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Chem 106 quiz 1
chapter 10-16 gen, organic, bio chemistry
73
Biochemistry
Undergraduate 1
02/21/2012

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Term
What do C-C single bonds allow? Majorly found in which class of hydrocarbon?
Definition
Free rotation; Alkanes
Term
Cycloalkane
Definition
2 less hydrogens than alkanes
simplest: cyclopropane
shapes
CnH2n + 2 rule
Term
Isomers
Definition
When two compounds have the same molecular formula but C atoms bonded in a different order
Term
alkyl group
Definition
an alkane that is missing on hydrogen atom
ex: methyl CH3
Term
Functional Groups
Definition
-C atoms most likely to bond with nonmetals: H, N, O, S, P and halogens
-classify organic compounds according to their structure
-chemical rxns
-found in biomolecules: proteins, lipids, carbs
Term
What type of hydrocarbons are alkenes and alkynes?
Definition
Unsaturated. due to double and triple bonds
Term
What type of hydrocarbons are alkanes?
Definition
Saturated. MAX number of hydrogens possible
Term
Ionic Bond
Definition
Attraction between oppositely charged ions, loss and gain of electrons.
complete transfer of electrons
Term
Aromatic
Definition
Compound containing BENZENE, a molecule that has a ring of 6 carbon atoms with 1 H attached to each C
-picture: hexagon with circle in ctr.
-cyclic and contains double bonds
Term
Nucleophilic Functional Groups
Definition
Alcohols, Amine or Amino groups, & Thiols (sulfhydryls)
-electron rich
-lone pair of electrons
-partial negative charge (anions)
Term
Alcohols
Definition
Hydroxyl or -OH bonded to (a C atom)
-can ionize or deprotenate (in water based solutions):loss of a proton or H+
--ex: CH2OH --> CH30 neg. chrg + H+ pos. chrg
--O becomes more nucleophilic from deprotenation
-attacking species
-
Term
What does "R" represent?
Definition
Hydrogens and carbons
Term
What do curved arrows symbolize?
Definition
The direction of electron flow;
movmt of electron pair
Term
Classifications of the Alcohols
Definition
Primary, Secondary and tertiary
-1: attached to zero or 1 other C; 1 alkyl group
-2: attached to 2 alkyl groups
-3:3 alkyl groups
Term
Good Leaving Groups
Definition
Takes electrons and goes basically anything electronegative can leave Cl, Br, I, At (Halides) -OR, -SR -OH?, -OH2?,
Term
What does the oxidation of a primary alcohol produce?
Definition
An aldehyde. (contains a double bond between C & O).
Ex: oxidized Methanol (Takes a H from -OH and H around C)
Term
How do aldehydes oxidize and what is then the final product?
Definition
They need added Oxygen; final product is carboxylic acid

-ex: acetaldehyde --> acetic acid
Term
Bad leaving groups
Definition
H
R group(C)
Term
Oxidation of Functional Group
Definition
increase in C-O bonds
loss of electrons
loss H atoms or addition of O
gain of C=C bonds (from C-OH bond)
Term
Oxidizing Agent
Definition
Oxidizing something and therefore is reduced
Term
Reduction
Definition
decrease C-O bonds
gain of electrons
Term
Amine or Amino Group
Definition
NH2 or R-NH2
central atom is a Nitrogen atom; derivative of ammonia (NH3)in which C atoms replace one, two, or three of the hydrogen atoms
Term
Thiols
Definition
a.k.a SULFHYDRYLS
the functional grp -SH is bonded to a C atom
similar, but slightly less neg. than -OH
Term
What happens if there are 2 thiols in a solution? What is the product important in?
Definition
They will deprotenate, the thiols will join, and they will create a disulfide.
Important in proteins (offer stability).
Term
Electrophilic Groups
Definition
(1)Carboxylic acids, (2)Aldehydes, (3)Ketones, (4)Esters, (5)Amides, (6)Phosphate esters
-electron deficient
-attacked by nucleophiles
-may have partial positive chrg
Term
Carboxylic Acid
Definition
the functional group is a combo of the carbonyl and hydroxyl groups. the first C atom is part of a carboxyl group
R-COOH(ex:CH3COOH)
O=C : carbonyl
R= alkane (hydrocarbon)
*Will always be attacked (bc an electrophil)
Term
Aldehyde
Definition
first C of carbon chain is a carbonyl group that is bonded to a H atom
(RCHO)
- can oxidize by adding [O] to make carboxylic acid
exs p. 8 notebook
Term
What is the simplest aldehyde?
