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Organic Chemistry:Carbon and the Molecular
Diversity of Life
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Organic chemistry is the study of carbon compoundsOrganic compounds range from simple molecules to colossal ones.
Most organic compounds contain hydrogen atoms in addition to carbon atoms.
Compounds containing only carbon and hydrogen are called hydrocarbons; they are commonly used as a fuel source.
Organic Chemistry
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Carbon is the backbone of biological molecule.
Carbon has the ability to form long chains.
This property allows the formation of large biomolecules (such as proteins, lipids, carbohydrates, and nucleic acids).
Biological Molecules
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Carbon has four valence electrons to make covalent bonds
Carbon atoms can form diverse molecules by bonding to four other atoms
Recall that electron configuration is the key to an atom’s characteristics because it determines the kinds of bonds and number of bonds an atom will form with other atoms
Carbon
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1 Organic chemistry is a science based on the study of ___________________.
A compounds that can only be made by living cells.B vital forces interacting with matter.
C carbon compounds.
D water and its interaction with other kinds of molecules.
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2 Which property of the carbon atom allows it to bond with many different elements?
A Carbon has 6 to 8 neutrons.
B Carbon has 4 valence electrons.C Carbon forms ionic bonds.D A and C onlyE A, B, and C
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3 How many electron pairs does carbon share in order to complete its valence shell?
A 1B 2C 3D 4E 8
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4 What type/s of bond/s does carbon have a tendency to form?
A IonicB HydrogenC Covalent
D A and B E A, B and C
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Hydrocarbons are compounds made up of carbon and hydrogen atoms
Aliphatic hydrocarbons: compounds with carbon atoms connected in a straight chain
Aliphatic compounds consist of three classes of compounds: Alkanes Alkenes Alkynes
Aromatic hydrocarbons: compounds with carbon atoms connected in cyclic (ringed) structures that have an odor
Hydrocarbons
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Hydrocarbon chains where all the bonds between carbons are SINGLE bonds
They are also known as saturated hydrocarbons. They are “saturated” with hydrogens.
Aliphatic hydrocarbons: Alkanes
Examples: Methane, Propane, Butane, OctaneName uses the ending -ane
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Alkanes
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The general formula CnH2n+2
n = number of carbon atoms
Alkanes
______ Hexane
______ Heptane
______ Octane
______ Nonane
______ Decane
CH4 Methane
C2H6 Ethane
C3H8 Propane
C4H10 Butane
C5H12 Pentane
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Straight Chain Alkanes
Straight chain alkanes are alkanes that have all their carbon atoms connected in a row.
These are structural formulas.
CH3-CH2-CH3 This is a condensed formula for propane.
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Branched chain alkanes are alkanes that have a branching connection of carbons.
For example, butane has the formula C4H10.
Shown below are the straight chain and branched forms of butane.
Branched Chain Alkanes
CH3-CH2-CH2-CH3
Straight chain butane Branched chain butane
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Hydrocarbons are non polar, since the difference in electronegativity between C and H is below 0.5. Note that larger molecules are more polarizable and therefore have stronger London dispersion forces which increases boiling point.
Alkanes
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5 What is the reason why hydrocarbons are not soluble in water?
A The majority of their bonds are polar covalent C-H linkages
B The majority of their bonds are nonpolar covalent C-H linkages
C They are hydrophilic
D They exhibit considerable molecular complexity and diversity
E They are lighter than water
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6 Gasoline and water do not mix because gasoline is __________.
A less dense than water
B less viscous than wtaer
C nonpolar and water is polar
D volatile and water is not
E polar and water is nonpolar
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7 Which substance would be the most soluble in gasoline?
A waterB sodium nitrate, NaNO3
C hydochloric acid, HClD hexane, C6H14
E sodium chloride, NaCl
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Ethene
Alkenes have at least one double bond between two carbon atoms. General formula: CnH2n where n = # of carbon atoms
The name uses the ending -ene.
