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OCHEM 2 Test 4
OCHEM 2 Test 4
299
Organic Chemistry
Undergraduate 2
11/17/2019

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Cards

Term
What's number 1?
[image]
Definition
aldopentose
Term
What's number 2
[image]
Definition
ketohexose
Term
What's number 3?
[image]
Definition
D-aldopentose
Term
What's number 4?
[image]
Definition
D-ketopentose
Term
What's number 5?
[image]
Definition
β-D-pentopyranose
Term
What's number 6?
[image]
Definition
anomeric -OH
Term
What's number 7?
[image]
Definition
anomeric C
Term
What's number 8?
[image]
Definition
anomeric H
Term
What's number 9?
[image]
Definition
α-D-aldopentofuranose
Term
What's number 10?
[image]
Definition
β-D-aldohexopyranose
Term
What's number 11?
[image]
Definition
D-fructose
Term
What's number 12?
[image]
Definition
D-glucose
Term
What's number 13?
[image]
Definition
α,D-fructofuranose
Term
What's number 14?
[image]
Definition
D-ribose
Term
What's number 15?
[image]
Definition
α,D-ribopyranose
Term
how aldoses become cyclized
Definition
[image]
Term
how aldose as a hemiacetal gets converted to acetal
Definition
[image]
Term
what's number 1?
[image]
Definition
starch
1'4'-α link
Term
what's number 2?
[image]
Definition
maltose
1',4'-α link
Term
what's number 3?
[image]
Definition
lactose
1',4'-β link
Term
what's number 4?
[image]
Definition
cellobiose
1',4'-β link
Term
what's number 5?
[image]
Definition
cellulose
1',4'-β link
Term
what's number 6?
[image]
Definition
sucrose
1'α,2'β link
Term
what's number 7?
[image]
Definition
type O
Term
what's number 8?
[image]
Definition
type A
Term
what's number 9?
[image]
Definition
type B
Term
is starch easily hydrolized?
Definition
yes
Term
an example of carbohydrates being used to distinguish self from non-self
Definition
blood types
Term
is cellulose easily hydrolized?
Definition
no
Term
most prevalent disaccharide in nature
Definition
sucrose
Term
a characteristic of sucrose that's rare among disaccharides
Definition
linkage at anomeric O
Term
primary natural products
Definition
ubiquitous; found everywhere
Term
secondary natural products
Definition
more species specific
Term
the formula for carbohydrates
Definition
Cx(H2O)y
Term
what carbohydrates essentially are
Definition
polyhydroxy aldehydes and ketones
Term
the suffix used for carbohydrates
Definition
-ose
Term
the carbon that always has the keto group in a ketose
Definition
C2
Term
what the anomeric C in a carbohydrate does
Definition
everything an aldehyde would do
Term
major functions of carbohydrates
Definition
-energy storage
-structural (supportive tissue)
Term
[image]
Definition
chitin
Term
almost all amino acids are (α or β)
Definition
α
Term
the types of R groups that can exist on amino acids
Definition
-nonpolar
-polar
-basic
-acidic
-aromatic
Term
can humans make aromatic rings?
Definition
for the most part, no, so most amino acids with phenyl group are essential
Term
what is this?
[image]
Definition
a peptide bond in an amino acid chain
Term
some functions of proteins
Definition
-enzymes, catalyst, amylase
Term
the most abundant organic compounds in nature
Definition
carbohydrates
Term
the reaction of photosynthesis
Definition
[image]
Term
Most living organisms oxidize glucose to carbon dioxide and water to provide the
energy needed by their cells. Even plants do this with the starch they produce.
Definition
Term
glycogen
Definition
a form of starch found in animals
Term
the modern definition of carbohydrate
Definition
includes polyhydroxyaldehydes,
polyhydroxyketones, and compounds that are easily hydrolyzed to them.
Term
examples of hydrolysis of disaccharides and polysaccharides
Definition
[image]
Term
criteria by which monosaccharides are classified
Definition
1. The number of carbon atoms in the carbon chain
2. Whether the sugar contains a ketone or an aldehyde group
3. The stereochemical configuration of the asymmetric carbon atom farthest from
the carbonyl group
Term
aldoses
Definition
sugars with aldehyde groups
Term
ketoses
Definition
sugars with ketone groups

