Chemistry 114 Review Questions

Chapter 12

Be able to define: alkane, R-group, isomer, combustion, functional group, empirical formula, molecular formula, structural formula, condensed formula, line formula, hydrocarbon, alkane, alkene, alkyne, alkyl halide, cycloalkane, IUPAC, primary carbon, secondary carbon, tertiary, quaternary carbon
Be able to diagram and describe an atom of carbon
Be able to list properties of C, H, O, N: how many bonds do they form, which form tetrahedral, bent, pyramidal, oxidation state commonly developed, etc.
Know which commonly encountered bonds are polar (C-O, O-H, N-H, C-Cl, C-N) and which are nonpolar (C-C, C-H)
Be able to list several properties of covalent molecules (polarity, density, solubility, etc.).
Be able to explain the properties of organic molecules, e.g., nonpolarity.
Given a molecule, be able to describe its geometry (what are the bond angles) and bonding (sp³, sp² or sp hybridized).
Be able to convert between molecular formula, structural formula, condensed formula, and line formula.
Be able to complete a table of organic functional groups. In other words, be able to indicate that an alcohol is R-OH, e.g.)
Be able to give a definition of hydrocarbon and list several examples of classes of hydrocarbons.
Be able to draw the structure of a molecule, given its IUPAC name, and vice versa.
Be able to name molecules up to 10 carbons in length (main chain). Know as R groups methyl ethyl, propyl, isopropyl, butyl, and t-butyl.
Be able to name alkyl halides (up to 10 total carbons) and compare/contrast them to the alkanes.
Be able to list and explain properties and reactions of alkanes.

Chapter 13

Be able to define: cis-trans isomer, sp hybridization, sp² hybridization, sp³ hybridization, aromatic, toluene, phenol, aniline, benzene, ortho, meta, para, sigma () bond, pi () bond
Given a IUPAC name for an alkene (molecules of the range of sizes we have been working with), be able to draw the structure, and vice versa.
Be able to predict the product of a reaction, given the reactant and reaction conditions.
Be able to tell whether an alkene is a cis or trans isomer, or neither.
Be able to name aromatic molecules that are derivatives of benzene.
Be able to compare properties of alkenes and aromatic compounds to alkanes.

Chapter 14

Be able to define: diol, primary alcohol, secondary alcohol, tertiarty alcohol, phenol, Lucas test, thiol and disulfide.
Given a IUPAC name for an alcohol or phenol, be able to draw the structure, and vice versa.
Be able to list the thiol functional group and remember for biochemistry that disulfide bonds can and do form.
Be able to name simple ethers.
Be able to predict the product of a dehydration reaction on an alcohol.
Know that alcohols can be oxidized to aldehydes and ultimately to carboxylic acids by the oxidizing agent KMnO₄.
Be able to compare the physical properties of alcohols and ethers to alkanes.
Be able to predict the product of the Lucas test on alcohols, as well as how fast the reaction occurs.

Chapter 15

Be able to define: oxidation, reduction, aldehyde, ketone, carbonyl, heteroatom, hemiacetal and acetal.
Given a IUPAC name for an aldehyde or ketone, be able to draw the structure, and vice versa.
Be able to list the "active ingredient" used in detecting aldehydes and remember the product formed which gives it the characteristic color (Tollen's test uses Ag⁺ and results in a silver mirror; and Fehling's test uses Cu⁺ and results in a brick red color).
Be able to recognize a hemiacetal () or hemiketal ().
Be able to predict the product of an aldehyde or ketone being reduced with NaBH₄ (a primary alcohol or a secondary alcohol, respectively).
Know that the physical properties of aldehydes and ketones are similar and be able to compare and contrast them to the other functional groups we have learned.

Chapter 16

Be able to define: carboxylate ion, carboxylic acid, esterification, saponification, amide, ester, phosphate ester and thioester.
Given a IUPAC name for a carboxylic acid, be able to draw the structure, and vice versa.
Remember that the H of the carboxylic acid group is ionizable, and that the protonated form is less soluble in water.
Predict the products of an acid-base reaction involving a carboxylic acid.
Know that the product of NaBH₄ reduction of a carboxylic acid is a primary alcohol.
Given an acid and an alcohol, predict the ester which will be formed.
Be able to give the IUPAC name for an ester, or draw the ester given its IUPAC name.
Be able to give the products of the hydrolysis of an ester, given acidic (hydrolyis) or basic (saponification) conditions.

Chapter 17

Be able to define: amine, amide, amine salt and ammonium salt
Given a IUPAC name for a primary or secondary amine or amide, be able to draw the structure and vice versa.
Remember that the partial double bond character in the amide causes the molecule to be more stable than esters and makes that portion of the molecule rigid.
Given an acid (carboxylic acid) and an amine, predict the amide which will be formed
Be able to predict how an amine will act in an acid-base reaction.
Be able to give the products of the hydrolysis of an amide, given acidic or basic conditions.