The simplest alkenes are:
C2H4 Ethene (from 2-carbon parent, ethane)
C3H6 Propene (from 3-carbon parent, propane)
Aliphatic hydrocarbons: Alkenes
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Alkynes have at least one triple bond between two carbon atoms.General formula: CnH2n-2 where n = # of carbon atoms
The name uses the ending -yne.The simplest alkynes are:
C2H2 Ethyne (commonly known as acetylene)
C3H4 Propyne or propylene
Aliphatic hydrocarbons: Alkynes
Ethyne
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Ball and stickmodel
Space fillingmodel
Molecular formula
Structuralformula
Representing Aliphatic Hydrocarbons
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Cycloalkanes
Carbon can also form ringed structures.
Five- and six-membered rings are most stable.They can take on conformations in which their bond angles are very close to the tetrahedral angle.
Smaller rings are quite strained
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Aromatic hydrocarbons
They have benzene ring structure ( hexagon) and have particular aroma associated with it.
CH3
Benzene Toluene ( methyl benzene)
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8 Hydrocarbons
A are polar.B are held together by ionic bonds.C contain nitrogen.D contain only hydrogen and carbon atoms.
E are held together by hydrogen bonds.
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9 Hydrocarbons containing only single bonds between the carbon atoms are called __________.
A alkenes
B alkynes
C aromatics
D alkanes
E ketones
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10 The general formula of an alkane is _______.
A C2nH2n+2
B CnH2n
C CnH2n+2
D CnH2n-2
E CnHn
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11 Which is the formula of an alkane?
A C10H10
B C10H18C C10H20
D C10H22
E C10H24
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12 The molecular geometry of each carbon aton in an alkane is ________.
A octahedral
B sqaure planar
C trigonal planar
D tetrahedral
E trigonal pyramidal
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13 Hydrocarbons containing carbon-carbon triple bonds are called________.
A alkenes
B alkynes
C aromatics
D alkanes
E ketones
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14 Which is the formula of an alkyne?
A C10H10
B C10H18C C10H20
D C10H22
E C10H24
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15An alkene has at least one ________ and has the general formula ______. A C-C single bond, CnH2n+2
B C-C double bond, CnH2n
C C-C triple bond, CnH2n
D C-C double bond, CnH2n-2
E C-C triple bond, CnH2n-2
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16 ________ could be the formula of an alkene.
A C3H8
B C3H6
C C6H6
D C17H36
E CH8
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17 Which of the following hydrocarbons has a double bond in its carbon skeleton?
A C3H8
B C2H6
C CH4
D C2H4
E C2H2
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18 The compound below is an _________.
A alkyne
B alkene
C alkane
D aromatic compound
E olefin
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19 The gasoline consumed by an automobile is a fossil fuel consisting mostly of
A aldehydes
B amino acidd
C alcohols
D hydrocarbons
E thiols
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Structural isomers
Geometric isomers
Enantiomers
Isomers
Hydrocarbons exhibit a phenomenon called isomerism- existence of different molecular arrangement but same formula
Isomers are compounds with the same molecular formula but different structures and properties.
There are 3 different types of isomers:
click here for an animationon Isomers
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Structural Isomers
Structural isomers have different covalent arrangements of their atoms.
These three compounds all have the same molecular formula, but differ in which atoms are bonded together.
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cis isomerThe two CH3 groups are on the same side.
trans isomer: The two CH3 groups are
on opposite sides.
Geometric Isomers
Geometric isomers must contain a C=C double bond.
Geometric isomers have the same covalent arrangements but differ in spatial arrangements. Geometric isomers are referred to as either cis or trans.
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Enantiomers differ in spatial arrangement around an asymmetric carbon, resulting in molecules that are mirror images, like left and right hands. The two isomers are designated the L and D isomers from the Latin for left and right (levo and dextro).
Enantiomers
Enantiomers are isomers that are mirror images of each other.
Enantiomers cannot be superimposed on each other.
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20 Structural isomers are molecules that:
A are enantiomers.B are hydrocarbons.
