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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
Publisher: Cengage Learning,
ISBN: 9781305081079
BuyFind

Organic And Biological Chemistry

7th Edition
STOKER + 1 other
Publisher: Cengage Learning,
ISBN: 9781305081079

Solutions

Chapter
Section
Chapter 1, Problem 1.124EP
Textbook Problem
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Which member in each of the following pairs of compounds has the higher boiling point?

  1. a. Methane and ethane
  2. b. Cyclohexane and hexane
  3. c. Butane and methylpropane
  4. d. Pentane and 2,2-dimethylpropane

Expert Solution

(a)

Interpretation Introduction

Interpretation:

The member that has higher boiling point in the given pair has to be identified.

Concept Introduction:

Organic compounds are represented shortly by the molecular formula and structural formula.  Each and every compound has its own molecular formula.  Compounds can have same molecular formula but not same structural formula.

Alkanes are linear chain saturated hydrocarbons and cycloalkanes are cyclic carbon chain saturated hydrocarbons.  They both occur naturally.

Alkanes and cycloalkanes are hydrocarbons.  They are nonpolar molecules.  Water is a polar molecule.  Therefore, alkanes and cycloalkanes do not get solubilized in water.  In other words, alkanes and cycloalkanes are insoluble in water.

Regarding density, alkanes and cycloalkanes have density lower than water.  When alkanes and cycloalkanes are mixed with water, two layers are formed which is a result of insolubility.  Alkanes and cycloalkanes are present on top of water layer which is due to lesser density.

Boiling point of alkanes and cycloalkanes increase with an increase in carbon‑chain length or the ring size.  When considering the continuous‑chain alkanes, the boiling point of alkanes increases about 30°C for every carbon atom that is added to the chain.  The continuous alkanes which contain one to four carbon atoms are gases at room temperature.  The continuous chain alkanes that contain five to seventeen carbon atoms are liquids at room temperature.  The continuous chain alkanes that contain more than eighteen carbon atoms are solids at room temperature.

When branching happens in the carbon chain, it lowers the boiling point of alkanes.  In simple words, unbranched alkanes have more boiling point than branched alkanes with the same number of carbon atoms.

Cycloalkanes have higher boiling point compared to noncyclic alkanes with the same number of carbon atoms.  This is due to the more rigid and more symmetrical structures that occur in cyclic systems.  Cyclopropane and cyclobutane are gases at room temperature.  Cyclopentane to cyclooctane are liquids at room temperature.

Explanation of Solution

When considering the continuous‑chain alkanes, the boiling point of alkanes increases about 30°C for every carbon atom that is added to the chain.  Given compounds are ethane and methane

Expert Solution

(b)

Interpretation Introduction

Interpretation:

The member that has higher boiling point in the given pair has to be identified.

Concept Introduction:

Organic compounds are represented shortly by the molecular formula and structural formula.  Each and every compound has its own molecular formula.  Compounds can have same molecular formula but not same structural formula.

Alkanes are linear chain saturated hydrocarbons and cycloalkanes are cyclic carbon chain saturated hydrocarbons.  They both occur naturally.

Alkanes and cycloalkanes are hydrocarbons.  They are nonpolar molecules.  Water is a polar molecule.  Therefore, alkanes and cycloalkanes do not get solubilized in water.  In other words, alkanes and cycloalkanes are insoluble in water.

Regarding density, alkanes and cycloalkanes have density lower than water.  When alkanes and cycloalkanes are mixed with water, two layers are formed which is a result of insolubility.  Alkanes and cycloalkanes are present on top of water layer which is due to lesser density.

Boiling point of alkanes and cycloalkanes increase with an increase in carbon‑chain length or the ring size.  When considering the continuous‑chain alkanes, the boiling point of alkanes increases about 30°C for every carbon atom that is added to the chain.  The continuous alkanes which contain one to four carbon atoms are gases at room temperature.  The continuous chain alkanes that contain five to seventeen carbon atoms are liquids at room temperature.  The continuous chain alkanes that contain more than eighteen carbon atoms are solids at room temperature.