the ketone group is usually at C2
Term
most naturally occurring sugars are (D or L)
Definition
D
Term
epimers
Definition
Sugars that differ only by the stereochemistry at a single
carbon
Term
An aldehyde reacts with one molecule
of an alcohol to give a hemiacetal, and with a second molecule of the alcohol to
give an acetal.
Definition
Term
most hemiacetals decompose spontaneously to the aldehyde and the alcohol because...
Definition
the hemiacetal is not as stable as the acetal
Term
why hemiacetals are rarely isolated
Definition
because the hemiacetal is not as stable as the acetal, and most hemiacetals
decompose spontaneously to the aldehyde and the alcohol
Term
mechanism for formation of a cyclic hemiacetal
Definition
[image]
Term
how a straight-chain carbohydrate turns into a ring
Definition
[image]
Term
what's number 1?
[image]
Definition
glucose
Term
what's number 2?
[image]
Definition
fructose
Term
what's number 3?
[image]
Definition
an aldohexose
Term
what's number 4?
[image]
Definition
a ketohexose
Term
what's number 5?
[image]
Definition
an aldotetrose
Term
what's number 6?
[image]
Definition
a ketotetrose
Term
aconitase mechanism
Definition
[image]

this is an E2 mechanism
Term
what enzymes do for the chemicals involved in rxns
Definition
make collisions more effective
Term
hemiketal
Definition
cyclic hemiacetal of a ketone
Term
how a ketohexose goes from straight-chain to cyclic form
Definition
[image]
Term
what's number 1?
[image]
Definition
pyran
Term
what's number 2?
[image]
Definition
a pyranose
Term
what's number 3?
[image]
Definition
furan
Term
what's number 4?
[image]
Definition
a furanose
Term
α anomer of a carbohydrate
Definition
the anomer with the anomeric -OH pointing down
Term
β anomer of a carbohydrate
Definition
the anomer with the anomeric -OH pointing up
Term
glycoside
Definition
carbohydrate where the H on the anomeric -OH has been replaced by an R group
[image]
Term
what's number 1?
[image]
Definition
α glycosidic bond
Term
what's number 2?
[image]
Definition
methyl α-D-glucopyranoside
Term
what's number 3?
[image]
Definition
β glycosidic bond
Term
what's number 4?
[image]
Definition
methyl β-D-glucopyranoside
Term
the types of R groups that exist on amino acids
Definition
-nonpolar
-polar
-basic
-acidic
-aromatic
Term
for the most part, humans can't make aromatic rings, so most AA's with phenyl groups are essential
Definition
Term
some functions of proteins
Definition
-enzymes
-structure
-transport
-hormones
Term
examples of proteins being enzymes
Definition
-lysozyme
-amylase
-many others
Term
each rxn in the cell has a specific enzyme dedicated to it.
Definition
Term
some examples of proteins functioning in structure
Definition
-α-keratin
-collagen
-myosin
-actin
Term
some examples of proteins functioning in transport
Definition
-hemoglobin
-cytochrome C
-antibodies
Term
hemoglobin
Definition
-transports O2 -4 myoglobin subunits put together
Term
cytochrome C
Definition
transports electrons
Term
some examples of proteins functioning as hormones
Definition
-insulin
-HGH
Term
the role of hormones
Definition
helps regulate massive areas of metabolism
Term
not all hormones are proteins
Definition
Term
primary structure of proteins
Definition
sequence of AA's from C to N terminus
Term
AA sequence determines all the functions of a protein
Definition
Term
types of secondary structure in proteins
Definition
-α-helix
[image]
-β-sheet
[image]
-random coil
Term
random coil
Definition
part of polypeptide chain with no orderly secondary structure at all

example: segments of α helix or pleated sheet separated by kinks of random coil
Term
tertiary structure
Definition
how the secondary features relate to each other
its complete three-dimensional conformation
Term
quarternary structure
Definition
subunits coming together

association of two or more peptide chains in the complete protein

not in all proteins
Term
bringing -SH groups on cysteine together can cause oxidation such that a disulfide bridge forms
Definition
Term
hemoglobin made of 4 myoglobins
Definition
Term
2 major categories of secondary natural products
Definition
-water soluble
-water insoluble
Term
types of water insoluble secondary natural products
Definition
-lipids
-fatty acids
Term
types of lipids
Definition
-saponifiable
-non-saponifiable
Term
saponification
Definition
[image]
Term
[image]
Definition
fatty acid