C have a ring structure.D are mirror images.
E differ in the covalent arrangements of their atoms.
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21 The two molecules shown are best described as
A optical isomers
B radioactive isotopes
C structural isomers
D nonradioactive isotopes
E geometric isomers
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Which of the following is true of geometric isomers?
They have variations in arrangement around a double bond.
They have an asymmetric carbon that makes them mirror images.
They have the same chemical properties.
They have different molecular formulas.
Their atoms and bonds are arranged in different sequences
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A
B
C
D
E
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Functional groups
Haloalkanes/alkenes/alkynesAlcoholsAcidsAminesKetonesAldehydesEstersEther
A functional group is an atom or group of atoms that imparts special physical and chemical properties to the compound
Based on the functional group, the compounds are classified as follows.
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Halo- alkanes/alkenes/alkynes
Haloalkanes, haloalkenes, and haloalkynes are characterized by the presence of a halogen atom (F, Cl, Br or I), in place of a hydrogen atom.
CH3Cl, CH2Cl2 , CHCl3, CCl4, CBr4, F2C=CF2 , FC = CF
They are formed when one or more H atoms are replaced by halogen atom/s.
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Alcohols
Alcohols contain the functional group -OH (hydroxyl group).
For example, in CH4, one H is replaced by -OH
The name ends with -ol, drop the alkane "e" add "ol", So, methane becomes methyl alcohol or methanol, CH3OH.
CH3CH2OH is called ethyl alcohol or ethanol.
Thiols contain the functional group -SH, (sulfhydryl group)
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Naming Alcohols
Alkaneformula Alkane name Alcohol
formulaAlcohol name
CH4 methane CH3OH methanol
C2H6 ethane C2H5OH ethanol
C3H8 propane C3H7OH propanol
C4H10 butane C4H9OH butanol
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23 Which of the following statements is true concerning a compound that contains a hydroxyl group?
A It lacks an asymmetric carbon, and it is probably a fat or lipid.
B It should dissolve in water.
C It should dissolve in a nonpolar solvent.
D It won't form hydrogen bonds with water.
E It is hydrophobic.
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24 In which of the structures are the atoms bonded ionic bonds?
A A
B B
C C
D C, D, E
E None of the structures
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Carboxylic acids
The functional group is -COOH
Replace one H atom in the alkane by a -COOH group
HCOOH = Methanoic acid or formic acidCH3COOH = Ethanoic acid or acetic acid or vinegar
CH3CH2COOH = Propanoic acid
Drop the "e" from the parent alkane and add "oic acid"
C C OH
C
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Amines
The functional group is - NH2
CH3NH2, replace one H by an -NH2 group
CH3NH2 Amino methane or Methyl amine
More than one functional groups, same or different are common in organic compounds
example: amino acids. They have amine and acid groups
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25 Which of the structures contain(s) a carboxyl group?
A A
B B
C C
D C & E
E None of the structures
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What is the name of the functional group shown in the following figure?
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AB
C
D
E
carbonyl ketone
aldehydecarboxyl hydroxyl
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Which two functional groups are always found in amino acids?
ketone and aldehydecarbonyl and carboxylcarboxyl and aminophosphate and sulfhydrylhydroxyl and aldehyde
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A
B
C
D
E
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Ketones
The functional group is -C=O or "carbonyl" groupUsually sandwiched between two carbon groups
CH3CH2CH3 = propaneCH3CO CH3 propanone or acetone ( nail polish remover)Drop e and add none
CH3COC2H5 Ethyl methyl ketone or butanone
O
H3C- C- CH3
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A function the functional group can make!
Ketones
Estrogen- has two hydroxyl groups in it.
Testosterone - one hydroxyl group is replaced by a ketone.