When branching happens in the carbon chain, it lowers the boiling point of alkanes.  In simple words, unbranched alkanes have more boiling point than branched alkanes with the same number of carbon atoms.

Cycloalkanes have higher boiling point compared to noncyclic alkanes with the same number of carbon atoms.  This is due to the more rigid and more symmetrical structures that occur in cyclic systems.  Cyclopropane and cyclobutane are gases at room temperature.  Cyclopentane to cyclooctane are liquids at room temperature.

Expert Solution

(c)

Interpretation Introduction

Interpretation:

The member that has higher boiling point in the given pair has to be identified.

Concept Introduction:

Organic compounds are represented shortly by the molecular formula and structural formula.  Each and every compound has its own molecular formula.  Compounds can have same molecular formula but not same structural formula.

Alkanes are linear chain saturated hydrocarbons and cycloalkanes are cyclic carbon chain saturated hydrocarbons.  They both occur naturally.

Alkanes and cycloalkanes are hydrocarbons.  They are nonpolar molecules.  Water is a polar molecule.  Therefore, alkanes and cycloalkanes do not get solubilized in water.  In other words, alkanes and cycloalkanes are insoluble in water.

Regarding density, alkanes and cycloalkanes have density lower than water.  When alkanes and cycloalkanes are mixed with water, two layers are formed which is a result of insolubility.  Alkanes and cycloalkanes are present on top of water layer which is due to lesser density.

Boiling point of alkanes and cycloalkanes increase with an increase in carbon‑chain length or the ring size.  When considering the continuous‑chain alkanes, the boiling point of alkanes increases about 30°C for every carbon atom that is added to the chain.  The continuous alkanes which contain one to four carbon atoms are gases at room temperature.  The continuous chain alkanes that contain five to seventeen carbon atoms are liquids at room temperature.  The continuous chain alkanes that contain more than eighteen carbon atoms are solids at room temperature.

When branching happens in the carbon chain, it lowers the boiling point of alkanes.  In simple words, unbranched alkanes have more boiling point than branched alkanes with the same number of carbon atoms.

Cycloalkanes have higher boiling point compared to noncyclic alkanes with the same number of carbon atoms.  This is due to the more rigid and more symmetrical structures that occur in cyclic systems.  Cyclopropane and cyclobutane are gases at room temperature.  Cyclopentane to cyclooctane are liquids at room temperature.

Expert Solution

(d)

Interpretation Introduction

Interpretation:

The member that has higher boiling point in the given pair has to be identified.

Concept Introduction:

Organic compounds are represented shortly by the molecular formula and structural formula.  Each and every compound has its own molecular formula.  Compounds can have same molecular formula but not same structural formula.

Alkanes are linear chain saturated hydrocarbons and cycloalkanes are cyclic carbon chain saturated hydrocarbons.  They both occur naturally.

Alkanes and cycloalkanes are hydrocarbons.  They are nonpolar molecules.  Water is a polar molecule.  Therefore, alkanes and cycloalkanes do not get solubilized in water.  In other words, alkanes and cycloalkanes are insoluble in water.

Regarding density, alkanes and cycloalkanes have density lower than water.  When alkanes and cycloalkanes are mixed with water, two layers are formed which is a result of insolubility.  Alkanes and cycloalkanes are present on top of water layer which is due to lesser density.

Boiling point of alkanes and cycloalkanes increase with an increase in carbon‑chain length or the ring size.  When considering the continuous‑chain alkanes, the boiling point of alkanes increases about 30°C for every carbon atom that is added to the chain.  The continuous alkanes which contain one to four carbon atoms are gases at room temperature.  The continuous chain alkanes that contain five to seventeen carbon atoms are liquids at room temperature.  The continuous chain alkanes that contain more than eighteen carbon atoms are solids at room temperature.