R group contains 12-50 C's
Term
lipids that are saponifiable
Definition
esters
Term
lipids that are non-saponifiable
Definition
those that are not esters
Term
types of fatty acids
Definition
-saturated
-unsaturated
Term
saturated fatty acids come from ______.
unsaturated fatty acids come from ______.
Definition
animals
plants
Term
where the alkene group is in an unsaturated fatty acid
Definition
in the middle of the hydrocarbon chain
[image]
Term
lipids
Definition
secondary natural products that don't dissolve in water
Term
functions of lipids
Definition
-fuel
-membrane components
-hormones
Term
lipids have significantly more energy per gram than carbohydrates, but carbohydrates provide faster fuel
Definition
Term
[image]
Definition
wax
Term
coenzymes
Definition
they help enzymes carry out their function
Term
Claisen synthesis of thioesters
Definition
[image]
Term
waxes tend to be the hardest lipids to saponify because it's hard to get the aqueous solvent to make the huge -OR group leave
Definition
Term
functions of waxes
Definition
-protective
-structure
-coating wool
Term
examples of wax being protective
Definition
-fruit surfaces
-wax on car
-coating wool and feathers to keep it dry
Term
examples of wax functioning in structure
Definition
-bee's wax
-making sperm whale more hydrodynamic (no barnacles on front end)
Term
waxes tend to have -OR groups containing 20 or more C's
Definition
Term
[image]
Definition
triglyceride
Term
are double bonds in the R group of triglycerides cis or trans?
Definition
cis
Term
unsaturated fats easier to digest because there's more functional groups for the enzymes to act on
Definition
Term
unsat fats become rancid when left alone (rxns with light and leftover food particles)
Definition
Term
how unsaturated triglycerides are hydrogenated
Definition
[image]
Term
basic structure of a phospholipid
Definition
[image]
Term
the 3 general structures phospholipids can have in a cell membrane
Definition
[image]

the ratio of these depends on the context of each cell (temperature of environment and such)
Term
[image]
Definition
Term
the basic structure of an α-amino acid
Definition
[image]
Term
what is this?
[image]
Definition
peptide bonds
Term
the R and S configuration of an amino acid does not imply optical rotation ((+) or (-))
Definition
Term
complete proteins
Definition
Proteins that provide all the essential amino acids in about the right proportions
for human nutrition
Term
incomplete proteins
Definition
Proteins that are severely deficient in one or more of the essential amino acids
Term
rare amino acids
Definition
amino acids found in smaller quantities than standard amino acids

however, they are commonly found in collagen
Term
the acidic part of an amino acid molecule
Definition
-NH3+
Term
the basic part of an amino acid
Definition
-COO-
Term
acidity and basicity of an amino acid compared to that of carboxylic acid and amine
Definition
[image]
Term
protonation and deprotonation of an amino acid in response to change in pH
Definition
[image]
Term
titration curve for an amino acid, in this case, glycine
Definition
[image]
Term
isoelectric pH AKA isoelectric point,
abbreviated pI
Definition
the pH at which the amino acid has a neutral overall charge
Term
[image]
Definition
Term
[image]
Definition
Term
how a peptide bond is formed
Definition
[image]
Term
how a disulfide bridge is formed
Definition
[image]
[image]
often occurs between cysteines
Term
[image]
Definition
Term
Simple proteins
Definition
proteins that hydrolyze to give only amino acids
Term
Conjugated proteins
Definition
proteins bonded to a nonprotein prosthetic group such as a sugar, a nucleic acid, a lipid, or some other group
Term
some classes of conjugated proteins
Definition
-glycoproteins
-nucleoproteins
-lipoproteins
-metalloproteins
Term
Fibrous proteins
Definition
stringy, tough, and usually insoluble in water

