CHEM 1204 Exam 2 Practice Problems ANSWER KEY
Previously learned ochem
List the functional groups
Alkene, alkyne, aldehyde, carboxylic acid, ketone, ester, ether, amine, amide
What are chiral atoms?
A carbon atom that is attached to four different groups or atoms
Which of the following molecules has a chiral center?
CH3-CH2-CH3
CH3-CH(Br)-CH2-CH3
CH3-CH2-CH2-CH2OH
CH3-CH2-COOH
What is the electron & molecular geometry of methane?
Electron: tetrahedral
Molecular: tetrahedral
What is the electron & molecular geometry of carbon dioxide?
Electron: linear
Molecular: linear
What is the electron & molecular geometry of water?
Electron: tetrahedral
Molecular: bent
What would the bond angle be in a trigonal planar molecule?
120
What would the bond angle be in a tetrahedral molecule?
109.5
Lipids
What are the general functions of lipids? (list as many as you can)
Energy storage, membrane structure, signaling
What functional groups are found in lipids
Carboxyl, ester
What organic chem reactions can be done to these functional groups?
Esterification, hydrolysis, and hydrogenation
Which of the following would lipids be soluble in?
Water
Ethanol
Hexane
Acetic acid
Explain the polarity and molecular interactions involved in the question above
Hexane is a nonpolar molecule, because it consists of only carbons and hydrogens.
Since it lacks a F, O, N atom(s) and strongly electronegative molecules, it can’t have hydrogen bonding or dipole-dipole interactions.
Identify the different classes of lipids
Fatty acids, triacylglycerides, phospholipids, steroids, waxes, eicosanoids, glycolipids, lipoproteins
Which isomer is naturally occurring?
cis
How is the other isomer made if its not natural?
Made via a hydrogenation reaction. This reaction forces the natural “bent” (cis) bond to straighten out → trans
Where is vitamin D synthesized and stored?
Made in the skin when exposed to sunlight (then sent to the liver to be converted into a form that the body can use).
Stored in fat tissues and liver
What factors affect melting point?
*stronger the force, higher the melting point
Ionic bonds > hydrogen bonding > dipole-dipole > london dispersion
Larger molecules have higher melting points (because of the increase in london dispersion forces)
Linear molecules have a higher melting point, because they can pack tightly
Polar molecules have higher melting points
Why do unsaturated lipids have lower melting points than saturated lipids?
Saturated fats have no double bonds; they are linear. The bends in the fatty acid chains of unsaturated lipids dont allow for close packing, and gives them a lower melting point
Steriods + others related
Draw out a steroid backbone
Bile salts are derived from which lipid molecule?
Cholesterol
What is the relationship between cholesterol and bile salts?
Bile salts are derived from cholesterol when the liver modifies its structure.
Bile salts help emulsify fat and regulate cholesterol levels
Excreting bile salts is a way that the body removes excess cholesterol
Are bile salts soluble in water?
They are both hydrophilic and hydrophobic, making them partially soluble in water.
What does cholesterol help with regarding cell membranes?
Maintains structure and function of cell
What are the functions of cholesterol?
Regulating membrane fluidity, providing structural support between the phospholipid bilayer, precursor to steroid hormones/vitamin D, needed for myelin sheath formation
Explain the storage and release of bile salts
Bile salts are made in the liver and stored/released from the gallbladder.
Roles of calcium
bone/teeth health, muscle function, nerve transmission, hormonal secretion, cellular functions
Roles of phosphorus
Energy metabolism, dna/rna synthesis, cell membrane, muscle function, bone remodeling and mineralization
Why is the liver important for the synthesis of vitamin D?
If the liver isn’t functioning properly, it would struggle to convert vitamin D into its active form, possibly leading to rickets
What is the main function of glucocorticoids?
Regulate metabolism and help body’s response to stress
What is the main function of mineral corticoids?
Ion balance, blood pressure
What is the primary glucocorticoid and what does it assist with?
Cortisol, commonly known as the “stress hormone” and helps the body respond to stress by increasing glucose levels & breakdown of fats/proteins
What is the primary mineral corticoid and what does it assist with?
Aldosterone, assists in maintaining electrolyte/fluid balance, and blood pressure
List out the biochemical influences for sex hormones (estrogen, testosterone) and vitamin D
Estrogen: regulation of menstrual cycles, reproductive tissue development, cognitive, bone, cardiovascular health
Testosterone: development of male reproductive tissues, muscle growth, fat distribution, bone health
Vitamin D: bone health, calcium & phosphate regulation, immune system activity, muscle function,
List the water soluble & in-soluble vitamins
Water soluble: Vitamin C and B
Fat soluble: Vitamin A, D, E, and K
Bonds and reactions
What does a lipid lack if it cannot be hydrolyzed?
Lack an ester, amide, or glycosidic bond
List the hydrolyzable lipids
Triglycerides, phospholipids, glycolipids, sphingolipids, waxes
List the non-hydrolyzable lipids
Sterols, fat-soluble vitamins, lipid-soluble hormones
What is the structure of sphingomyelin composed of?
Sphingosine backbone, fatty acid, phosphate group, choline (*or other group) attached to phosphate
List the hydrolyzable bond(s) on sphingomyelin
Amide, phosphodiester
Whats the relationship between ceramide and sphingolipids?