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Aldehydes
The functional group is -CHO with a C=O bond
drop 'e' of the parent alkane and add 'nal'
HCHO - (1 carbon) Methanal or Formaldehyde
CH3CHO- (2 carbon) Ethanal or Acetaldehyde
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Aldehydes, Ketones and AcidsThe way the carbonyl group is bonded to the main body of the
molecule is different in acids, ketones and aldehydes
The C=O is between two other carbon atoms ( alkyl groups) in the molecule
The C=O group is at the end ( terminal carbon) of the molecule and should be connected to a H atom
The C=O bond should be connected to an OH group
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What is the name of the functional group shown in the following figure?
R-C=O R
carbonyl ketone aldehyde carboxyl hydroxyl
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ABC
D
E
(R = any carbon group)
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Ester
The functional group is -COOR where R could be another alkyl group. Esters are formed by the combination of an acid and an alcohol by eliminating one molecule of water.
They are usually pleasant smelling compounds ( natural oils and essence)
CH3COOH + CH3OH --> CH3COOCH3
CH3COOCH3 methyl acetate
CH3COOC2H5 ethyl acetate
C2H5COOCH3 methyl propanoate
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EtherThe functional group is an O atom sandwiched between two carbon groups
CH3-O- CH3 dimethyl ether
They are highly flammable and used as solvents in organic synthesis
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Groups with a Carbon–Oxygen Double Bond (Carbonyl Groups)
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AmidesAmides are formed by the reaction of carboxylic acids with amines.
RCOOH + H2NR' -->
-H2O
CONH linkage is known as the amide linkage ( peptide) in proteins
This linkage is formed when several amino acids join with their acid and amino groups together.
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29 Which is the best description of a carbonyl group?
A an oxygen joined to a carbon by a single covalent bond
B a nitrogen and two hydrogens joined to a carbon by covalent bonds
C a carbon joined to two hydrogens by single covalent bonds
D a sulfur and a hydrogen joined to a carbon by covalent bonds
E a carbon atom joined to an oxygen by a double covalent bond
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30 What is the name of the functional group shown below. A carbonylB ketoneC aldehydeD carboxylE hydroxyl
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31 Which of the following contains nitrogen in addition to carbon, oxygen, and hydrogen?
A an alcohol such as ethanolB a monosaccharide such as glucoseC a steroid such as testosteroneD an amino acid such as glycineE a hydrocarbon such as benzene
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32 What type of functional group is shown in the compound below?
A carbonylB ketoneC aldehydeD carboxylE hydroxyl
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33 Which molecule contains an amine functional group?
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34 Which molecule contains an aldehyde functional group?
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35 Which molecule contains an alcohol functional group?
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36 Which one of the following is not an alcohol?
A acetone
B glycerol
C ethanol
D cholesterol
E ethylene glycol
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Macromolecules
Macromolecules are large molecules composed of smaller molecules.
They are complex in their structures.
Carbon has the unique property of joining together via covalent bonding to form large (macro) molecules. Most macromolecules are polymers, built from monomers.
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Macromolecules
Three of the classes of life’s organic molecules are polymers:
There are some macromolecules that are not polymers:
lipidsphospholipidssteroids
ProteinsCarbohydratesNucleic acids
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Although organisms share the same limited number of monomer types, each organism is unique based on the arrangement of monomers into polymers
An immense variety of polymers can be built from a small set of monomers
Polymers
Polymer Made of these monomers
Proteins Amino acids Carbohydrates Simple sugars (monosaccharides)
Nucleic acids Nucleotides
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Monomers form larger molecules by condensation reactions called dehydration reactions
Polymers
Is a long molecule consisting of many similar building blocks called monomers
longer polymer
Monomershort polymer
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Amino Acids and Proteins
Proteins are formed when several amino acids combine together
Acid and amine end of the molecules join together to form long peptide chain
Peptide chain with 50 or more amino acids can form an individual protein.
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Carbohydrates (sugars)Simple sugars are poly-hydroxy aldehydes or ketones.
Table sugar, (sucrose) is made up of glucose and fructose.
They all have several hydroxyl groups in their structure that makes them soluble in water.
C
glucose fructose
(monosaccharide)
Glucose and fructose are monosaccharides.
