second carbon atom.

The fifth possible structure of alkene with molecular formula C5H10 is shown below.

Organic Chemistry-Package(Custom), Chapter 10, Problem 10.1P , additional homework tip  5

Figure 5

The fifth possible structure of alkene contains five carbon and ten hydrogen atoms. The double bond is present between second and third carbon atom. Substituents attached to the second and third carbon atom are on different side.

The sixth possible structure of alkene with molecular formula C5H10 is shown below.

Organic Chemistry-Package(Custom), Chapter 10, Problem 10.1P , additional homework tip  6

Figure 6

The sixth possible structure of alkene contains five carbon and ten hydrogen atoms. The double bond is present between second and third carbon atom. Substituents attached to the second and third carbon atom are on same side.

A pair of diastereomers exists when two substituents attached to each of the double bonded carbon atoms are different. The fifth and sixth structure indicates that the substituents bonded to the C=C double bond are different from each other.

Therefore, a pair of disatereomers is shown below.

Organic Chemistry-Package(Custom), Chapter 10, Problem 10.1P , additional homework tip  7

Figure 7

Conclusion

The structure of six alkenes having molecular formula C5H10 and a pair of diastereomers are rightfully stated.

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Chapter 10 Solutions

Organic Chemistry-Package(Custom)

Ch. 10 - Linolenic acidTable 10.2 and stearidonic acid are...Ch. 10 - Prob. 10.12PCh. 10 - Prob. 10.13PCh. 10 - Prob. 10.14PCh. 10 - Prob. 10.15PCh. 10 - Prob. 10.16PCh. 10 - Prob. 10.17PCh. 10 - Prob. 10.18PCh. 10 - Prob. 10.19PCh. 10 - Which compounds A-D in Figure 10.12 are formed by...Ch. 10 - What two alkenes give rise to each alcohol as the...Ch. 10 - Prob. 10.22PCh. 10 - Problem 10.23 Draw the products of each reaction,...Ch. 10 - Problem 10.24 Draw all stereoisomers formed in...Ch. 10 - Prob. 10.25PCh. 10 - Prob. 10.26PCh. 10 - Borane is sold for laboratory use as a complex...Ch. 10 - What alkylborane is formed from hydroboration of...Ch. 10 - Draw the products formed when each alkene is...Ch. 10 - What alkene can be used to prepare each alcohol as...Ch. 10 - Prob. 10.31PCh. 10 - Draw the products of each reaction using the two...Ch. 10 - Problem 10.31 Devise a synthesis of each compound...Ch. 10 - Give the IUPAC name for each compound. a.b.Ch. 10 - a Label the carbon-carbon double bond in A as E or...Ch. 10 - Prob. 10.36PCh. 10 - Calculate the number of degrees of unsaturation f...Ch. 10 - Prob. 10.38PCh. 10 - The fertility drug clomiphene trade name Clomid is...Ch. 10 - Give the IUPAC name for each compound. a....Ch. 10 - Give the structure corresponding to each name. a....Ch. 10 - 10.40 (a) Draw all possible stereoisomers of, and...Ch. 10 - Prob. 10.43PCh. 10 - 10.42 Now that you have learned how to name...Ch. 10 - Prob. 10.45PCh. 10 - Prob. 10.46PCh. 10 - Prob. 10.47PCh. 10 - Prob. 10.48PCh. 10 - By using the bond dissociation energies in...Ch. 10 - Prob. 10.50PCh. 10 - Repeat Problem 10.50 with CH32C=CH2 as the...Ch. 10 - What alkene can be used to prepare each alkyl...Ch. 10 - Prob. 10.53PCh. 10 - Draw the constitutional isomer formed in each...Ch. 10 - Prob. 10.55PCh. 10 - Draw all stereoisomers formed in each reaction....Ch. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59PCh. 10 - Draw a stepwise mechanism for the following...Ch. 10 - Draw a stepwise mechanism for each reaction. a.b.Ch. 10 - Draw a stepwise mechanism that shows how all three...Ch. 10 - Less stable alkenes can be isomerized to more...Ch. 10 - Prob. 10.64PCh. 10 - Prob. 10.65PCh. 10 - Bromoetherification, the addition of the elements...Ch. 10 - Devise a synthesis of each product from the given...Ch. 10 - Prob. 10.68PCh. 10 - Prob. 10.69PCh. 10 - Prob. 10.70PCh. 10 - 10.66 Explain why A is a stable compound but B is...Ch. 10 - Prob. 10.72PCh. 10 - Prob. 10.73PCh. 10 - 10.69 Lactones, cyclic esters such as compound A,...Ch. 10 - 10.70 Draw a stepwise mechanism for the following...Ch. 10 - 10.71 Like other electrophiles, carbocations add...Ch. 10 - 10.72 Draw a stepwise mechanism for the...
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