They function primarily as structural parts of the organism
Term
primary function of fibrous proteins
Definition
They function primarily as structural parts of the organism
Term
globular proteins
Definition
proteins folded into roughly spherical shapes

They usually function as enzymes, hormones, or transport proteins
Term
function of globular proteins
Definition
usually function as enzymes, hormones, or transport proteins
Term
enzymes
Definition
protein-containing biological catalysts
Term
the role of hormones
Definition
they help to regulate processes in the body

example: insulin regulates glucose levels in the blood and its uptake by cells
Term
Transport proteins
Definition
they bind to specific molecules and transport them in the blood or through the cell membrane

example: hemoglobin
Term
Lipids
Definition
substances that can be extracted from cells and tissues by nonpolar organic solvents
Term
Lipids are classified by...
Definition
their solubility
Term
Complex lipids
Definition
those that are easily hydrolyzed to simpler constituents
Term
Most complex lipids are...
Definition
fatty acids
Term
fatty acids
Definition
esters of long-chain carboxylic acids
Term
the 2 groups of fatty acids
Definition
-waxes
-glycerides
Term
Waxes
Definition
esters of long-chain alcohols
Term
glycerides
Definition
esters of glycerol
Term
Simple lipids
Definition
those that are not easily hydrolyzed by aqueous acid or base
Term
three important groups of simple lipids
Definition
-steroids
-prostaglandins
-terpenes
Term
[image]
it seems complex lipids are saponifiable and simple lipids are non-saponifiable
Definition
Term
Waxes
Definition
esters of long-chain fatty acids with long-chain alcohols
Term
general structure of waxes
Definition
[image]
Term
Glycerides
Definition
fatty acid esters of the triol glycerol
Term
fats
Definition
triglycerides that are solid at room temperature
Term
oils
Definition
triglycerides that are liquid at room temperature
Term
general structure of triglycerides
Definition
[image]

triglycerides are often mixtures of fatty acids
Term
transesterification
Definition
[image]
Term
Saponification
Definition
base-promoted hydrolysis of the ester linkages in fats and oils
Term
example of how saponification is used to make soap
Definition
[image]
Term
soap
Definition
the sodium or potassium salt of a fatty acid
Term
micelles
Definition
clusters of about 100 to 200 soap molecules with their polar “heads” (the carboxylate groups) on the surface of the cluster and their hydrophobic “tails” (the hydrocarbon chains) enclosed within

[image]
Term
emulsion
Definition
mixture of two insoluble phases (grease and water), with one phase dispersed throughout the other in small droplets
Term
how soap emulsifies grease
Definition
[image]
Term
Phospholipids
Definition
lipids that contain groups derived from phosphoric acid
Term
general structure of a phospholipid
Definition
[image]
Term
Steroids
Definition
compounds whose structures are based on the tetracyclic androstane ring system
Term
some types of steroids
Definition
-hormones
-emulsifiers
-components of membranes
Term
basic structure of a steroid
Definition
[image]
Term
Prostaglandins
Definition
fatty acid derivatives that are even more powerful biochemical regulators than steroids
Term
some body systems affected by prostaglandins
Definition
-nervous system
-smooth muscle
-blood
-reproductive system
Term
some functions regulated by prostaglandins
Definition
-blood pressure
-blood clotting
-the allergic inflammatory response
-activity of the digestive system
-the onset of labor
Term
basic structure of a prostaglandin
Definition
[image]
Term
how prostaglandins are synthesized
Definition
[image]
Term
Terpenes
Definition
a diverse family of compounds with carbon skeletons composed of five-carbon isopentyl (isoprene) units
Term
some examples of terpenes
Definition
[image]
Term
[image]
Definition
isoprene (top)

