Organic Chemistry Flashcards
A combination of atoms that confers certain chemical and physical properties on a compound is called a ___
functional group
What does saturated hydrocarbon mean?
Maximum number of hydrogens attached to each carbon (no multiple bonds)
Isomers with same connectivity
Stereoisomers
Achiral isomers AKA Geometric/ Configurational isomers
Cis–trans isomers
Stereoisomers that cannot be interconverted without breaking a chemical bond
Cis-trans isomers
Achiral isomers AKA Asymmetric isomers
Optical isomers
A substance is optically active when ___
- It has chiral carbon
- When hit by polarized light, angle changes
Chiral isomers that are mirror images.
Enantiomers
Equimolar mixture of two enantiomers
Racemic mixture
Chiral isomers that are not mirror images.
Diastereomers
Isomers with different connectivity
Constitutional isomers
Markonikov’s Rule
- For HX, H attaches to double bonded C with more H, X (halogen) attaches to the more substituted carbon
Zaitev’s Rule
(Definition and when to apply)
“the rich getting richer, the poor getting poorer”
The carbon with the fewest hydrogens loses the hydrogen.
Formula Degree of Unsaturation
p= (2+2C+N-H-X)/2
Aliphatic came from word??
Greek: Aleiphar (meaning fat)
CnH2n+2
Alkane
AKA Apraffins
Alkane
AKA Olefins
Alkene
How to determine molecular formula (CxHy) of Aliphatic hydrocarbons?
a) for each double bond = 2 less H atoms
a) for each triple bond = 4 less H atoms
c) for each rings = 2 less H atoms (whenever ring is closed)
“Which is not a proper according to IUPAC nomenclature?”
“n-butyl”
kung alin merong “n-“
Notation on alkane containing Cl
chloro
C attached to two C
secondary
C attached to threeC
tertiary
C attached to fourC
quaternary
What iso means in nomenclature?
all carbons except one form a continuous chain
What neo means in nomenclature?
all but two carbons form a continuous chain
What sec means in nomenclature?
when the functional group is bonded to a secondary carbon.
What tert means in nomenclature?
when the functional group is bonded to a tertiary carbon.
Which of the following objects are chiral?
a. pair of scissors
b. beaker
c. paper clip
d. the swirl created in water as it drains out of a sink or bathtub
a. pair of scissors
How to differentiate alkane alkene and alkyne?
a. combustion on an empty beaker
b. nature of carbon and its branching
c. reaction with Br2
d. all of these
c. reaction with Br2
What compound is a ketone but it is not a carbohydrate but is useful commercially?
acetone
Focuses on the localization of electrons between atoms to form covalent bond
Lewis structure
Focuses on the delocalization of electrons to achieve stability
Resonance Structures
Culmination of contributions resonance structures
Resonance hybrid
Withdrawal or donation of electron through a sigma bond due to electronegativity and polarity of bonds in functional groups
Inductive Effect
Withdrawal or donation of electron through a pi bond due to overlap of a p-orbital on the substituent with a p-orbital on the aromatic ring.
Resonance Effect
Each bond in a benzene is considered
more than a single bond, but less than a double bond
Bonding between carbon atoms are ____
covalent and strong
Comparing Alkane Stability
a) Heat of combustion
b) number of C atoms
c) branching
a) number of C atoms: Less C = more stable
b) branching: more branching = more stable
c) Heat of combustion: inversely proportional
Comparing Alkene Stability
a) number of C atoms
b) substitution
c) Z/E or cis/trans
a) number of C atoms: Less C = more stable
b) substitution: more substituted = more stable
c) Z/E or cis/trans: E and trans = more stable
Comparing Melt pt, Boil pt and Density:
a)IMFA
b) substitution
c) number of C atoms
d) branching
a) IMFA: stronger = higher
also, more polar or symmetrical = higher
b) substitution: halogen substituted = higher (more IMFA)
c) number of C atoms: more = higher
d) branching: more = lower
Petroleum Products: (# of C’s and Phase)
a) Petroleum Gas
b) Gasoline
c) Kerosene
d) Fuel Oil
e) Lubricating Oil
f) Residue
a) Petroleum Gas: C1 to C4
Gas
b) Gasoline (naphtha): C5 to C12
Liquid
c) Kerosene: C12 to C16
Liquid
d) Fuel Oil: C15 to C18
Liquid
e) Lubricating Oil: C15 to C18
Liquid
f) Residue (asphalt): > C18
Solid
Each C-H bond of one carbon bisects the H-C-H angle of the other carbon
Staggered conformation
(hugis Y)
Substituents of one C atom in alkane does not align from other substituents
Staggered conformation
Each C-H bond of one carbon aligns with the C-H bond of the other carbons
Eclipsed conformation
How to avoid 1,3-diaxial repulsion?