Definition
Formaldehyde
HCHO
only aldehyde that has carbonyl grp attached to 2 H atoms
Term
Ketone
Definition
carbonyl group is bonded to 2 other C atoms
RCOR
exs p. 8 notebook
Term
Ester
Definition
similar to carboxylic acid,except the oxygen of the carbonyl group is attached to a C and not a hydrogen
(O=COC v. O=COH)
Made from carboxylic acids and alcohols
Term
The reactants carboxylic acid plus alcohol makes what two products?
Definition
ester and water
Term
Amide
Definition
hydroxyl group of a carboxylic acid is replaced by a nitrogen group
RC=O-NH2
p. 9
Made from carboxylic acids & amines
Term
Phosphate Esters
Definition
ester bonds form between hydroxyl group of an alcohol and phosphoric acid
O=POR
Term
Phosphoric Acid
Definition
HOP=OOHOH -Strong acid due to 3 OH's -good leaving groups on electrophiles
Term
The reactants phosphoric acid and alcohol make what?
Definition
Phosphate ester and water
Term
The reactants phosphate ester and alcohol form what?
Definition
Phosphate diester + Water p.621
Term
What do the reactants carboxylic acid and amine produce?
Definition
Amide and Water
p.8
Term
Nucleophiles
Definition
Translation: Nucleus-loving
• Chemical meaning: Reacts with positivelycharged (or partially positive) atoms
(electrophiles: electron-loving)
• Characteristics: Nucleophilic atoms will
have either lone pairs or pi bonds that can
be used to form new bonds to electrophiles
-the attacker
Term
Electrophiles
Definition
Translation: Electron-loving
• Chemical meaning: Reacts with sources of
electrons (nucleophiles: nucleus-loving)
• Characteristics: Electrophilic atoms will have
– Positive charge, a partial positive charge, or be very
polarizable
– An empty orbital or a heterolytically breakable bond
(to a leaving group
-gets attacked
Term
Alkanes: states of matter
Definition
C1 through C4 = gases (naturally)
C5-C17 = liquids, oils, gasoline (jet fuels, high b.p)
C18 and higher = solids
-In general, soluble in water
-lowest m.p.&b.p. of all hydrocarbons (compared to biomolecules)
Term
Combustion
(alkanes)
Definition
-Alkanes mix with oxygen to make CO2 with H2O and Energy
-propane, gasoline, etc
-(be able to draw it)
-cellular/physiological ex on p.10
Term
Know Electron Dot Structures & Name of molecular formulas
Definition
exs p. 10
Term
Alkanes
Definition
-atoms connected by single bonds
-H's saturate C's
-90% of biosphere made up of organic matter
-stabilized by Van Der Waals interactions
Term
Alkenes
Definition
-double bonds
-bond angles = 120 degrees
-have fewer hydrogens, replaced by C=C
-
Term
What is the simplest Alkene?
Definition
Ethene C2H4
Term
C=C bonds
Definition
Rigid, cannot rotate
in alkenes
Term
Geometric Isomers
Definition
Cis- 2 large groups, usually alkyl groups or halogen atoms are on same side of the double bond
Trans- lg. groups on opposite sides of the double bond farther apart than cis are = MORE STABILITY
Term
Physical Properties of Alkenes
Definition
-similar to alkanes
-Halogenation of Alkenes- addition rxn
(hydrogenation = adding H's
(ex p.10)
Term
Cis-Trans Notation
Definition
Steps: find longest C chain
Replace -ane with -ene
Term
Alkynes
Definition
-hydrocarbons with more unsaturation, triple bonds
-bond angles 180 degrees
-very useful
-anti tumor producing agents
-do not have cis-trans because the C's in the triple bond are each attached to only one group
Term
Optical Isomers
Definition
-identical molecules but mirror images
-aka Enantiomers
-have same atoms but arranged differently in space
-Not superimposable
ex: hands - can't fit a R glove on L hand; can't have palm of L&R face up and have everything aligned, doesn't work!