isoprene unit (bottom)
Term
examples of terpenes made of isoprene units
Definition
[image]
Term
some terpenes with functional groups
Definition
[image]
Term
classification of terpenes
Definition
[image]
Term
terpenoids
Definition
A family of compounds including both terpenes and compounds of terpene origin whose carbon skeletons have been altered or rearranged
Term
Nucleic acids
Definition
substituted polymers of the aldopentose ribose that carry an organism’s genetic information
Term
what's more easily hydrolyzed and broken down? DNA or RNA?
Definition
RNA
Term
the structure of the ribose-phosphate backbone of RNA
Definition
[image]
[image]
Term
Nucleic acids are assembled on a backbone made up of ribofuranoside units linked by phosphate esters.
Definition
Term
glycoside
Definition
A cyclic acetal form of a sugar
-they are generally furanosides (five-membered) or pyranosides (six-membered)
-they exist in anomeric α and β forms
Term
aglycone
Definition
A nonsugar residue bonded to the anomeric carbon of a glycoside (the acetal form of a sugar).
-often bonded to the sugar through oxygen or nitrogen
Term
Ribonucleoside
Definition
a β-D-ribofuranoside (a β-glucosidase of D-ribofuranose) whose aglycone is a heterocyclic nitrogen base
Term
what's number 1?
[image]
Definition
D-ribose
Term
what's number 2?
[image]
Definition
β-D-ribofuranose
Term
what's number 3?
[image]
Definition
a ribonucleoside
Term
what's number 4?
[image]
Definition
pyrimidine
Term
what's number 5?
[image]
Definition
cytosine (C)
Term
what's number 6?
[image]
Definition
uracil (U)
Term
what's number 7?
[image]
Definition
adenine (A)
Term
what's number 8?
[image]
Definition
guanine (G)
Term
what's number 9?
[image]
Definition
purine
Term
The four common ribonucleosides in RNA
Definition
-cytidine
-uridine
-adenosine
-guanosine
Term
what's number 1?
[image]
Definition
cytidine (C)
Term
what's number 2?
[image]
Definition
uridine (U)
Term
what's number 3?
[image]
Definition
adenosine (A)
Term
what's number 4?
[image]
Definition
guanosine (G)
Term
ribonucleotide
Definition
ribonucleoside that is phosphorylated at its 5′ carbon

(“tied” to phosphate)
Term
what's number 1?
[image]
Definition
cytidine monophosphate,
CMP (cytidylic acid)
Term
what's number 2?
[image]
Definition
uridine monophosphate,
UMP (uridylic acid)
Term
what's number 3?
[image]
Definition
adenosine monophosphate,
AMP (adenylic acid)
Term
what's number 4?
[image]
Definition
guanosine monophosphate,
GMP (guanidylic acid)
Term
how RNA bases are joined together
Definition
[image]
Term
what's number 1?
[image]
Definition
3'-hydroxy
Term
what's number 2?
[image]
Definition
5'-phosphate
Term
what's number 1?
[image]
Definition
D-2-deoxyribose
Term
what's number 2?
[image]
Definition
β-D-2-deoxyribofuranose
Term
what's number 3?
[image]
Definition
a deoxyribonucleoside
Term
what's number 4?
[image]
Definition
cytosine (C)
Term
what's number 5?
[image]
Definition
thymine (T)
Term
what's number 6?
[image]
Definition
adenine (A)
Term
what's number 7?
[image]
Definition
guanine (G)
Term
The sequence of nucleotides is called the primary structure of the DNA strand.
Definition
Term
what's number 1?
[image]
Definition
deoxycytidine
Term
what's number 2?
[image]
Definition
deoxythymidine
Term
what's number 3?
[image]
Definition
deoxyadenosine
Term
what's number 4?
[image]
Definition
deoxyguanosine
Term
[image]
Definition
Term
how DNA bases are arranged and paired
Definition
[image]
[image]
Term
function of cyclic AMP (cAMP)
[image]
Definition
it is involved in transmitting and amplifying the chemical signals of other hormones
Term
function of Nicotinamide adenine dinucleotide (NAD)
[image]
Definition
it is one of the principal oxidation–reduction reagents in biological systems
[image]
Term
the hydrolysis of ATP
Definition
[image]

