Organic & Inorganic Compounds: Structures & Properties

Organic Compounds

  • Carbon and hydrogen atoms

    • Also contain other nonmetals

    • O, S, N, P

  • Found in gasoline, medicines, shampoos, plastics, perfumes

  • Covalent bonds

  • Low melting and boiling points

  • Flammable & undergo combustion

  • Not soluble in water

Inorganic Compounds

  • High melting and boiling points

  • Ionic: soluble in water/ do not burn in air

Alkanes, Alkenes, and Alkynes

1:meth, 2:eth, 3:prop, 4:but, 5:pent, 6:hex, 7:hept, 8:oct, 9:non, 10:dec

  • Alkanes: single bond hydrocarbon

    • “ane” – methane

    • Saturated: maximum amount of hydrogen attached to carbon

  • Strong C-C bonds

    • React with oxygen gas to make CO2 and H2O in combustion reactions

    • Release energy when C-C bonds are broken

  • Alkenes: double bond hydrocarbon C=C

    • “ene” – ethene

    • Unsaturated: do not contain the maximum amount of hydrogen atoms

    • React with hydrogen gas

      • Increase the number of H atoms and eventually become alkanes

  • Alkynes: triple bond hydrocarbon

    • “yne” – ethyne

    • Unsaturated

– Strong C-C bonds

  • React with oxygen gas to make CO2 and H2O in combustion reactions

  • Release energy when C-C bonds are broken

H-C≡C-H ethyne

Structural Isomers

  • Same chemical formula – atoms connected differently

    • Affects 3D shape and function

Cis-Trans Isomers

  • Atoms attached to C atoms on the double bond may form two different structures

    • Connected in the same order but different configuration

Aromatic Compounds

  • Benzene

    • Ring of 6 C atoms each bonded to 1 H atom

    • Represented by a skeletal formula using a circle in the center

  • Dyes, paints, TNT

  • Aspirin, acetaminophen, ibuprofen

  1. An organic compound composed of carbon and hydrogen connected only by a single bond is an alkane.

  2. Hydrocarbons are the primary constituent of fuels.

  3. What is the name for a six-carbon continuous chain alkane? Hexane

  4. How many valence electrons does carbon have? 4

  5. True or false: an organic compound is a compound made from carbon and hydrogen atoms and may contain other nonmetals. True

  6. True or false: isomers are different chemical formulas connected the same. False

  7. When adding H2 to double bonds in vegetable oils, all the following are true except… These compounds are liquid at room temperature.

  8. The compound CH3CH2-SH is in the organic family known as thiols.

  9. An alcohol contains which of the following? Hydroxyl group (-OH)

Alcohols, Ethers, Thiols, and Phenols

  • Alcohol contains a hydroxyl group (-OH) CH3-OH

    • Flammable

    • Soluble to a point

    • Most are colorless

    • Liquid at room temperature

    • Contains a polar -OH group that forms hydrogen bonds with other alcohol molecules and with water

    • 1-3 carbons – soluble in water

      • Solubility decreases with an increasing number of carbons

  • Phenol contains a hydroxyl group (-OH) bonded to a benzene ring

    • Slightly soluble in water

    • Have -OH group – form H bonds with water

    • Can react with water to produce phenoxide ions

      • Nutmeg

      • Thyme

      • Cloves

      • Vanilla

  • Ether contains a C-O-C group

    • Contains an -O- between two C groups that are alkyls or aromatic rings

    • Bent structure

    • Anesthesia: loss of sensation/consciousness

      • Blocks signals to awareness centers

      • Muscular relaxation

      • Loss of memory, pain

  • Thiols contain an -SH group

    • Contain sulfur

    • Strong/bad odors

    • Cheese, onions, garlic, oysters

    • Detect gas leaks

Carbohydrates

  • Major source of energy from foods

    • Carbon

    • Hydrogen

    • Oxygen

  • Saccharides

  • Produced by photosynthesis

  • Synthesized from CO2, H2O, and energy from the sun

  • Oxidized in living cells to produce CO2, H2O, and energy

  • Monosaccharides: simplest

    • 3-7 C chains

      • 1 carbon in carboxyl group

    • Aldehyde group: aldose

    • Ketone group: ketose

    • Hydroxyl group on all C except the carbonyl C

    • Classified by the number of C

      • Triose-3, Tetrose-4, Pentose-5, Hexose-6

    • Aldopentose: 5 C with aldehyde group

    • Ketohexose: 6 C with ketone group

    • Glucose

      • Fruits, corn syrup, honey

      • Aldohextose

      • Dextrose and blood sugar

    • Fructose: obtained from sucrose

      • Ketohexose

    • Galactose

      • Not found in nature

      • Obtained from lactose (lactose = glucose + galactose)