Sucrose is a disaccharide.
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In solution, they form cyclic structures.
These can form chains of sugars that form structural molecules such as starch and cellulose.
Carbohydrates (sugars)
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Nucleic Acids
Nucleic acids are made up of monomer units called nucleotides
Sugar + Base + PO43- = nucleotide
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Two of the building blocks of RNA and DNA are sugars (ribose or deoxyribose)
and cyclic bases (adenine, guanine, cytosine, and thymine or uracil)
Nucleic AcidsSlide 80 / 97
RNA DNA
carry genetic code
A, C, G and T
deoxyribose
Deoxyribonucleic acid
make proteins
A, C, G and U
ribose
Ribonucleic acidAcid
Sugar
Bases
Function
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Nucleotides combine to form the familiar double-helix form of the nucleic acids
The blue ribbon is the sugar/phosphate backbone
The bases are the rungs in the (spiral) ladder
The nucleotides join together via hydrogen bonding through their basesA-T, C-G etc.
Nucleic Acids
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37 Which of the following is not one of the four major groups of macromolecules found in living organisms?
A glucoseB carbohydratesC lipidsD proteinsE nucleic acids
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38 Glucose is a type of _______.
A amino acidB proteinC carbohydrateD nucleotideE nucleic acids
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39 Nucleic acids are made up of __________.
A amino acidsB proteinsC carbohydratesD nucleotidesE sugars
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40 A nucleotide consists of _____________.
A glucose + fructose + amino acidB glucose + fructose + phosphate groupC amino acid + protein + phosphate group D sugar + base + amino acidE sugar + base + phosphate group
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41 Polymers of polysaccharides and proteins are all synthesized from monomers by which process?
A connecting monosaccharides together (condensation reactions)
B the addition of water to each monomer (hydrolysis)C the removal of water (dehydration reactions)D ionic bonding of the monomers
E the formation of disulfide bridges between monomers
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Other complex molecules of lifeFats and Lipids
Are a diverse group of hydrophobic molecules
Are the one class of large biological molecules that do not consist of polymers
Share the common trait of being hydrophobic
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FatsAre constructed from two types of smaller molecules, a single glycerol and usually three fatty acids
Fatty acidsCarboxylic acids with a very long chain of carbon atoms.Vary in the length and number and locations of double bonds they contain
Fats and Fatty Acids
a fatty acid
CH2OH
CH2OH
CH2OH
glycerol
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Dehydration Synthesis
The attachment of a fatty acid to glycerol results in a removal of a water molecule.
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The diagram shows three fatty acids added to glycerol producing a fat molecule.
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Saturated fatty acidsHave the maximum number of
hydrogen atoms possible
Have no double bonds in their carbon chain
Mainly animal origin
Unsaturated fatty acidsHave one or more double bonds
When hydrogenated ( add more Hydrogen) they become solid and saturated
Mainly plant origin
Saturated and Unsaturated Fatty Acids
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Have only two fatty acids
Have a phosphate group instead of a third fatty acid
Results in a bilayer arrangement found in cell membranes
Phospholipids
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Are lipids characterized by a carbon skeleton consisting of three or more fused rings
cholesterol
Steroids
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42 Which of the following is (are) true for the class of large biological molecules known as lipids?
A They are insoluble in water.B They are an important constituent of cell membranes.
C They provide the least amount of energy in living organisms
D Only A and B are correct.E A, B, and C are correct.
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43 Saturated fatty acids A are the predominant fatty acid in corn oil.
B have double bonds between carbon atoms of the fatty acids.
C have a higher ratio of hydrogen to carbon than do unsaturated fatty acids.
D are usually liquid at room temperature.
E are usually produced by plants.
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44 The hydrogenation of vegetable oil would result in which of the following? A a decrease in the number of carbon-carbon
double bonds in the oil (fat) molecules
B an increase in the number of hydrogen atoms in the oil (fat) molecule
C the oil (fat) being a solid at room temperature
D A and C only
E A, B, and C
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