Ceramide is a building block of sphingolipids, serves as a precursor
What would the product be if you hydrated ethene?
Ethanol
What happens if you hydrogenate an unsaturated fatty acid?
You get a saturated fatty acid
Explain saponification
Chem reaction when a fat reacts with a strong base (such as NaOH), and the result is soap and glycerol
Explain what the saponification of vegetable oil would produce
Soap and glycerol
How do soap molecules emulsify oils?
Emulsify via their (both) hydrophobic and hydrophilic parts. The hydrophobic tails of soap molecules bind to oil, and the hydrophilic heads interact with water. This allowes the oil to be washed away from surfaces.
Fatty acids
Arachidonic acid is a carbon, omega- fatty acid
20, 6
What is arachidonic acid involved in?
Precursor to eicosanoids, inflammatory response
What food(s) have omega-3 fatty acids?
Fortified foods, fatty fish
Functions of omega-3 fatty acids
Reduce inflammation, improves heart health, brain function, eye health, skin
What food(s) have omega-6 fatty acids?
Vegatable oils, nuts, processed foods
Functions of omega-6 fatty acids
Inflammatory response, brain function, skin health
List the common diseases linked to omega-3 & omega-6 fatty acid imbalance
Heart disease, inflammatory conditions, mental health disorders
How are prostaglandins formed?
From arachidonic acid
List the physiologic effects of prostaglandins
Inflammation, pain sensation, fever, clotting
What do all prostaglandins have in common with their structure?
All cyclic compounds with a 5-membered ring, derived from arachidonic acid, have a hydroxyl group attached to ring structure
What determines their differences?
Functional groups, enzyme activity
Understand the Name format differences PGF2, PGE1 etc
P stands for prostaglandin
Letter refers to the specific type of prostaglandin
The number indicates the number of double bonds in the side chain
PGE indicates prostaglandins that have an alcohol group of carbon 15
PGF indicates prostaglandins that have a ketone group on carbon 9
What is the relationship between aspirin and prostaglandins?
Aspirin inhibits the enzyme that is responsible for converting arachidonic acid innto prostaglandins
What are waxes composed of? What is their structure?
Waxes are esters formed from the ration between a fatty acid and long-chain alcohol
Structure: ester bond between the carboxyl group of the fatty acid bonded to the hydroxyl group of the alcohol
Does wax have a high or low melting point? Why?
High melting point, because they have long hydrocarbon chains with intermolecular forces
Membrane components
Why are phospholipids an important characteristic of membranes?
Because they have both hydrophilic and hydrophobic regions, they are able to form a bilayer, which then allows the cell to be selective permeable
What lipid type has the largest % in a membrane?
Phospholipids
Why is cholesterol an important characteristic of membranes?
Membrane fluidity regulation, membrane integrity,
List and explain the two types of membrane proteins
Integral- embedded within bilayer
Peripheral- not embedded, rather attached to hydrophilic heads
Function of carbohydrates on membranes?
Cell recognition, protection, signal reception
What type of membrane transport do: glucose, amino acids, Na+, K+, and Ca2+ use? Why?
Glucose uses facilitated, because its too large and polar to freely diffuse, but transporters move glucose down concentration gradient
Amino acids use active transport, because they are polar molecules
Na+, K+, Ca2+ use active transport, because these are kept in an imbalance (think about how the imbalance changes via action potential), and need to be moved against their concentration gradient.
What are chylomicrons and what do they do?
Chylomicrons are large lipoproteins that are responsible for transporting lipids from the intestine to various tissues.
What differentiates VLDL, LDL, and HDL from one another, and where does each transport to/from?
VDLD- delivers triglycerides from liver to tissues
LDL- transports cholesterol from liver to tissues –often contributing to plaque formation if too much-
HDL- removes excess cholesterol from tissues and returns it to liver for disposal
Medical associations
What lipids are associated with an increased risk for cardiovascular disease?
High levels of LDL, triglycerides, low levels of HDL
What 4 other conditions are associated with these lipids?
Metabolic syndrome, type 2 diabetes, hypertension, atherosclerosis
What is atherosclerosis?
Condition where fatty deposits, cholesterol, and other substances build up on inner walls of arteries causing them to become narrower that constricts blood flow.
Explain fatty liver disease
Buildup of fat in the liver cells from an imbalance between fat intake and fat breakdown in the liver, often leading to obesity, insulin resistance, etc..
How is insulin resistance (type 2 diabetes) relayed to triglycerides and cholesterol?
Insulin resistance is when the body’s cells become less responsive to the effects of insulin → often leads to type 2 diabetes with blood glucose levels abnormally high.
Insulin resistance leads to increase in triglyceride levels (insulin helps ocntrol the breakdown of fats, but if body becomes resistant, fat metabolism is impaired).
Insulin resistance can also lead to formation of (small) LDL particles (resuling in more LDL and less HDL), which is a contributor to atherosclerosis and cardiovascular diseases.
List two neurological disorders that are related to lipids
Alzheimer’s disease- lipid metabolism (esp cholesterol) is disrupted → high cholesterol levels → lipid abnormalities that affect brain’s ability to clear amyloid plaques → alzheimers disease
Multiple sclerosis (MS)- autoimmune disease wheere immune system attacks (the lipid-rich) myelin → impairs transmission of signals along nerve fibers → causing inflammation, damage, and poor nerve function.