in cyclohexanes
larger substituent must be in equatorial (horizontal) position
EPA
Eicosapentanoic acid
DHA
Docosapentanoic acid
ALA
Alpha-Linoleic acid
Comparing Melt pt, Boil pt and Density:
a) IMFA
b) number of C atoms
c) branching
a) IMFA: stronger = higher
b) number of C atoms: more = higher
c) branching: more = lower
SN1 or SN2:
attacks methyl or primary alcohol
SN2
SN1 or SN2:
attacks secondary or tertiary alcohol
SN1
SN1 or SN2:
more steric effect
SN1
SN1 or SN2:
tends to be racemic mixtures
SN1
SN1 or SN2:
tends to undergo 100% inversion (Cahn Ingold Prelog)
SN2
SN1 or SN2:
bimolecular reaction
SN2
SN1 or SN2:
Unimolecular reaction
SN1
SN1 or SN2:
faster reaction the more substituted the hydrocarbon is
SN1
SN1 or SN2:
faster reaction the lesser substituted the hydrocarbon is
SN2
SN1 or SN2:
Involves an intermediate reaction
SN1
SN1 or SN2:
Doubling the reagent does not change the reaction rate
SN1
SN1 or SN2:
Double the reagent will double the reaction rate
SN2
pull of electron density through sigma bonds caused by electronegativity
Inductive effect
Positively charged carbon draws electron from sigma bonds around it
Inductive Effect
Electron delocalization due to the orbital overlap between an alkyl group and the positively charged carbon
Hyperconjugation
How is a carbocation stabilized by the alkyl groups attached to it?
Hyperconjugation
Alkyl (CH) groups around carbocation C+ impart their electron density to it.
The more substituted a carbocation is, the more __ it is
the more stable it is
Alkene Nomenclature Priority:
Alcohol
Alkyl Halides
Double bond
- Alcohol
- Double bond
- Alkyl halides
Alkene Nomenclature:
Vinyl
Allyl
Vinyl C=C–
Allyl C=C-C–
Z
Zusammen
Cis = “magkaZama”
High atomic number atoms on same side
E
Entgegen
Trans = “magka-Eba”
High atomic number atoms on opposite side
Alkene Nomenclature:
Cahn Ingold Prelog Rules
1. Multipliers
2. MW
3. Next carbon
AKA E/Z Rules
1. Highest atomic number atom
2. Proceed to next bonds if 1 fails
3. Multiple bonds and branching serve as multipliers
Define Sigmatropic Rearrangements
reactions where sigma bonded substituent atom or group migrates across a pi electron system
(See QRC Notes)
Organic Chemistry Rules:
Markovnikov
*When there is no peroxides
* X substituted into carbon with lesser H
Organic Chemistry Rules:
Anti - Markovnikov
*When there is peroxides
* X substituted into carbon with more H
KEYWORD:
Hydrohalogenation with Peroxide Reagent
anti Markovnikov
Organic Chemistry Rules:
Zaitsev’s Rule
*for Hydrohalogenation (HX)
*in presence of weak-bulky and strong non-bulky bases:
lithium di-isopropyl amide (LDA)
NaOH
KOH
* Major product is alkene with most substituted double bond
Organic Chemistry Rules:
Hofmann’s Rule
- in presence of strong bulky base:
Potassium tert-butoxide (KOt-Bu)
DBN, DBU - Major product is alkene with least substituted double bond
A mass spectrum technique and is obtained by grinding up a solid which is mixed with mineral oil to from a suspension for IR spectroscopy.
