(a) Interpretation: 2-methylbutane, pentane and 2,2-dimethylpropane should be arranged in increasing order of boiling point. Concept Introduction: The compound containing longest parent chain of carbon having high boiling point due to the bulkiness of the structure while the compound containing shortest parent chain of carbon having low boiling point. Moreover, straight chain has large surface area which increases the possibility of area of contact with other chain which results in higher Vander Waal forces between them and thus increases the boiling point. Thus, on increasing branching, due to decrease in surface area, boiling point decreases.

Question

PROBLEM 11-38 Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethyleyclopentane f (c) OCH, CH₂ (e) OCH₂CH₂ C-CH₂CH₂ (1) OCH,

Answer 1

Question

Chapter 11.9, Problem 11.8P

Interpretation Introduction

(a)

Interpretation:

2-methylbutane, pentane and 2,2-dimethylpropane should be arranged in increasing order of boiling point.

Concept Introduction:

The compound containing longest parent chain of carbon having high boiling point due to the bulkiness of the structure while the compound containing shortest parent chain of carbon having low boiling point.

Moreover, straight chain has large surface area which increases the possibility of area of contact with other chain which results in higher Vander Waal forces between them and thus increases the boiling point.

Thus, on increasing branching, due to decrease in surface area, boiling point decreases.

Interpretation Introduction

(b)

Interpretation:

3,3-dimethylheptane, nonane, 2,2,4-trimethylhexane should be arranged according to increasing boiling point.

Concept Introduction:

The compound containing longest parent chain of carbon having high boiling point due to the bulkiness of the structure while the compound containing shortest parent chain of carbon having low boiling point.

Moreover, straight chain has large surface area which increases the possibility of area of contact with other chain which results in higher Vander Waal forces between them and thus increases the boiling point. Thus, on increasing branching, due to decrease in surface area, boiling point decreases.

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PROBLEM 11-38 Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethyleyclopentane f (c) OCH, CH₂ (e) OCH₂CH₂ C-CH₂CH₂ (1) OCH,

PROBLEM 3-11 Draw a graph, similar to Figure 3-9, of the torsional strain of 2-methylpropane as it rotates about the bond between C1 and C2. Show the dihedral angle and draw a Newman projection for each staggered and eclipsed conformation.

Part A Give the name for the structure in the image shown: CH;CH, CH,CH3 CH3CCH,CH CH3 CH3 O 2,4-dimethyl-2,4-diethylbutane O 3,5,5-trimethylheptane O 1,3-dimethyl-1,3-diethylbutane O 3,3,5-trimethylheptane Submit Request Answer Part B Give the name for the structure in the image shown: CH3 CH;CH,CH,ĊCH3 CH;CHCH,CH3 4,4,5-trimethylheptane O 2-methyl-2-butyl-2-pentane O 3,4,4-trimethylheptane O 2,3-dimethyl-2-propyl-2-pentane