Chemistry for Today: General  Organic  and Biochemistry
Chemistry for Today: General Organic and Biochemistry
9th Edition
ISBN: 9781337514576
Author: Seager
Publisher: Cengage
Question
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Chapter 12, Problem 12.27E
Interpretation Introduction

(a)

Interpretation:

The structural formula for the alkene with molecular formula C5H10 that gives 2, 3-dibromopentane as the product is to be stated.

Concept introduction:

The addition reactions are defined as the formation of one product by the combination of two or more products. For example, in halogenation, the addition of a halogen molecule results in the reduction of carbon-carbon double bond to carbon-carbon single bond and formation of haloalkane.

Expert Solution
Check Mark

Answer to Problem 12.27E

The structural formula for the alkene with molecular formula C5H10 that gives 2, 3-dibromopentane as product is CH3CH2CH=CHCH3.

Explanation of Solution

The reaction is shown below.

Chemistry for Today: General  Organic  and Biochemistry, Chapter 12, Problem 12.27E , additional homework tip  1

Figure 1

The product 2, 3-dibromopentane is prepared by the addition of bromine on 2-pentene. The bromine molecule in non-polar solvent adds on the carbon-carbon double bond of 2-pentene and reduces it to carbon-carbon single bond. The corresponding chemical reaction is shown below.

Chemistry for Today: General  Organic  and Biochemistry, Chapter 12, Problem 12.27E , additional homework tip  2

Figure 2

Conclusion

The structural formula for the alkene with molecular formula C5H10 that gives 2, 3-dibromopentane as product is CH3CH2CH=CHCH3.

Interpretation Introduction

(b)

Interpretation:

The structural formula for the alkene with molecular formula C5H10 that gives CH3CH2CH2CH2CH3 as the product is to be stated.

Concept introduction:

The addition reactions are defined as the formation of one product by the combination of two or more products. For example, in halogenation, the addition of a halogen molecule results in the reduction of carbon-carbon double bond to carbon-carbon single bond and formation of haloalkane.

Expert Solution
Check Mark

Answer to Problem 12.27E

The structural formula for the alkene with molecular formula C5H10 that gives pentane as the product is CH3CH2CH=CHCH3 and CH3CH2CH2CH=CH2.

Explanation of Solution

The reaction is shown below.

C5H10+H2PtCH3CH2CH2CH2CH3

The product in the given reaction is pentane which can be prepared by the hydrogenation on the 1- pentene, and 2- pentene. The hydrogen molecule, in the presence of catalyst, adds on the carbon-carbon double bond of alkenes and reduces it to carbon-carbon single bond. The corresponding chemical reactions are shown below.

CH3CH2CH=CHCH3+H2PtCH3CH2CH2CH2CH3CH3CH2CH2CH=CH2+H2PtCH3CH2CH2CH2CH3

Conclusion

The structural formula for the alkene with molecular formula C5H10 that gives pentane as the product is CH3CH2CH=CHCH3 and CH3CH2CH2CH=CH2.

Interpretation Introduction

(c)

Interpretation:

The structural formula for the alkene with molecular formula C5H10 that gives 2-methylbutan-2-ol as the product is to be stated.

Concept introduction:

The Markovnikov’s rule states that the addition of the HX to the alkene takes place in such a manner that the attachment of hydrogen atom takes place on the carbon atom having more number of hydrogen atoms.

Expert Solution
Check Mark

Answer to Problem 12.27E

The structural formula for the alkene with molecular formula C5H10 that gives 2-methylbutan-2-ol as product is shown below.

Chemistry for Today: General  Organic  and Biochemistry, Chapter 12, Problem 12.27E , additional homework tip  3

Explanation of Solution

The reaction is shown below.

Chemistry for Today: General  Organic  and Biochemistry, Chapter 12, Problem 12.27E , additional homework tip  4

Figure 2

The product in the reaction is 2-methylbutan-2-ol which can be prepared by the addition of H2O molecule on 2-methylbut-2-ene in the presence of H2SO4 by Markovnikov’s rule. The hydroxide ion will attach to the more substituted carbon. The corresponding chemical reaction is shown below.

Chemistry for Today: General  Organic  and Biochemistry, Chapter 12, Problem 12.27E , additional homework tip  5

Figure 3

Conclusion

The structural formula for the alkene with molecular formula C5H10 that gives 2-methylbutan-2-ol as product is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The structural formula for the alkene with molecular formula C5H10 that gives 2-bromopentane as product is to be stated.

Concept introduction:

The Markovnikov’s rule states that the addition of the HX to the alkene takes place in such a manner that the attachment of hydrogen atom takes place on the carbon atom having more number of hydrogen atoms.