When branching happens in the carbon chain, it lowers the boiling point of alkanes.  In simple words, unbranched alkanes have more boiling point than branched alkanes with the same number of carbon atoms.

Cycloalkanes have higher boiling point compared to noncyclic alkanes with the same number of carbon atoms.  This is due to the more rigid and more symmetrical structures that occur in cyclic systems.  Cyclopropane and cyclobutane are gases at room temperature.  Cyclopentane to cyclooctane are liquids at room temperature.

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Chapter 1 Solutions

Organic And Biological Chemistry
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Ch. 1.5 - Which of the following is an incorrect structural...Ch. 1.5 - The bond line in the structural formula CH3CH3...Ch. 1.6 - Isomers are compounds that have a. the same...Ch. 1.6 - One of the two four-carbon alkane constitutional...Ch. 1.6 - Constitutional isomers become possible in alkanes...Ch. 1.6 - How many of the three constitutional isomeric...Ch. 1.7 - How many branches are present in the alkane with...Ch. 1.7 - The structural formulas represent a. two alkane...Ch. 1.8 - The relationship between an alkyl group and its...Ch. 1.8 - The name for the alkyl group CH3CH2CH2 is a....Ch. 1.8 - Which of the following statements about IUPAC...Ch. 1.8 - The IUPAC name for the alkane is a. methane...Ch. 1.8 - The IUPAC name for the alkane is a....Ch. 1.8 - Which of the following alkanes contains eight...Ch. 1.8 - The number of alkyl groups and the number of...Ch. 1.9 - How many carbon atoms are present in the alkane ?...Ch. 1.9 - The line-angle structural formula for the alkane,...Ch. 1.10 - A secondary carbon atom is directly bonded to how...Ch. 1.10 - In which of the following alkanes are both 2 and 3...Ch. 1.11 - The number of different three-carbon and...Ch. 1.11 - Which of the following is not a representation for...Ch. 1.11 - Which of the following is a representation for a...Ch. 1.12 - When the molecular formulas for cyclic and...Ch. 1.12 - How many carbon atoms are present in the...Ch. 1.12 - How many hydrogen atoms are present in a...Ch. 1.13 - The IUPAC name for the cycloalkane is a....Ch. 1.13 - Which of the following cycloalkanes does not...Ch. 1.13 - Which of the following is an incorrect IUPAC name...Ch. 1.14 - How many constitutional isomers are possible for a...Ch. 1.14 - For which of the following cycloalkanes is...Ch. 1.14 - Which of the following cycloalkane structures has...Ch. 1.15 - Which of the following statements concerning...Ch. 1.15 - Which of the following is not a mixture of cyclic...Ch. 1.16 - Which of the following is a general physical...Ch. 1.16 - Which of the following statements concerning...Ch. 1.16 - Which of the following alkanes is a gas at room...Ch. 1.17 - The most important chemical use for alkanes...Ch. 1.17 - The chemical products formed when an alkane...Ch. 1.17 - Which of the following is not a product when an...Ch. 1.17 - Which of the following statements concerning the...Ch. 1.18 - What is the IUPAC name for the compound whose...Ch. 1.18 - What is the common name for the compound whose...Ch. 1.18 - The halogenated methanes methylene chloride and...Ch. 1.18 - A Freon is a halogenated methane in which both a....Ch. 1 - Indicate whether each of the following statements...Ch. 1 - Indicate whether each of the following statements...Ch. 1 - Indicate whether each of the following compounds...Ch. 1 - Indicate whether each of the following compounds...Ch. 1 - Indicate whether each of the following situations...Ch. 1 - Indicate whether each of the following situations...Ch. 1 - What is the difference between a hydrocarbon and a...Ch. 1 - Contrast hydrocarbons and hydrocarbon derivatives...Ch. 1 - What is the difference between a saturated...Ch. 1 - What structural feature is present