Nujol Mull
LOOKSFAM :)
Glucose and fructose are examples of
A. double sugars
B. disaccharides
C. single sugars
D. polysaccharides
C. single sugars
Which of the following is NOT a polysaccharide?
A. Glycogen
B. Starch
C. Sucrose
D. Cellulose
C. Sucrose
What are used in animals as a source of quick energy that can be stored in the liver and muscles ？
A. Proteins
B. Nucleic acids
C. Carbohydrates
D. Lipids
C. Carbohydrates
Sugars, starches, and cellulose belong to which major class of biological molecules?
A. Nucleic acids
B. carbohydrates
C. lipids
D. polypeptides
B. carbohydrates
Plants like sugar cane and sugar beets store the energy as simple sugars. Other plants, like corn and potatoes, store the energy as more complex sugars called?
A. carbohydrates
B. calories
C. starches
D. cellulose
C. starches
What are the monomers of lipids?
A. Amino acids
B. Simple sugars
C. Fatty acids and glycerol
D. Nucleic acids
C. Fatty acids and glycerol
Lipids are used by the body to perform all of the following functions EXCEPT:
A. membrane structural material.
B. enzyme action.
C. insulation.
D. a rich energy source.
B. enzyme action.
What type of organic substances are fats?
A. nucleic acid
B. carbohydrate
C. protein
D. lipids
D. lipids
Fats that have fatty acids with only single covalent bonds in their carbon skeletons are
A. saturated
B. unsaturated
C. found in plants instead of animals
D. liquid at room temperature
A. saturated
Which of the following is a polymer?
A. nucleic acid
B. fatty acid
C. Amino acid
D. Glycerol
A. nucleic acid
Proteins are ____ made of amino acid ____.
polymers; monomers
In this type of structure, most of carbonyl groups of peptide bonds forms a hydrogen bond with the amide nitrogen of another peptide bond four amino acids further down the polypeptide chain:
A. Alpha-helix
B. Beta-sheet
C. Beta-turn
D. Quaternary
A. Alpha-helix
The isoelectric point of an amino acid is defined as the pH
A. where the molecule carries no electric charge
B. where the carboxyl group is uncharged
C. where the amino group is uncharged
D. of maximum electrolytic mobility
A. where the molecule carries no electric charge
The local spatial arrangement of a polypeptide’s backbone atoms without regard to the conformation of its side chains can be called as
A. Primary structure
B. Secondary structure
C. Tertiary structure
D. Quaternary structure
B. Secondary structure
Which of the following amino acids are
more likely to be found in a protein’s
interior away from aqueous solvent
molecules?
A. Val, Leu, Ile, Met, and Phe
B. Ser, Thr, Asn, Gln, and Tyr
C. Arg, His, Lys, Asp, and Glu
D. All of the above.
A. Val, Leu, Ile, Met, and Phe
Which of the following is not a characteristic
of a globular protein?
* A Polypeptide chain in extended, long sheets
* B Polypeptide chains are folded in a
spherical shape.
* C Contains several types of secondary
structure
* D Typical for regulatory proteins.
A Polypeptide chain in extended, long sheets
The alpha helix found in myoglobin can best be described as
A. Primary structure
B. Secondary structure
C. Tertiary structure
D. Motif structure
B. Secondary structure
Some parts of a protein that have a specific chemical structure and function are called protein
A. chemicals
B. domains
C. subunits
D. enzymes
B. domains
One of the following is not usually a force that helps to hold the monomer units of a quaternary protein together?