    • Glucose: 70-90 mg/dL

    • Diabetes can cause hyperglycemia – glucose levels can rise to 450 mg/dL or higher

    • Hypoglycemia: blood glucose levels decrease to as low as 40 mg/dL

  • Disaccharides: 2 monosaccharides

    • 2 monosaccharides combined in a dehydration reaction

– maltose: malt sugar

– obtained from the hydrolysis of starch

– lactose

– sucrose

– cannot form an open chain

– cannot be oxidized in the human body – weight gain

Polysaccharides: Many Monosaccharides

– amylose

– 20% of starch

– amylopectin

– 80% of starch

– cellulose: major structural unit of wood

– cannot form hydrogen bonds with water

– insoluble in water

– cannot be digested by humans

Chirality

  • Same number of atoms but are arranged differently

  • Non-superimposable mirror image

  • Achiral: identical and superimposable

  • 1 or more chiral centers

  • Asymmetric carbon atom

    • C2H6O CH3-CH2-OH

  • The mirror image of a chiral compound cannot be superimposed

  • Enantiomers: stereoisomers that cannot be superimposed

Isomers: same molecular formula

Structural isomers: isomers that have different bonding sequences of atoms

Stereoisomers: isomers that differ in 3D arrangements of atoms around a central carbon

Enantiomers: stereoisomers that are non-superimposable mirror images

  1. Hypoglycemia is a condition in which the glucose level in the blood is lower than normal.

  2. Hyperglycemia is a condition in which the glucose level in the blood is higher than normal.

  3. People who have blood type AB are considered the universal recipient.

  4. People who have blood type O are considered the universal donors.

  5. Which of the following are found in vinegar? Acetic Acid

  6. Which group of carbohydrates cannot be hydrolyzed to give simpler carbohydrates? Monosaccharides

  7. Alkaloids are physiologically active compounds produced by plants that contain heterocyclic amines and can be found in a variety of medicines.

  8. Acid cycle, di- and tricarboxylic acids are oxidized and decarboxylated to produce energy for cells. False

  9. Pepsin is not a digestive enzyme to break down polysaccharides – salivary amylase, maltase, and sucrase are.

Carboxylic Acids, Amines, and Amides

  • Carboxylic acid contains a carboxyl group – a hydroxyl group attached to the carbon in a carbonyl group

    • Weak acids

    • Ionize in water to produce carboxylate ions and hydronium ions

    • Can lose a proton – 2 O atoms stabilize the negative charge

  • Metabolic processes

    • Glycolysis – a molecule of glucose is broken down into 2 molecules of pyruvate

    • Exercise – pyruvic acid is reduced to give lactic acid

Lipids

  • Biomolecules

  • Contain fatty acids/steroid molecules

  • Soluble in organic solvents – not water

  • Nonpolar

  • Carboxylic acid group – fatty acids

  • 4-ring structure in steroids

  • Functions

    • Cell membranes

    • Fat-soluble vitamins

    • Steroid molecules

  • Esters

    • Hydrolyzed to give fatty acids/molecules

      • Waxes, fats, oils

  • Steroids

    • No fatty acids

    • Cannot be hydrolyzed

    • 4 fused carbon atoms

Fatty Acids

  • Long, unbranched carbon chains

    • Carboxylic acid group on one end

  • 12-18 carbon atoms

  • Insoluble in water

  • Saturated: No double carbon bonds

    • Strong dispersion forces

    • Higher melting points

    • Solid at room temperature

    • Animal fats, coconut/palm oil

    • Harder to digest

    • Lots of cholesterol – plaques

  • Unsaturated: Double bonds

    • Bend the chain

    • Irregular shape

    • Fewer interactions

    • Random distribution

    • Lower melting points

  • Monounsaturated

    • Only 1 double bond

    • Oils – olive/peanut

  • Polyunsaturated

    • At least 2 double bonds

    • Cottonseed oil, corn oil, sunflower oil

  • Essential fatty acids from carbs or other fatty acids from the diet

  • Triglycerides

    • Fatty storage in the body

      • Esters of glycerol and fatty acids

      • Glycerol to glyceryl

      • Carbohydrates

    • Major source of energy storage

      • Hibernation

    • Hydrogenation reactions

      • Carbon-carbon double bonds in unsaturated fatty acids react with hydrogen gas to produce single carbon-carbon bonds