Expert Solution
Check Mark

Answer to Problem 12.27E

The structural formula for the alkene with molecular formula C5H10 that gives 2-bromopentane as product is CH2=CHCH2CH2CH3.

Explanation of Solution

The given reaction is shown below.

Chemistry for Today: General  Organic  and Biochemistry, Chapter 12, Problem 12.27E , additional homework tip  6

Figure 4

The product in the given reaction is 2-bromopentane which can be prepared by the addition of HBr molecule on 1-pentene by Markovnikov’s rule. The bromide ion will attach to the more substituted carbon. The corresponding chemical reaction is shown below.

Chemistry for Today: General  Organic  and Biochemistry, Chapter 12, Problem 12.27E , additional homework tip  7

Figure 5

Conclusion

The structural formula for the alkene with molecular formula C5H10 that gives 2-bromopentane as product is CH2=CHCH2CH2CH3.

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Chapter 12 Solutions

Chemistry for Today: General Organic and Biochemistry

Ch. 12 - Prob. 12.11ECh. 12 - Prob. 12.12ECh. 12 - What type of hybridized orbital is present on...Ch. 12 - What type of orbital overlaps to form a pi bond in...Ch. 12 - Prob. 12.15ECh. 12 - Explain the difference between geometric and...Ch. 12 - Draw structural formulas and give IUPAC names for...Ch. 12 - Prob. 12.18ECh. 12 - Which of the following alkenes can exist as...Ch. 12 - Draw structural formulas for the following:...Ch. 12 - Prob. 12.21ECh. 12 - In what ways are the physical properties of...Ch. 12 - Prob. 12.23ECh. 12 - Prob. 12.24ECh. 12 - Complete the following reactions. Where more than...Ch. 12 - Prob. 12.26ECh. 12 - Prob. 12.27ECh. 12 - What reagents would you use to prepare each of the...Ch. 12 - What is an important commercial application of...Ch. 12 - Prob. 12.30ECh. 12 - Terpin hydrate is used medicinally as an...Ch. 12 - Prob. 12.32ECh. 12 - Prob. 12.33ECh. 12 - Prob. 12.34ECh. 12 - Prob. 12.35ECh. 12 - Much of todays plumbing in newly built homes is...Ch. 12 - Prob. 12.37ECh. 12 - What type of hybridized orbital is present on...Ch. 12 - How many sigma bonds and how many pi bonds make up...Ch. 12 - Prob. 12.40ECh. 12 - Explain why geometric isomerism is not possible in...Ch. 12 - Give the common name and major uses of the...Ch. 12 - Describe the physical and chemical properties of...Ch. 12 - Prob. 12.44ECh. 12 - Prob. 12.45ECh. 12 - Prob. 12.46ECh. 12 - Prob. 12.47ECh. 12 - Prob. 12.48ECh. 12 - Limonene, which is present in citrus peelings, has...Ch. 12 - A disubstituted cycloalkane such as a exhibits...Ch. 12 - Prob. 12.51ECh. 12 - Prob. 12.52ECh. 12 - Give an IUPAC name for the following as...Ch. 12 - Give an IUPAC name for the following as...Ch. 12 - Name the following compounds, using the prefixed...Ch. 12 - Name the following compounds, using the prefixed...Ch. 12 - Name the following by numbering the benzene ring....Ch. 12 - Name the following by numbering the benzene ring....Ch. 12 - Prob. 12.59ECh. 12 - Write structural formulas for the following:...Ch. 12 - Prob. 12.61ECh. 12 - Prob. 12.62ECh. 12 - Prob. 12.63ECh. 12 - Prob. 12.64ECh. 12 - Prob. 12.65ECh. 12 - Prob. 12.66ECh. 12 - Prob. 12.67ECh. 12 - Prob. 12.68ECh. 12 - Prob. 12.69ECh. 12 - Prob. 12.70ECh. 12 - Prob. 12.71ECh. 12 - Prob. 12.72ECh. 12 - Prob. 12.73ECh. 12 - Prob. 12.74ECh. 12 - Prob. 12.75ECh. 12 - Prob. 12.76ECh. 12 - Prob. 12.77ECh. 12 - Prob. 12.78ECh. 12 - Prob. 12.79ECh. 12 - Prob. 12.80ECh. 12 - Prob. 12.81ECh. 12 - Prob. 12.82ECh. 12 - Prob. 12.83ECh. 12 - The compound CH2=CHCH2CH2CH3 is an example of: a....Ch. 12 - The correct structural for ethyne is: a. HC=CH b....Ch. 12 - Prob. 12.86E
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