Cumulative Reactions to know

Alkanes, alkenes and aromatics
Oxygen-containing functional groups
Nitrogen-containing functional groups

Chapter 18

Be able to define: carbohydrate, chiral carbon, stereoisomer, epimer; ketose, tetrose, etc.; glycosidic linkage, reducing sugar, monsaccharide, disaccharide, oligosaccharide, polysaccharide, anomer
Be able to identify chiral carbons in a molecule
Be able to identify a sugar as D- or L-
Be able to describe a sugar as aldose vs. ketose, triose vs. tetrose, etc.
Remember that most naturally occuring sugars are D-sugars
Given a Fischer projection, be able to convert it to a Haworth projection, and vice versa
Remember the structure (Haworth projection only) of ribose, glucose, galactose, mannose and fructose
Understand that sugars do not exist either in ring form or open chain form, but rather that these forms are freely interchangable.
Know that one form of a sugar predominates (e.g. glucose is ~2/3 ß form) but _do_not_ memorize the percentage of sugar in any form
Know that sugars can be reduced to polyols and be able to draw the polyol resulting if you are given a sugar structure
Know that if a sugar exists as a hemiacetal, that the sugar will be a reducing sugar. Be able to apply this knowledge by looking at a structure and indicating whether it is reducing.
Be able to draw a structure if given a chemical description. For example galactose linked ß1,4 to glucose is:
Be able to identify a sugar as alpha or beta
Understand that glucose ß1,4 glucose (cellulose) is not digestible whereas glucose1,4glucose (glycogen/starch) is diestible.
Be able to explain how carbohydrates function in recognition.

Chapter 19

Be able to define: lipid, triacylglycerol, phospholipid, essential fatty acid, saturated fatty acid, unsaturated fatty acid, plasma membrane, integral protein, peripheral protein, sphingolipid.
Be able to calculate Cal (kcal) in a diet, given percent carbohydrate, lipid and fat
Be able to explain the difference between fat- and water-soluble vitamins and be able to list the members of each class
Be able to draw the structure of palmitic, stearic, palmitoleic and oleic acids
Know that naturally occuring fatty acids are cis and there are health questions surrounding the use of partially hydrogenated fats
Be able to list linoleic, linolenic and arachidonic acid as essential fatty acids
Be able to describe the difference between fats and oils
Be able to draw a triacylglycerol (TAG) if given fatty acids to use
Be able to give the products of TAG saponification or bromine treatment
Be able to describe fatty acids by theor schemes
Be able to describe fatty acids: cis, unbranched, even number carbons, etc.
Be able to draw the structure of TAG, phosphatidylethanolamine (PE), ceramide, and cholesterol
Be able to recognize molecules as a prostaglandin, thromboxane or leukotriene
Be able to describe the importance of cholesterol as a steroid precursor
Be able to describe a membrance in terms of the fluid mosaic model
Be able to discuss the selective permeability of membranes and discuss the types of membrane transport

Chapter 20

Be able to define: alpha helix, amino acid, beta sheet (parallel and antiparallel), conjugated protein, denature, essential amino acid, fibrous protein, globular protein, hydrogen bond, ioselectric pH (pI), peptide bond, pK, primary (1°) structure, protein, quaternary (4°) structure, renature, secondary (2°) structure, simple protein, tertiary (4°) structure, and zwitterion
Be able to draw the structure of some of the 20 standard amino acids in their physiologically relevant form
Be able to, given a structure, be able to categorize it as polar vs. nonpolar, aromatic vs. sulfur-containing, etc.
Be able to determine the pI of amino acids (you will be given a table of pKa values)
Be able to name small peptides
Be able to describe a peptide bond in terms or partial double bond character
Be able to describe proteins as fibrous vs. globular
Be able to list and explain the forces that hold a protein in its conformation
Be able to describe the alpha helix and beta sheet (e.g. where are the R groups located, where are h-bonds, etc.)
Be able to discuss denaturation (what causes it, how the common denaturing agents work, etc.)
Be able to list and explain some of the ways in which proteins are classified and give at least one example of each.
Be able to discuss as well as compare and contrast the levels of protein structure.

Chapter 21

Be able to define: activation energy, active site, allosteric, catalyst, enzyme, feedback inhibition, substrate, zymogen
Be able to discuss the lock-and-key and induced fit models of enzyme specificity.
Be able to tell the difference between a cofactor and coenzyme.
Given an enzyme-catalyzed reaction, be able to indicate the class of enzyme.
Be able to list the classes of enzyme and give a simple example of each.
Understand and be able to explain the difference in toxicity of fat- and water-soluble vitamins.
Be able to list and explain several factors that influence the rate of an enzyme reaction.
Be able to tell the difference between competitive, noncompetitive and uncompetitive inhibitors.

Chapter 22

Be able to define: anticodon, codon, DNA, gene, mutagen, nucleotide, Okazaki fragment, phosphodiester bond, replication, replication fork, RNA, semiconservative replication, ribosome, transcription, and translation.
Be able to diagram a replication fork and explain the processes of replication, transcription and translation.
Be able to explain the differences between rRNA, tRNA, and mRNA.
Be able to explain how rRNA, tRNA, and mRNA function in protein synthesis.
Be able to diagram a molecule of DNA.
Be able to explain the difference between DNA and RNA.
Understand that the sequence of nucleotides in DNA determines the amino acid sequence of proteins (the central dogma of information flow).