A. Peptide bonds
B. Disulfide bonds
C. Salt bonds
D. Hydrophobic interactions
A. Peptide bonds
If a person breathes into a paper bag, you would expect their blood CO2 to
A. decrease and their blood pH to increase
B. decrease and their blood pH to decrease
C. increase and their blood pH to increase
D. increase and their blood pH to decrease
D. increase and their blood pH to decrease
The quaternary structure of a protein is
A. the sequence of amino acids in the polypeptide
B. the coiling or folding of the polypeptide
C. the intertwining of two or more polypeptides
D. the 3-dimensional appearance of the polypeptide
C. the intertwining of two or more polypeptides
The action of disrupting the three-dimensional shape of a protein is termed
A. dehydration
B. denaturation
C. deamination
D. hydrolysis
B. denaturation
The bonds in protein structure that are not broken on denaturation.
* (a) Hydrogen bonds
* (b) Peptide bonds
* (c) lonic bond
* (d) Disulfide bonds
- (b) Peptide bonds
The protein portion of a conjugated enzyme is called a(n)
A) apoenzyme.
B) coenzyme.
C) holoenzyme.
D) cofactor.
A) apoenzyme.
Enzyme cofactors that bind covalently at the active site of an enzyme are referred to as .
(a) cosubstrates.
(b) prosthetic groups.
(c) apoenzymes.
(d) vitamins
(b) prosthetic groups.
AKA Coenzyme
An enzyme active site is the location in the enzyme where
* A) protein side groups are brought together by bending and folding to form a site for interactions with substrates
* B) the catalyst interactions with the enzyme
* C) catalyst molecules are generated
* D) the substrate creates the catalyst molecules
- A) protein side groups are brought together by bending and folding to form a site for interactions with substrates
What is the optimal temperature range for the majority of enzymes?
A. 40-55 ℃
B. 35-40 ℃
C. 25-30 ℃
D. 15-20 ℃
B. 35-40 ℃
An allosteric activator
A. increases the binding affinity
B. decreases the binding affinity
C. stabilizes the R state of the protein
D. both (a) and (c)
D. both (a) and (c)
Reactants of an enzyme-catalyzed reaction are known as
A. products
B. substrates
C. proteins
D. complex
B. substrates
The location on an enzyme where binding occurs is known as the
A. action point
B. enzyme
C. binding location
D. active site
D. active site
An apoenzyme
A. Includes non-protein compounds such as metal ions
B. Consists of complex organic structures which may be classified as activation-transfer coenzymes or oxidation-reduction coenzymes
C. Is the protein portion of the enzyme without the cofactors
D. None of the above
C. Is the protein portion of the enzyme without the cofactors
A competitive inhibitor of an enzyme works by
A. fitting into the enzyme’s active site
B. fitting into the allosteric site of the enzyme
C. attaching itself to the substrate, thereby preventing
the enzyme from making contact with substrate
D. increasing the activation energy of the enzyme catalyzed reaction
A. fitting into the enzyme’s active site
Where does glycolysis occur?
cytoplasm
Sports physiologists wanted to monitor athletes to determine at what point their muscles were functioning anaerobically. They could do this by checking for a buildup of which of the following compounds?
lactate
In the liver, glucagon will activate
A. Glycolysis and glycogen synthesis
B. Gluconeogenesis and glycogenolysis
C. Gluconeogenesis and glycogen synthase
D. Gluconeogenesis and glycogen synthesis
B. Gluconeogenesis and glycogenolysis
Cellular respiration takes place mostly in:
mitochondria
Enumerate Metabolic Processes in correct order
- glycolysis,
- pyruvate oxidation,
- citric acid cycle
- oxidative phosphorylation
What are the products of the citric acid cycle?
NADH, ATP, FADH2, and CO2
The TCA cycle:
A. Is found in the cytosol
B. Is controlled by the ADP/ATP ratio and the NADH concentration
C. Is also called the Cori cycle
D. Produces most of the water made in humans
B. Is controlled by the ADP/ATP ratio and the NADH concentration
The main purpose of the electron transport chain is to:
A. Use high energy electrons from other cycles to convert ADP into ATP
B. Maintain a stable balance of high energy electrons
C. Constantly distribute electrons throughout
the cell
D. Tell the cell when glycolysis should stop or start
A. Use high energy electrons from other cycles to convert ADP into ATP
