Organic Chemistry with a Biological Emphasis Volume II

Format:

Book

Author/Creator:

Soderberg, Tim, author.

Language:

English

Subjects (All):

Science--Textbooks.

Science.

Chemistry--Textbooks.

Chemistry.

Physical Description:

1 online resource

Place of Publication:

Morris, Minnesota University of Minnesota Morris [2016]

Language Note:

In English.

Summary:

The traditional approach to teaching Organic Chemistry, taken by most of the textbooks that are currently available, is to focus primarily on the reactions of laboratory synthesis, with much less discussion - in the central chapters, at least - of biological molecules and reactions. This is despite the fact that, in many classrooms, a majority of students are majoring in Biology or Health Sciences rather than in Chemistry, and are presumably taking the course in order to learn about the chemistry that takes place in living things. In an effort to address this disconnect, I have developed a textbook for a two-semester, sophomore-level course in Organic Chemistry in which biological chemistry takes center stage. For the most part, the text covers the core concepts of organic structure, structure determination, and reactivity in the standard order. What is different is the context: biological chemistry is fully integrated into the explanation of central principles, and as much as possible the in-chapter and end-of-chapter problems are taken from the biochemical literature. Many laboratory synthesis reactions are also covered, generally in parallel with their biochemical counterparts - but it is intentionally the biological chemistry that comes first.

Contents:

Chapter 9: Phosphate transfer reactions

Section 1: Overview of phosphate groups

Section 2: Phosphate transfer reactions - an overview

Section 3: ATP, the principal phosphate group donor

Section 4: Phosphorylation of alcohols

Section 5: Phosphorylation of carboxylates

Section 6: Hydrolysis of organic phosphates

Section 7: Phosphate diesters in DNA and RNA

Section 8: The organic chemistry of genetic engineering

Chapter 10: Nucleophilic carbonyl addition reactions

Section 1: Nucleophilic additions to aldehydes and ketones: an overview

Section 2: Hemiacetals, hemiketals, and hydrates

Section 3: Acetals and ketals

Section 4: N-glycosidic bonds

Section 5: Imines

Section 5: A look ahead: addition of carbon and hydride nucleophiles to carbonyls

Chapter 11: Nucleophilic acyl substitution reactions

Section 1: Carboxylic acid derivatives

Section 2: The nucleophilic acyl substitution mechanism

Section 3: The relative reactivity of carboxylic acid derivatives

Section 4: Acyl phosphates

Section 5: Formation of thioesters, esters, and amides

Section 6: Hydrolysis of thioesters, esters, and amides

Section 7: Protein synthesis on the ribosome

Section 8: Nucleophilic substitution at activated amides and carbamides

Section 9: Nucleophilic acyl substitution reactions in the laboratory

Section 10: A look ahead: acyl substitution reactions with a carbanion or hydride ion nucleophile

Chapter 12: Reactions at the α-carbon, part I

Section 1: Review of acidity at the α-carbon

Section 2: Isomerization at the α-carbon

Section 3: Aldol addition

Section 4: α-carbon reactions in the synthesis lab - kinetic vs. thermodynamic alkylation products

Interchapter: Predicting multistep pathways - the retrosynthesis approachChapter 13: Reactions at the α-carbon, part II

Section 1: Decarboxylation

Section 2: An overview of fatty acid metabolism

Section 3: Claisen condensation

Section 4: Conjugate addition and elimination

Section 5: Carboxylation

Chapter 14: Electrophilic reactions

Section 1: Electrophilic addition to alkenes

Section 2: Elimination by the E1 mechanism

Section 3: Electrophilic isomerization

Section 4: Electrophilic substitution

Section 5: Carbocation rearrangements

Chapter 15: Oxidation and reduction reactions

Section 1: Oxidation and reduction of organic compounds - an overview

Section 2: Oxidation and reduction in the context of metabolism

Section 3: Hydrogenation of carbonyl and imine groups

Section 4: Hydrogenation of alkenes and dehydrogenation of alkanes

Section 5: Monitoring hydrogenation and dehydrogenation reactions by UV spectroscopy

Section 6: Redox reactions of thiols and disulfides

Section 7: Flavin-dependent monooxygenase reactions: hydroxylation, epoxidation, and theBaeyer-Villiger oxidation

Section 8: Hydrogen peroxide is a harmful 'Reactive Oxygen Species'

Chapter 16: Radical reactions

Section 1: Overview of single-electron reactions and free radicals

Section 2: Radical chain reactions

Section 3: Useful polymers formed by radical chain reactions

Section 4: Destruction of the ozone layer by a radical chain reaction

Section 5: Oxidative damage to cells, vitamin C, and scurvy

Section 6: Flavin as a one-electron carrier

Chapter 17: The organic chemistry of vitamins

Section 1: Pyridoxal phosphate (Vitamin B6)

Section 2: Thiamine diphosphate (Vitamin B1)

Section 3: Thiamine diphosphate, lipoamide and the pyruvate dehydrogenase reaction

Section 4: Folate

Notes:

Description based on online resource