CHIRAL- Molecule where carbon center has four different* molecules or groups attached
Term
Biomolecules
Definition
Proteins
Sugars/carbs
fatty acids
nucleic acids
Term
Proteins
Definition
-made up of A.A.
-AA has carboxylic acid group, amine group, R group (20 different), has chiral attached to it NCHRC
--> therefore, optical isomers in AA
Term
Sugars/Carbohydrates
Definition
-made up of polyhydroxyl (C-OH)Aldehyde and Ketones
ALDOSE-carbonyl group is on the first C (-CHO)
KETOSE-carbonyl group on the second carbon atom as a ketone (c=O)
Term
Fatty Acids
Definition
-Carboxylic Acids & hydrocarbons
-Make up lipids
-Found in membranes
more info?
-A lot more Energy harnessed from fats than from sugar
Term
Nucleic Acids
Definition
-building blocks of DNA/RNA
-nucleotidetriphosphate, ""diphosphate, monophosphate
-purines: Adenine & Guanine
-pyrimidines:Cytosine, Uracil, Thymine
-amide: O=C-N
Term
What do acids donate?
Definition
Protons
Term
WATER
Definition
-biomolecules are influenced by solvation of H2O
-most abundant biomolecule (60-90%) cellular
-most unusual properties
- high heat of vaporization, surface tension and b.p/m.p.
Term
Hydrogen Bonding
Definition
Mutual attraction of H2O to itself
the WEAK electrostatic interaction between a H attached to an electronegative atom and its interaction with another electronegative atom
-no equal sharing of electrons in water (parital negative & partial positive)
-easy to break
Term
Water's 4 Major Types of Non-Covalent Forces
Definition
1) charge-charge interactions
2) Hydrogen bonding
3) Vander Waals forces
4) Hydrophobic interactions
Term
How do you draw Hydrogen bonding?
Definition
Draw here. (p.16)
Term
How many water molecules can one water bond to?
Definition
Four.
Term
How do you draw a Hydrogen bond between one molecule and a ketone?
Definition
Draw here. (p.16)
Term
Draw H bond between H2O and an Amine.
Definition
Draw here (p. 16)
Term
Why does ice float?
Definition
-In liquid water, the molecules are packed closer together & therefore more dense. Upon freezing, the molecules form a less dense (max H bonds) lattice structure & therefore floats to surface.
-hexagonal lattice structure
-every molecule is H bonded to 4 others
Term
Solvent Properties of H2O
Definition
-good solvent to polar molecules
functional groups that would be
polar: Amide, alcohol, carboxylic
acid, aldehyde, ketones, etc)
-good solvent to ionic molecules
ex: Table salt Na plus, Cl minus
-Poor solvent for Hydrocarbons (b/c hydrocarbons have covalent bonds & water is polar)
Term
Solvation Rule
Definition
"like dissolves like"
-Hydrophobic = water hating
-Hydrophilic = water loving
ex: water will dissolve with Carbox. acid, alcohol, etc
Term
Partitioning
Definition
Hydrophilic biomolecules will mix with water, hydrophobic will separate
- Benzene ---> alkene;subsides in oil layer
- Urea ---> polar; subsides in water
- NaCl ---> polar; subside in water
- Vitamin A ---> Amphipathic = both layers. polar head, phobic tail
Term
SODIUM DODECYL SULFATE (SDS)
Definition
draw here. p. 18
Term
Hydrophobic Bonding
Definition
-anterior of micell
-noncovalent bonding with the exclusion of water
**very important for protein stability
-In protein, phobi inside, philic outside, water pushed out (doesn't want + chrg inside protein)
Term
Charge to Charge interactions
Definition
-strongest of noncovalent interacts
-longest distance out of 4 noncovalent forces (dist. is important)
-SALT BRIDGE- 2 AA of opposite chrg interior of protein
Term
Van der Waals
Definition
-weakEST electrostatics
-short range
-C=O all in proteins
Term
What are the structural isomaers for all 10 alkanes?
Definition
meth, eth, prop = 1
but = 2
pent = 3
hex = 5
Hept = 9
oct = 18
Non = 35
dec= 75
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