carbon: the backbone of life

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Carbon: The Backbone of Life Living organisms consist mostly of carbon-based compounds Carbon is able to form simple or large, complex, and diverse molecules © 2011 Pearson Education, Inc.

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Fat droplets A fat molecule Part of a human adipose cell Hydrocarbons - organic molecules consisting of only carbon and hydrogen Majority of bonds are nonpolar C-H links that are hydrophobic Reactions release large amounts of energy stored in bonds

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Hydrogen (valence  1) Oxygen (valence  2) Nitrogen (valence  3) Carbon (valence  4) Most organic compounds contain carbon and hydrogen and also oxygen, and nitrogen, (often sulfur, phosphorous too) Carbon - 4 valence electrons ……can form 4 covalent bonds (makes large, complex molecules possible)

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Urea Carbon’s most frequent partners – hydrogen ,oxygen, nitrogen

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Figure 4.5a Ethane Propane Carbon chains vary in length and shape Carbon chains form the skeletons of most organic molecules

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Butane isobutane Carbon skeletons can be straight, branched or rings Cyclohexane Benzene

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Figure 4.5c 1-Butene Carbon chains can vary in Double bond position 2-Butene

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Name and Comment Molecular Formula (a) Methane (b) Ethane CH 4 Ball-and- Stick Model Space-Filling Model (c) Ethene (ethylene) C 2 H 6 C 2 H 4 Structural Formula each carbon bonded to four other atoms has a tetrahedral shape Exception - when two carbon atoms are joined by a double bond

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Isomers - compounds with the same molecular formula but different structures and thus different properties Structural isomers Cis-trans isomers Enantiomers isomers ( mirror images) © 2011 Pearson Education, Inc.

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Figure 4.7a Structural isomers have different covalent arrangements of their atoms and different locations of double bonds (if present) Pentane Methyl butane C 5 H 12

Figure 4.5a:

cis isomer: The two Xs are on the same side. trans isomer: The two Xs are on opposite sides. Cis-trans isomers have covalent bonds to same atoms, but differ in spatial arrangements (inflexibility of double bonds) X 2 C 2 H 2

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Figure 4.7c CO 2 H CO 2 H CH 3 H NH 2 L isomer NH 2 CH 3 H D isomer important in the pharmaceutical industry Enantiomers - isomers that are mirror images of each other to presence of asymmetric carbons = (C attached to 4 different groups)

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Drug Ibuprofen Albuterol Condition Effective Enantiomer Ineffective Enantiomer Pain; inflammation Asthma S -Ibuprofen R -Ibuprofen R -Albuterol S -Albuterol Enantiomers of a drug may have different effects

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Distinctive properties of organic molecules depend on the carbon skeleton and on the molecular components attached to it A number of characteristic groups (called Functional Groups ) can replace the hydrogens attached to skeletons of organic molecules © 2011 Pearson Education, Inc. Functional groups - the components of organic molecules that are most commonly involved in chemical reactions

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Figure 4.UN02 Estradiol Testosterone The number and arrangement of functional groups give each molecule its unique properties

Figure 4.7a:

The 7 functional groups that are most important in the chemistry of life: Hydroxyl group Carbonyl group Carboxyl group Amino group Sulfhydryl group Phosphate group Methyl group © 2011 Pearson Education, Inc. Hydrophilic Nonreactive – serves as a recognizable “tag”

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Figure 4.9a STRUCTURE EXAMPLE Alcohols (Their specific names usually end in -ol .) NAME OF COMPOUND FUNCTIONAL PROPERTIES (may be written HO—) Ethanol • Is polar as a result of the electrons spending more time near the electronegative oxygen atom. • Can form hydrogen bonds with water molecules, helping dissolve organic compounds such as sugars. Hydroxyl

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Figure 4.9b Carbonyl STRUCTURE EXAMPLE Ketones if the carbonyl group is within a carbon skeleton NAME OF COMPOUND FUNCTIONAL PROPERTIES Aldehydes if the carbonyl group is at the end of the carbon skeleton A ketone and an aldehyde may be structural isomers with different properties, as is the case for acetone and propanal. Acetone Propanal Ketone and aldehyde groups are also found in sugars, giving rise to two major groups of sugars: ketoses (containing ketone groups) and aldoses (containing aldehyde groups).

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Carboxyl STRUCTURE EXAMPLE Carboxylic acids, or organic acids NAME OF COMPOUND FUNCTIONAL PROPERTIES Acetic acid • Acts as an acid; can donate an H + because the covalent bond between oxygen and hydrogen is so polar: • Found in cells in the ionized form with a charge of 1– and called a carboxylate ion . Nonionized Ionized Figure 4.9c

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Amino Amines Glycine STRUCTURE EXAMPLE • Acts as a base; can pick up an H + from the surrounding solution (water, in living organisms): NAME OF COMPOUND FUNCTIONAL PROPERTIES • Found in cells in the ionized form with a charge of 1  . Nonionized Ionized Figure 4.9d

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Sulfhydryl Thiols (may be written HS —) STRUCTURE EXAMPLE • Two sulfhydryl groups can react, forming a covalent bond. This “cross-linking” helps stabilize protein structure. NAME OF COMPOUND FUNCTIONAL PROPERTIES • Cross-linking of cysteines in hair proteins maintains the curliness or straightness of hair. Straight hair can be “permanently” curled by shaping it around curlers and then breaking and re-forming the cross-linking bonds. Cysteine Figure 4.9e

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Figure 4.9f Phosphate STRUCTURE EXAMPLE NAME OF COMPOUND FUNCTIONAL PROPERTIES Organic phosphates Glycerol phosphate • Contributes negative charge to the molecule of which it is a part (2– when at the end of a molecule, as at left; 1– when located internally in a chain of phosphates). • Molecules containing phosphate groups have the potential to react with water, releasing energy.

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Figure 4.9g Methyl STRUCTURE EXAMPLE NAME OF COMPOUND FUNCTIONAL PROPERTIES Methylated compounds 5-Methyl cytidine • Addition of a methyl group to DNA, or to molecules bound to DNA, affects the expression of genes. • Arrangement of methyl groups in male and female sex hormones affects their shape and function.

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ATP: Source of Energy for Cellular Processes A denosine T ri p hosphate ( ATP ) ATP consists of an organic molecule called adenosine attached to a string of three phosphate groups © 2011 Pearson Education, Inc. Adenosine

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Figure 4. UN05 Adenosine Adenosine Reacts with H 2 O Inorganic phosphate ATP ADP Energy One phosphate molecule is the primary energy-transferring molecule in the cell

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