Chapter 11, Unsaturated Hydrocarbons  Alkyne

 HC (triple bond) CH (ethyne, acetylene)

 Alkenes and Alkynes:
 CH3-C (triple bond) CH (propyne)
◦ Alkenes ( - ene) and Alkynes (- yne)
 Cis-Trans Isomers:
 Contain double and triple bonds
◦ Cis isomer
 Unsaturated hydrocarbons b/c they do not contain
 The hydrogen atoms are on the same side of the
the max. # of hydrogen atoms
double bond
◦ Alkanes
◦ Trans isomer
 React with hydrogen gas to increase the # of
 The hydrogen atoms are attached on opposite sides
hydrogen atoms
◦ Trans isomers are more stable than their Cis counterparts
 Saturated hydrocarbons b/c they do have the max.
b/c the large groups attached to the double bond are
# of hydrogen atoms
farther apart
◦ Identifying Alkenes and Alkynes
◦ An alkene does not have cis-trans isomers if identical groups
 Alkenes
are attached to either of the carbon atoms in the double
 Contain one or more carbon-carbon double
bond
bonds (ex: ethane (C2H4))
◦ Alkynes do not have cis-trans isomers b/c the carbons in the
 Alkyne
triple bond are each attached to only one group
 A triple bond forms when two carbon
 Addition Reactions
atoms (ex: ethyne (C2H2)) ◦ Addition
◦ Naming Alkenes and Alkynes
 Occurs b/c double and triple bonds are easily
 Steps: broken, providing electrons for new single bonds
 Name the longest carbon chain that ◦ Summary of Addition Reactions
contains the double or triple bond  Hydrogenation – two atoms of hydrogen add to the
 Number the longest chain from the end carbons in a double bond of an alkene to form an
nearest the double or triple bond alkane, and double bonds are converted to single
 Give the location and name of each bonds
substituent (alphabetical order) as a prefix  Alkene + H2
to the alkene or alkyne name o Pt, Ni, Pd
◦ Comparison of Names for Alkanes, Alkenes, and Alkynes
o Alkane
 Alkane
 Alkyne + 2H2
 H3C-CH3 (Ethane)
o Pt, Ni, Pd
 CH3-CH2-CH3 (Propane)
o Alkane
 Alkene
 Hydration – an alkene reacts with water (H-OH)
 H2C=CH2 (ethene, ethylene)
 Alkene + H2O
 CH3-CH=CH2 (propene)
 o H+  Compounds that usually have fragrant odors and
o Alcohol often contain the ring structure of benzene
 Polymers of Alkenes ◦ Benzene
◦ Polymers  A ring of six carbon atoms, each of which is attached
 A very large molecule that is composed of many to a hydrogen atom, C6H6
small, repeating structural units that are identical ◦ Naming Aromatic Compounds
◦ Monomer  Toluene (methylbenzene)
 The small organic molecule that is repeated many  Ethylbenzene
times in a polymer  Aniline (benzenamine)
◦ Some Alkenes and Their Polymers  Phenol (hydroxybenzene)
 CH2 = CH2 (ethane aka. Polyethylene)  Phenyl group
 Plastic bottles, film, and insulation materials ◦ When there are two or more substituent, the benzene ring
 CH2 = CH – Cl (chloroethene aka. Polyvinyl chloride is numbered to give the lowest # to the substituents
(PVC))
Chapter 10, Introduction to Organic Chemistry: Alkanes
 Plastic pipes and tubing, garden hoses, and
garbage bags  Organic chemistry as the study of carbon compounds
 CH2 = CH – CH3 (propene aka. Polypropylene)  Some Properties of Organic and Inorganic Compounds
 Ski and hiking clothing, carpets, and o Organic
artificial joints  C and H, sometimes O, S, N, P, or Cl
 CF2 = CF2 (tetrafluoroethene aka.  Molecules
Polytetrafluoroethylene)  Mostly covalent
 Nonstick coatings  Nonpolar, unless a more electronegative atom is
 CH2 = CCl – Cl (1,1-Dichloroethene aka. present
Polydichloroethylene)  Usually low melting point
 Plastic film and wrap  Usually low boiling point
◦ PETE (Polyethylene terephthalate)  High flammability
◦ HDPE (High-density polyethylene)  Not soluble, unless a polar group is present
◦ PVC (Polyvinyl chloride) o Inorganic