        • Margarine/shortening

    • Hydrolysis

      • Triglycerides split into glycerol and 3 fatty acids

      • Strong acid or enzyme (lipase) needed to digest

  • Trans Fatty Acids

    • Cis: same side of double carbon bonds

    • Trans: opposite side of double carbon bonds

    • Behave like saturated fatty acids

    • 2-4% of calories

    • Raise LDL (bad) and lower HDL (good)

      • Transport nonpolar lipids/cholesterol to cells in the liver

    • Milk, eggs, beef

    • Hydrogenation

      • Deep fried food

      • Bread, cookies

      • Chips

Phospholipids

  • Main component of the cell membrane

  • Glycerophospholipids

    • 2 fatty acids form an ester bond with the 1st and 2nd hydroxyl groups of glycerol

    • The 3rd hydroxyl group forms an ester with phosphoric acid to form another phosphoester bond with an amino alcohol

    • Polar head: ionized amino alcohol and phosphate portion

      • Strongly attracted to water

    • Nonpolar tails: only soluble in lipids

    • Most abundant lipid

    • Main structural component of cell membranes

  • Sphingomyelin

    • No glycerol – sphingosine instead

    • Forms the membranous myelin sheath that surrounds nerve cells

Steroids: Cholesterol, Bile Salts, and Hormones

  • Cholesterol

    • Most abundant steroid

    • Hydroxyl group

    • Double carbon bonds

    • Meats, milk, eggs

    • Broken down by the liver

    • Cell membranes, brain and nerve tissue, vitamins

    • Clogged arteries – atherosclerosis

  • Bile Salts: aid in protein digestion

    • Synthesized in the liver from cholesterol

    • Stored in the gallbladder

    • Polar and nonpolar regions

    • Help absorb cholesterol

    • Large amounts of cholesterol can form gallstones

  • Steroid Hormones

    • Chemical messengers

    • Produced from cholesterol

    • Male: testosterone/androsterone

    • Female: estrogen/progesterone

    • Adrenal corticosteroids

    • Anabolic steroids: not made naturally

      • Increase muscle mass

Cell Membrane

  • Diffusion: higher concentration to lower concentration

  • Facilitated transport: protein channels to increase the rate of diffusion

  • Active transport: against the concentration gradient – requires energy

  • Separates internal cellular content from the external environment

  • Lipid bilayer: 2 rows of phospholipids

  • Fluid mosaic model

    • Proteins and cholesterol are embedded in the lipid bilayer of phospholipids

    • The bilayer forms a membrane barrier with polar heads at the membrane surface and the nonpolar tails away from the water

Proteins

  • Polymers are made from 20 different amino acids

  • Characteristics vary based on the amino acid arrangement of proteins

  • Function as enzymes: regulate biological reactions

  • Peptide bond

    • Amide bond

    • -COO- group of one amino acid reacts with the

    • -NH3 group of the next amino acid

  • Peptide: the linking of two or more amino acids by peptide bonds

  • Polypeptide: a chain of 50 or more amino acids

  • Has biological activity

  • Globular proteins

    • Compact spherical shape

    • Water-soluble

    • Synthesis, transport, metabolism

  • Fibrous proteins

    • Alpha keratins – hair, nails

    • Beta keratins – feathers

  • Primary structure: the sequence of amino acids in a polypeptide chain

  • Secondary structure: local folding patterns like alpha-helix and beta-sheets

  • Tertiary structure: overall 3D shape of a single polypeptide chain

  • Quaternary structure: arrangement of multiple polypeptide subunits within a protein complex

Enzymes

  • Proteins

  • Biological catalysts

  • Active sites that bond to a substrate

  • Catalyze chemical reactions in cells

  • Catalyze a specific reaction for a specific substrate

  • Increase the rate of reactions, which requires lower energy