in an...Ch. 1 - Classify each of the following hydrocarbons as...Ch. 1 - Classify each of the following hydrocarbons as...Ch. 1 - Using the general formula for an alkane, derive...Ch. 1 - Using the general formula for an alkane, derive...Ch. 1 - Convert the following expanded structural formulas...Ch. 1 - Convert the following expanded structural formulas...Ch. 1 - Convert the expanded structural formulas in...Ch. 1 - Convert the expanded structural formulas in...Ch. 1 - Convert the expanded structural formulas in...Ch. 1 - Convert the expanded structural formulas in...Ch. 1 - Draw the indicated type of formula for the...Ch. 1 - Draw the indicated type of formula for the...Ch. 1 - Determine the following for the six-carbon alkane...Ch. 1 - Determine the following for the five-carbon alkane...Ch. 1 - What, if anything, is wrong with the following...Ch. 1 - 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How many of the nine C7 alkane constitutional...Ch. 1 - Convert each of the following line-angle...Ch. 1 - Convert each of the following line-angle...Ch. 1 - Convert each of the following line-angle...Ch. 1 - Convert each of the following line-angle...Ch. 1 - Do the line-angle structural formulas in each of...Ch. 1 - Do the line-angle structural formulas in each of...Ch. 1 - Convert each of the condensed structural formulas...Ch. 1 - Convert each of the condensed structural formulas...Ch. 1 - Assign an IUPAC name to each of the compounds in...Ch. 1 - Assign an IUPAC name to each of the compounds in...Ch. 1 - Determine the molecular formula for each of the...Ch. 1 - Determine the molecular formula for each of the...Ch. 1 - For each of the alkane structures in Problem...Ch. 1 - For each of the alkane structures in Problem...Ch. 1 - Indicate whether or not both 2 and 3 carbon atoms...Ch. 1 - Indicate whether or not both 2 and 3 carbon atoms...Ch. 1 - Draw the condensed structural formula for an...Ch. 1 - Draw the condensed structural formula for an...Ch. 1 - Give the name of the branched alkyl group attached...Ch. 1 - Give the name of the branched alkyl group attached...Ch. 1 - Draw condensed structural formulas for the...Ch. 1 - Draw condensed structural formulas for the...Ch. 1 - To which carbon atoms in a hexane molecule can...Ch. 1 - To which carbon atoms in a heptane molecule can...Ch. 1 - Using IUPAC rules, name the following complex...Ch. 1 - Using IUPAC rules, name the following complex...Ch. 1 - Give an acceptable alternate name for each of the...Ch. 1 - Give an acceptable alternate name for each...Ch. 1 - How many different alkyl groups exist that contain...Ch. 1 - How many different alkyl groups exist that contain...Ch. 1 - Using the general formula for a cycloalkane,...Ch. 1 - Using the general formula for a cycloalkane,...Ch. 1 - What is the molecular formula for each of the...Ch. 1 - What is the molecular formula for each of the...Ch. 1 - How many alkyl groups are present in each of the...Ch. 1 - 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Assign an IUPAC name to each of the following...Ch. 1 - Assign an IUPAC name to each of the following...Ch. 1 - Name each of the compounds in Problem 12-135 as an...Ch. 1 - Name each of the compounds in Problem 12-136 as an...Ch. 1 - Draw structural formulas for the following...Ch. 1 - Draw structural formulas for the following...Ch. 1 - Indicate whether each of the following molecular...Ch. 1 - Indicate whether each of the following molecular...Ch. 1 - Which member of each of the following pairs of...Ch. 1 - Which member of each of the following pairs of...Ch. 1 - Indicate whether or not the following halogenated...Ch. 1 - Indicate whether or not the following halogenated...Ch. 1 - Give the IUPAC names for the eight isomeric...Ch. 1 - Give the IUPAC names for the nine isomeric...

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