◦ LDPE (Low-density polyethylene)  Most metals and nonmetals
◦ PP (Polypropylene)  Mostly ions
◦ PS (Polystyrene)  Many are ionic, some covalent
 Aromatic Compounds  Most are ionic or polar covalent, a few are nonpolar
◦ Aromatic compounds covalent
 Usually high melting point
  Usually high boiling point o Branch – a carbon group or halogen bonded to the main
 Low flammability carbon chain
 Most are soluble, unless nonpolar o Substituent – groups of atoms such as an alkyl group or a
 Hydrocarbons halogen bonded to the main chain or ring of carbon atoms
o Organic compounds that consist of only carbon and o Branched alkane – a hydrocarbon containing a substituent
hydrogen bonded to the main chain
 Alkanes o Isomers – organic compounds in which identical molecular
o A class of hydrocarbons in which the atoms are connected formulas have different arrangements of atoms
only by single bonds  Substituents in Alkanes
o IUPAC Names for the First Ten Alkanes o CH3 – (Methyl)
 Meth – CH4 o CH3 – CH2 – (Ethyl)
 Eth – C2H6 o CH3 – CH2 – CH2 – (Propyl)
 Prop – C3H8 o CH3 – CH – CH3 (Isopropyl)
 But – C4H10 o F -, Cl -, Br -, I – (Fluoro, chloro, bromo, iodo)
 Pent – C5H12  Rules for Naming Alkanes with Substituents
 Hex – C6H14 o Write the alkane name of the longest chain of carbon atoms
 Hept – C7H16 o Number the carbon atoms starting from the end nearest a
 Oct – C8H18 substituent
 Non- C9H20 o Give the location and name of each substituent as a prefix
 Dec C10H22 to the alkane name (di, tri, tetra)
o Expanded structural formula
 Properties of Alkanes
 Written when we show the bonds b/t all of the o Alkanes
atoms
 Nonpolar, insoluble in water
o Condensed structural formula
 Soluble in nonpolar solvents such as other alkanes
 Each carbon atom and its attached hydrogen atoms  Densities from 0.62 g/mL to about 0.79 g/mL
are written as a group  Four alkanes – methane, ethane, propane, and
 Cycloalkanes butane are gases at room temp. and are widely
o Two fewer hydrogen atoms than the corresponding alkanes used as heating fuels
o Formula of Some Common Cycloalkanes  Five alkanes – pentane, hexane, heptanes, and
 Cyclopropane (3 carbon) octane are liquids at room temp.
 Cyclobutane (4 carbon)  Eight alkanes – nonane and decane have higher
 Cyclopentane (5 carbon) boiling points
 Cyclohexane (6 carbon)  Alkanes with 18 or more carbon atoms are waxy
 Alkanes with Substituents solids as room temp.
 Combusting of Alkanes  Carbonyl group (carbon-oxygen double
o Alkane undergoes combustion when it completely reacts bond) b/t carbon atoms
with oxygen to produce carbon dioxide, water, and energy  Carboxylic acid
 Ex: Alkane + O2 = CO2 + H2O + Energy  Carboxyl group (carbon-oxygen double
 Functional Groups – a group of atoms that determine the physical bond and –OH)
and chemical properties and naming of a class of organic  Ester
compounds  Carboxyl group with –H replaced by a
o Alkenes carbon
 Contain one or more double bonds b/t carbon  Amine
atoms  Nitrogen atom with one or more carbon
o Alkynes groups
 Contain triple bonds  Amide
o Aromatic compounds  Carbonyl group bonded to nitrogen
 Contain benzene, a molecule that has a ring of six
Chapter 8, Buffers
carbon atoms with one hydrogen atom attached to
each carbon  Buffer
o Classification of Organic Compounds o A solution that maintains pH by neutralizing added acid or
 Alkene base
 Carbon-carbon double bond o Consist of nearly equal concentrations of a weak acid
 Alkyne (donates H+) and its conjugate base or a weak base (accepts
 Carbon-carbon triple bond H+) and its conjugate acid
 Aromatic o The acid neutralizes added OH- and the base neutralizes
 Benzene ring (six carbon atoms and six added H3O+
hydrogen atoms) o Important in maintaining the pH of the blood
 Alcohol
