The chemistry of the compounds of Carbon, as well as Hydrogen, Oxygen, Nitrogen, Sulfur, Phosphorus, and a Halogen (fluorine, chlorine, bromine, iodine)
Organic Properties
Bonding is almost entirely covalent
Many are gases, liquids, or solids w/ low melting points
Most are insoluable in water
Most are soluable in organic solvents
Almost all burn and decompose
Reactions are usually slow
Bond angles and Geometries
Tetrahedral: 109.5 degrees - Single bond
Trigonal Planar: 120 degrees - Double bond
Linear Molecule: 180 degrees - Triple Bond
Functional Group
An atom or group of atoms within a molecule that show a characteristic set of predictable physical and chemical behaviors.
Define Hydrocarbon (saturated and unsaturated)
Hydrocarbon: A compound that contains only carbon and hydrogen atoms.
Saturated: Only Carbon-Carbon single bonds (alkanes)
Unsaturated: A hydrocarbon that contains one or more carbon-carbon double bonds (alkenes), triple bonds (alkynes), or benzene rings (arenes).
Constitutional Isomers
Compounds that have the same molecular formula but different structural formulas.
Iso-
Iso- indicates that one end of an otherwise unbranched chain terminates in a (CH3)2CH- group
Example: Isopropanol
Prefixes: Counting Carbons to 20
1. Meth-
2. Eth-
3. Prop-
4. But-
5. Pent-
6. Hex-
7. Hept-
8. Oct-
9. Non-
10. Dec-
11. Undec-
12. Dodec-
13. Tridec-
14. Tetradec-
15. Pentadec-
16. Hexadec-
17. Heptadec-
18. Octadec-
19. Nonadec-
20. Eicos-
Stereoisomers
Isomers that have the same connectivity of their atoms but a different orientation of their atoms in space
For any group of alkane constitutional isomers, the least branched isomer generally has the ____ boiling point and the most branched isomer generally has the ___ boiling point.
For any group of alkane constitutional isomers, the least branched isomer generally has the highest boiling point and the most branched isomer generally has the lowest boiling point.
Combustion
Alkane + O2 ---> CO2 + H2O + Heat
Markovnikov's Rule
"The Rich Get Richer" meaning hydrogen bonds to the doubly bonded carbon that has the greater number of hydrogens bonded to it; the halogen or oxygen bonds to the other carbon.
Regioselective Reaction
A reaction in which one direction of bond forming or bond breaking occurs in preference to all other directions.
Reaction Mechanism
A step-by-step description of how a chemical reaction occurs.
Arene
Term used to describe aromatic hydrocarbons (a compound containing one or more benzene-like rings)
An aldehyde can be oxidized to
An aldehyde can be oxidized to a carboxylic acid
A ketone can be reduced to
A ketone can be reduced to a secondary alcohol.
An aldehyde can be reduced to
An aldehyde can be reduced to a primary alcohol.
A primary alcohol can be oxidized to
A primary alcohol can be oxidized to an aldehyde then a carboxylic acid
Addition of an alcohol to an aldehyde produces
Addition of an alcohol to an aldehyde produces a hemiacetal
An ester is formed by the reaction between a carboxylic acid and
An ester is formed by the reaction between a carboxylic acid and alcohol
What molecules are involved in chemical communications?
Cell-to-cell communications are carried out by three kinds of molecules
1. Receptors: protein molecules embedded in the membranes of cells
2. Chemical messengers, or ligands: interact with receptors
3. Secondary messengers: carry and amplify the signals from the receptor to inside the cell
An aldehyde can be oxidized to a(an)
C. carboxylic acid
A ketone can be reduced to a(an)
B. A secondary alcohol
A primary alcohol can be oxidized to a(an)
D. Aldehyde and then a carboxylic acid
A secondary alcohol can be oxidized to a(an)
D. ketone
A primary alcohol can be oxidized to a(an)
B. aldehyde and then a carboxylic acid
An aldehyde can be reduced to a(an)
A. alcohol
Aldehydes are reduced to primary alcohols
Which reaction involves cleavage of a carbon-carbon bond?
