Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 5, Problem 34P

(a)

Interpretation Introduction

Interpretation:

The number of alkenes used to prepare methylcyclopentane by hydrogenation process has to be predicted.

Concept introduction:

  • The amount of heat released in a hydrogenation reaction is known as heat of hydrogenation(ΔH0).
  • The most stable alkene has the smallest heat of hydrogenation.
  • The stability of an alkene increases as the number of alkyl substituents bonded to its sp2 carbon increases.
  • The stability of an alkene increases as the number of hydrogen bonded to its sp2 carbon decreases.
    • Catalytic hydrogenation is the process of addition of hydrogen to a compound in the presence of a catalyst.  The most common metal catalyst is palladium, which is used as a powder absorbed on charcoal to maximize its surface area.  The metal catalyst is required to weaken the very strong HH bond.
    • A meso compound is a molecule with multiple stereocentres that is super imposable on its mirror image.

(b)

Interpretation Introduction

Interpretation:

Most stable alkene has to be identified.

Concept introduction:

The amount of heat released in a hydrogenation reaction is known as heat of hydrogenation(ΔH0).

The most stable alkene has the smallest heat of hydrogenation.

The stability of an alkene increases as the number of alkyl substituents bonded to its sp2 carbon increases.

The stability of an alkene decreases as the number of hydrogen bonded to its sp2 carbon decreases.

(c)

Interpretation Introduction

Interpretation:

The alkene which has the smallest heat of hydrogenation has to be identified.

Concept introduction:

The amount of heat released in a hydrogenation reaction is known as heat of hydrogenation(ΔH0).

The most stable alkene has the smallest heat of hydrogenation.

The stability of an alkene increases as the number of alkyl substituents bonded to its sp2 carbon increases.

The stability of an alkene decreases as the number of hydrogen bonded to its sp2 carbon decreases.

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Students have asked these similar questions
Which is the most stable: 3,4-dimethyl-2-hexene, 2,3-dimethyl-2-hexene, or 4,5-dimethyl-2-hexene? a. Which compound has the largest heat of hydrogenation? b. Which compound has the smallest heat of hydrogenation?
Draw the alkene that would react with the reagent given to account for the product formed. ? + + H₂O **** H₂S04 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. CH3 CH3 CHCCH3 | | OH CH3 +1
Draw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reaction occurs. a.H2 + Pd-C b.H2 + Lindlar catalyst c.Na, NH3 d.CH3CO3H e.[1] CH3CO3H; [2] H2O, HO− f.[1]OsO4 + NMO; [2] NaHSO3, H2O g.KMnO4, H2O, HO− h.[1] LiAlH4; [2] H2O i. [1] O3; [2] CH3SCH3 j.(CH3)3COOH, Ti[OCH(CH3)2]4, (−)-DET k.mCPBA l.Product in (k); then [1] LiAlH4; [2] H2O

Chapter 5 Solutions

Essential Organic Chemistry, Global Edition

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