 Hydroxyl group (-OH) Chapter 15, Lipids
 Ether
 Lipids
 Oxygen atom bonded to two carbons
o A family of biomolecules that have the common property of
 Thiol
being soluble in organic solvents but not in water
 A –SH group bonded to carbon
o Fat or lard
 Aldehyde
o Content of a cell can be extracted using a nonpolar solvent
 Carbonyl group (carbon-oxygen double
such as ether or chloroform
bond) with –H
o An important feature in cell membrane, fat-soluble
 Ketone
vitamins, and steroid hormones
 Types of Lipids o The long carbon chain has one double bond, which makes
o Waxes, fats, oils, and glycerophospholipids are esters that its properties similar to an alkene
can be hydrolyzed to give fatty acids along with other  Polyunsaturated fatty acid
products including an alcohol o There are at least two carbon-carbon double bonds
o Steroids are characterized by the steroid nucleus of four  Structures and Melting Points of Common Fatty Acids:
fused carbon rings. They do not contain fatty acids and o Saturated Fatty Acids
cannot be hydrolyzed  Lauric Acid (coconut)
o Lipids  CH3-(CH2)10-COOH
 Fatty acids  Myristic Acid (nutmeg)
 Prostaglandins  CH3-(CH2)12-COOH
 Waxes  Palmitic Acid (palm)
o Fatty acid  CH3-(CH2)14-COOH
o Long-chain alcohol  Stearic Acid (animal fat)
 Triacylglycerols  CH3-(CH2)16-COOH
o Glycerol o Monounsaturated Fatty Acids (only one double bond)
o 3 fatty acid  Palmitoleic Acid (butter)
 Glycerophospholipids  CH3-(CH2)5-CH=CH-(CH2)7-COOH
o Glycerol  Oleic Acid (olives, corn)
o 2 fatty acid  CH3-(CH2)7-CH=CH-(CH2)7-COOH
o PO4 o Polyunsaturated Fatty Acids (many double bond)
o Amino alcohol  Linoleic Acid (soybean, safflower, and sunflower)
 Steroids  CH3-(CH2)4-CH=CH-CH2-CH=CH-(CH2)7-COOH
o Cholesterol  Linolenic Acid (corn)
o Steroid hormones  CH3-CH2-CH=CH-CH2-CH=CH-CH2-CH=CH-
 Fatty Acids (CH2)7-COOH
o Contain a long, unbranched carbon chain attached to a  Arachidonic Acid (meat, eggs, and fish)
carboxylic acid group at one end  CH3-(CH2)3-(CH2-CH=CH)4-(CH2)3-COOH
o Even number of carbon atoms, usually b/t 10 and 20 (ex:  Physical Properties of Fatty Acids
lauric acid) o Saturated fatty acid
 Saturated fatty acid  Fit close together in a regular pattern, which allows
o The long carbon chain is like an alkane b/c there are only strong attractions to occur b/t the carbon chains
single carbon-carbon bonds  A significant amount of energy and high temp. are
 Monounsaturated fatty acid required to separate the fatty acids and melt the fat
  Length of the carbon chain increases, more  CH2-O-C=O
interactions occur b/t the carbon chains, requiring  Triacylglycerol, three hydroxyl groups of glycerol
higher melting points form ester bonds with the carboxyl groups of fatty
 Usually solids at room temp. acid
o Unsaturated fatty acid o Most fats and oils are mixed triacylglycerols that contain
 The cis double bond cause the carbon chain to bend two or three different fatty acids
or kink, giving the molecules an irregular shape o Triacylglycerols are the major form of energy storage for
 Fewer interactions occur b/t carbon chains animals
 Less energy is required to separate the molecules,  Melting Points of Fats and Oil
making the melting points of unsaturated fats lower o Fat is a triacylglycerol that is solid at room temp, and usually
than those of saturated fats comes from animal sources such as meat, whole milk,
 Liquid oils at room temp. butter, and cheese
 Prostaglandins o Oil is a triacylglycerol that is usually a liquid room temp. and
o Hormone-like substance produced in low amounts in most is obtained from a plant source
cells of the body o Saturated fatty acids have higher melting points than
 Waxes, Fats, and Oils unsaturated fatty acids b/c they pack together more tightly.