B. reduction
Which of the following is a primary alcohol?
A. 1-hexanol
Which of the following is a secondary alcohol?
C. 2-heptanol
Which of the following is an ester?
B. ethyl acetate
Which term best describes the relationship between D-fructose and L-fructose?
D. enantiomers
To say that D- and L- are enantiomers means that they are nonsuperposable mirror images.
Which of the following has the highest boiling point?
D. butanoic acid
Carboxylic acids have high boiling points
Which compound does not exhibit hydrogen bonding?
D. CH3COCH2CH3
Only very weak dipole-dipole interactions
Which substance has an ester functional group?
D. shortening
There are ester bonds in fatty acids. Vinegar has carboxylic acid, sugar and honey have ether bonds
Which substance is chiral?
B. 2-pentanol
Of those given, which substance is most water soluble?
C. alcohol
Addition of an alcohol to an aldehyde produces a(an)
D. hemiacetal
Hemiacetals react further w/ alcohols to form acetals plus water.
Which class of products is characterized by four fused rings?
D. steroids
Purifying a liquid through vaporization followed by condensation is known as
A. distillation
Which base is found in RNA but not DNA
C. uracil
Which one of the following is not a component of nucleotides?
A. lipid
A nucleotide = Base + sugar + phosphate
An ester is formed by the reaction between a carboxylic acid and
A. alcohol
Fischer esterification: -OH from the acid and -H from the alcohol to remove the H2O and "squish together" the remaining ester.
The substances in the duodenum that emulsify fat globules into tiny droplets are
D. bile salts
Because they are eliminated in the feces, bile salts remove excess cholesterol in two ways 1) they are themselves breakdown products of cholesterol and 2) they solubilize deposited cholesterol in the form of bile salt-cholesterol particles -- micelles
Energy gained in the oxidation of food is stored in the form of
B. ATP
The removal of excess blood glucose is facilitated by this hormone through enhancing cellular uptake and inducing storage pathways.
D. insulin
What type of bonds hold together the two strands of DNA?
D. hydrogen
The arrangement of the two DNA strands in relation to each other is
D. anti-parallel
The backbone of DNA consists of _____.
Adenine, thymine, guanine, and cytosine
A-T and G-C
What is the primary function of mRNA?
F. Directs amino acid sequence of proteins
Messenger RNA
What is the primary function of tRNA?
E. Transports amino acids to site of protein synthesis
Transfer RNA
What is the primary function of rRNA?
E. Combines with proteins to form ribosomes, the site of protein synthesis
Ribosomal RNA
Which is a stronger base?
An aliphatic amine or an aromatic amine?
Aliphatic amines are a stronger base than aromatic amines.
Aromatic amines are weaker bases than aliphatic.
ethane + O2 -yields-> _____ + _____
2CH3-CH3 + 7O2 --yields--> 4CO2 + 6H2O + Heat
An alkane plus oxidation is combustion and it results in Carbondioxide plus water plus heat.
The following compounds have comparable molecular weights. Which one has the highest boiling point?
A. 2-propanol
Which statement about amines is incorrect?
B. Aliphatic amines are stronger bases than inorganic bases such as NaOH and KOH
Aromatic amines are weaker bases than aliphatic
Place the following in order of lowest to highest boiling point. Propanoic acid, 2-butanone, diethyl ether, butanal, 1-butanal, pentane
BP (C) - Name
34 - diethyl ether
36 - pentane
76 - butanal
80 - 2-butanone
117 - 1-butanol
141 - propanoic acid
All of the above compounds have comparable molecular weights... the key is in their polarity. The more polar, the stronger the hydrogen bonds, the higher the boiling points.