this is highly exothermic largely due to the heats of hydration of the products
Term
some examples of steroids
Definition
[image]
Term
structure of prostaglandins
Definition
[image]
Term
structure of detergents
Definition
[image]
Term
some examples of terpenes
Definition
[image]
Term
how soaps are made
Definition
[image]
Term
humectant
Definition
something that retains or preserves moisture; opposite of desiccant

soap is a humectant
Term
some cations that can interact with soap to form hard water
Definition
-Mg
-Fe
-Co
-some other cations
Term
detergent remains water soluble
Definition
Term
non-saponifiable lipids
Definition
water-insoluble secondary natural products that aren't esters
Term
basic structure of steroids
Definition
[image]
Term
some functions of steroids
Definition
-membrane components
-hormones
Term
the roles of cholesterol
Definition
-membrane component in animals
-helps membranes maintain certain fluidity and therefore flexibility
-starting material for all steroids
Term
[image]
Definition
cholesterol in cell membrane
Term
why too much cholesterol is deadly
Definition
makes blood vessels more rigid and more likely to rupture
Term
role of HDL
Definition
takes cholesterol from peripheral tissue to liver for processing
Term
role of LDL
Definition
takes cholesterol from liver to peripheral tissue
Term
testosterone can get converted to...
Definition
androsterone
Term
the thing that causes muscle development (I think androsterone) is the same thing that causes aggression
Definition
Term
functions of progesterone
Definition
-pregnancy hormone
-prevents another egg from being fertilized
Term
birth control mimics this hormone
Definition
progesterone
Term
function of cortisone
Definition
regulates water distribution in the body

example: swelling in bee sting dilutes toxin
Term
some characteristics of prostaglandins
Definition
-very reactive
-hard to study
-made when needed
-potent
Term
some functions of prostaglandins
Definition
-pain
-swelling
-regulation
Term
prostaglandin directly involved in pain sensation when you're burned
Definition
Term
some things prostaglandins regulate
Definition
-blood pressure
-width of bronchi
-width of blood vessels
-width of iris
Term
prostaglandins can also be used for contraception
Definition
Term
how aspirin relieves pain
Definition
stops one of the prostaglandins from forming
Term
terpenes aka essential oils
Definition
liquids that have a smell (essence) and aren't water-soluble
Term
all terpenes are based on...
Definition
isoprene
Term
[image]
Definition
isoprene
Term
terpenes always contain C and H, but can contain O
Definition
Term
terpenes don't always have rings
Definition
Term
thy is this not a terpene?
[image]
Definition
because it has 5 C atoms in a straight chain; doesn't resemble isoprene
Term
β-kerotene is metabolized into retinol, which is directly related to vision
Definition
Term
excess water-soluble vitamins can be urinated out, but fat-soluble vitamins are more dangerous in excess
Definition
Term
alkaloid
Definition
secondary natural product that contains N
Term
some characteristics of alkaloids
Definition
-predominantly plant materials
-generally have bitter taste (possibly defense mechanism)
-basic due to N
-seem to be dead end in metabolism
-have stark responses in humans
Term
some examples of alkaloids
Definition
[image]
[image]
Term
[image]
Definition
glucose
Term
[image]
Definition
fructose
Term
[image]
Definition
glucose (cyclic)
Term
[image]
Definition
fructose (cyclic)
Term
[image]
Definition
Methyl α-D-glucopyranoside
Term
[image]
Definition
ethyl α-D-fructofuranoside
Term
[image]
Definition
β-D-Glucopyranose
Term
[image]
Definition
D-fructofuranose
Term
[image]
Definition
D-ribose
Term
[image]
Definition
β-D-ribofuranose
Term
[image]
Definition
ribonucleoside
Term
[image]
Definition
saponification
Term
[image]
Definition
an α-amino acid
Term
[image]
Definition
basic structure of a steroid
Term
[image]
Definition
basic structure of a prostaglandin
Term
[image]
Definition
structure of detergents
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