o Waxes are found in  Chemical Properties of Triacylglycerols
 Many plants and animals o Hydrogenation
 An ester of a saturated fatty acid  Unsaturated fat
 Long-chain alcohol, each containing from 14 to 30  Hydrogen is added to carbon-carbon double bonds
carbon atoms to form carbon-carbon single bond
o Some Typical Waxes  -CH=CH- + H2  CH2-CH2
 Beeswax (candles, shoe polish, and wax paper) o Hydrolysis
 CH3(CH2)14-(C=O)-O-(CH2)29CH3  Split by water in the presence of strong acids or
 Carnauba wax (waxes for furniture, cars, floors, and digestive enzymes called lipases
shoes)  Products of hydrolysis of the ester bonds are
 CH3(CH2)24-(C=O)-O-(CH2)29CH3 glycerol and three fatty acids
 Jojoba wax (candles, soaps, and cosmetics)  Polar glycerol is soluble in water, but the fatty acids
 CH3(CH2)19-(C=O)-O-(CH2)19CH3 with their long hydrocarbon chains are not
 Fats and Oils: Triacylglycerols  CH2-O-(C=O)-(CH2)14CH3 + 3H2O  CH2-OH +
o Fatty acids stored as fats and oils known as triacylglycerols 3HO-(C=O)-(CH2)14CH3
o Triacylglycerol: o Saponification
 CH2-O-C=O
 CH-O-C=O
  Fat is heated with a strong base such as sodium o Lipoproteins:
hydroxide, saponification of the fat gives glycerol  Made more soluble by combing them with
and the sodium salts of the fatty acids glycerophospholipids and proteins to form water-
 Fat or oil + Strong base (NaOH)  glycerol + salts of soluble complexes
fatty acids (soaps)  Spherical particles with an outer surface of polar
 Glycerophospholipids: proteins and glycerophospholipids that surround
o A family of lipids similar to triacylglycerols except that one hundreds of nonpolar molecules of triacyglycerols
hydroxyl group of glycerol is replalced by the ester of and cholesteryl esters
phosphoric acid and an amino alcohol, bonded through a  LDL (low density lipoprotein)
phosphodiester bond  Bad cholesterol
o Three amino alcohols found in glycerophospholipids:  HDL (high density lipoprotein)
 Choline  Good cholesterol
 Serine  Steroid Hormones:
 Ethanolamine o Hormones are chemical messenger that serve as a kind of
o Lecithins and cephalins are two types of communication system from one part of the body to
glycerophospholipids that are particularly abundant in brain another
and nerve tissue o Steroid hormones, which include the sex hormones and the
 Lecithins contain choline adrenocortical hormones
 Cephalins contain ethanolamine and sometimes o Male sex hormones:
serine  Testosterone and androsterone
 Sterioids: Cholesterol and Steroid Hormones  Promote the growth of muscle and of facial
o Steroids hair and the maturation of the male sex
 Compounds containing the steroid nucleus, which organs and of sperm
consists of three cyclohexane rings and one o Female sex hormones:
cyclopentane ring fused together  Estrogens
o Cholesterol  Direct the development of female sexual
 One of the most important and abundant steroids characteristics, the uterus increase in size,
in the body fat is deposited in the breasts, and the
 Contain an oxygen atom as a hydroxyl (-OH) group pelvis broadens
on carbon 3  Progesterone
 Methyl group at carbons 10 and 13, and a carbon  Prepares the uterus for the implantation of
chain at carbon 17 and double bond b/t carbons 5 a fertilized egg
and 6  Adrenal Corticosteroids
 Lipoproteins: transport of lipids o Aldosterone
  A mineralocorticoid
 Responsible for electrolyte and water balance by
the kidneys
o Cortisone
 A glucocorticoid
 Increases the blood glucose level and stimulates the
synthesis of glycogen in the liver form amino acids
 Cell Membranes:
o Main components of a cell membrane is
glycerophospholipids
o Two rows (lipid bilayer)
 Hydrophobic
 Nonpolar tails
 Water-fearing
 Move to the center
 Hydrophilic
 Polar heads
 Water-loving
 Align on the outer edges of the membrane
o Lipid bilayer contain unsaturated fatty acids
 Fluid Mosaic Model
o Proteins known as peripheral proteins emerge on just one
of the surfaces, outer or inner
o Integral proteins extend through the entire lipid bilayer and
appear on both surfaces of the membrane
o The concept that cell membranes are lipid bilayer structures
that contain an assortment of polar lipid and proteins in a
dynamic, fluid arrangement
 Transport through cell membranes:
o Facilitated transport increases the rate of diffusion for
substances that diffuse too slowly by passive diffusion to
meet cell needs