Hemiacetal
A molecule containing a carbon bonded to one -OH group and one -OR group; the product of adding one molecule of alcohol to the carbonyl group of an aldehyde or ketone.
The product of adding one molecule of alcohol to the carbonyl group of an aldehyde or ketone.
Hemiacetal
Acetal
A molecule containing two -OR groups bonded to the same carbon
Unbranched carboxylic acids having between 12 and 20 carbon atoms are known as ______.
Fatty acids
Cyclic esters are called ____.
Lactones
Cyclic amides are called _____.
lactams
Step-growth polymers
Step-growth polymers form from the reaction of molecules containing two functional groups, with each new bond being created in a separate step.
How do we prepare esters?
The most common laboratory method for the preparation of esters is Fischer esterification
How do we prepare amides?
Amides can be prepared by the reaction of an amine with a carboxylic anhydride.
Hydrolysis
Hydrolysis is a chemical process in which a bond is split and the elements of H2O are added.
Anomers
Monosaccharides that differ in configuration only at their anomeric carbons.
Solid animal fats contain mainly ____ fatty acids, whereas vegetable oils contain high amounts of _____ fatty acids.
Solid animal fats contain mainly saturated fatty acids, whereas vegetable oils contain high amounts of unsaturated fatty acids.
Plants use the carbohydrate _____ for energy storage, and animals use the carbohydrate _____ for storing energy.
Plants use the carbohydrate cellulose for energy storage, and animals use the carbohydrate glycogen for storing energy.
What are the major roles of lipids?
Storage: Energy stored in the form of fats.
Membrane Components: The nonpolar portion of lipids provide the water-repellent, or hydrophobic property
Messengers: Chemical messagers
Primary messengers - deliver signals from one part of the body to another
Secondary messengers - Mediate the hormonal response
Starch is composed of _____ and _____
25% Amylose and 75% Amylopectin
Amylose contains continuous ____ chains of D-Glucose.
Amylopectin contains continuous _____ chanins of D-Glucose.
Amylose contains continuous unbranched chains of D-Glucose.
Amylopectin contains continuous branched chanins of D-Glucose.
Sucrose is composed of _____ and _____
Glucose and Fructose
Maltose is composed of _____ and _____
D-glucose and D-glucose
Starch is hydrolyzed to _____
Glucose
Of the following compounds of similar molecular weight, which is the most soluble in water?
C. butanoic acid
Which is the strongest organic acid of those with the pKa given below?
C. 0.75
Which organic compound is the strongest acid of those given below?
C. Trichloroacetic acid
A compound containing two -OH groups is a _____.
A compound with hydroxyl groups on adjacent carbons is a _____.
A compound containing two -OH groups is a diol
A compound with hydroxyl groups on adjacent carbons is a glycol
Ethers react rapidly with which of the following?
A. almost nothing they make excellent solvents.
Thiols are most closely related to which of the following classes of compounds?
B. alcohols
The functional group of a thiol is an -SH (sulfhydryl) group
Pencillin contains a cyclic amide; which of the following is the name for a cyclic amide?
B. lactam
What type of alcohol is formed by the hydration of 1-butene?
C. secondary
Remember, "The rich get richer" one -H goes to the carbon with two Hs and the -OH goes to the carbon with only one H currently.
In organic compounds, which of the following elements normally forms two covalent bonds?
D. oxygen
Carbon forms four, hydrogen one, and nitrogen three.
Which of the following functional groups does not contain a carbonyl group?
D. alcohol
Carbonyl group is a C double bonded to an O (C=O)
Dodecane is a 12-carbon alkane. How many hydrogen atoms are there in dodecane?
D. 26
How many moles of molecular oxygen are consumed by the complete combustion of one mole of propane?
D. 5
Combustion equation
C3H8 + 5 O2 --yields--> 3 CO2 + 4 H2O + heat
In a phenol, which group is the substituent on the benzene ring?
D. hydroxyl
Generally, alkanes are _____ dense and _____ in water.
