| 4797331247 | How does oxidation state increase? | More bonds to hetero-atoms (O, N, P) | | 0 |
| 4797331248 | How does oxidation state decrease? | More bonds to hydrogen | | 1 |
| 4797331249 | Difference between aldehydes and ketones: | Aldehydes: chain terminating
Ketones: carbonyl group in the middle of carbon chain | | 2 |
| 4797331250 | Carboxylic acids contain what two groups? | Carbonyl and hydroxyl group | | 3 |
| 4797331251 | Highest priority functional group: | Carboxylic acids | | 4 |
| 4797331252 | Structural Isomers: | Share molecular formula and weight | | 5 |
| 4797331253 | Stereoisomers: | Share molecular formula and connectivity
Differ in how they're arranged in space | | 6 |
| 4797331254 | Conformational isomers: | Differ in rotation around a single bond | | 7 |
| 4797331255 | Configurational isomers: | Interconverted by breaking bonds | | 8 |
| 4797331256 | Does a molecule want to stay in a high energy state or a low energy state? | Low | | 9 |
| 4797331257 | Three types of ring strain: | Angle strain
Torsional strain
Non-Bonded strain | | 10 |
| 4797331258 | Angle strain: | Bond angles deviate from ideal values by being stretched or compressed | | 11 |
| 4797331259 | Torsional strain results from: | Cyclic molecules assuming conformations that have eclipsed or gauche interactions | | 12 |
| 4797331260 | Non-Bonded strain results from: | Non-adjacent atoms or groups compete for the same space | | 13 |
| 4797331261 | Axial position: | H atoms sticking up or down | | 14 |
| 4797331262 | Equatorial position: | H atoms sticking out | | 15 |
| 4797331263 | Bulkiest group on a chair conformation will favor what position? | Equatorial to avoid non-bonded strain | | 16 |
| 4797331264 | Chiral molecules are characterized by: | Four different substituents | | 17 |
| 4797331265 | Principle Quantum Number (n): | Essentially a measure of size
Smaller number = closer to nucleus & lower energy | | 18 |
| 4797331266 | Azimuthal Quantum Number (l): | Subshells within an electron shell
Ranges from 0 to n-1 | | 19 |
| 4797331267 | What do the azimuthal quantum numbers 0, 1, 2, and 3 correspond to? | s, p, d, and f subshells | | 20 |
| 4797331268 | Magnetic Quantum Number (ml): | Orbitals within subshells
Ranges from -l to l | | 21 |
| 4797331269 | How many electrons are in each orbital? | 2 | | 22 |
| 4797331270 | One pi bond on top of a sigma bond = | Double bond | | 23 |
| 4797331271 | Two pi bonds and two sigma bonds = | Triple bond | | 24 |
| 4797331272 | How are hybrid orbitals formed? | By mixing different types of orbitals | | 25 |
| 4797331273 | When are resonance structures favored? (2) | 1. Lack formal charges
2. Form full octets on electronegative atoms | | 26 |
| 4797331274 | Why is a single bond stronger than a pi bond? | Because s orbitals have more overlap than p orbitals | | 27 |
| 4797331275 | When Lewis acids and bases interact they form what kind of bond? | Coordinate covalent | | 28 |
| 4797331276 | Lewis Acid is an electron ______ | Acceptor | | 29 |
| 4797331277 | Lewis Acids tend to be electrophiles/nucleophiles while Lewis Bases tend to be electrophiles/nucleophiles | Electrophiles
Nucleophiles | | 30 |
| 4797331278 | Lewis Base is an electron _______ | Donator | | 31 |
| 4797331279 | Lewis Bases often carry a ______ charge | Negative | | 32 |
| 4797331280 | Covalent bond: | Bond in which both electrons came from same atom | | 33 |
| 4797331281 | Bronsted-Lowry Acids are proton ______ | Donators | | 34 |
| 4797331282 | Bronsted-Lowry Bases are proton _______ | Acceptors | | 35 |
| 4797331283 | Why is the CN bond of an amide planar? | Partial double bond character due to resonance | | 36 |
| 4797331284 | How are peptide bonds cleaved?
How are amino acids synthesized? | Hydrolyzation reaction by strong acid or base
Condensation reaction | | 37 |
| 4797331285 | Ka: | Acid dissociation constant
Measures strength of acid in solution | | 38 |
| 4797331286 | Acids with pKa < _____ dissociate completely in solution | -2 | | 39 |
| 4797331287 | The more electronegative the atom the higher the basicity/acidity | Acidity | | 40 |
| 4797331288 | Which three functional groups can act as acids? | Carboxylic acids, alcohols, and aldehydes | | 41 |
| 4797331289 | Which two functional groups can act as bases? | Amines and amides
N can form covalent bonds by donating lone pair | | 42 |
| 4797331290 | Nucleophilicity increases with _____ | Increasing electron density (more negative charge) | | 43 |
| 4797331291 | Nucleophilicity decreases with ______ | Increasing electronegativity and with bulkier molecules | | 44 |
| 4797331292 | How do polar solvents affect nucleophilicity? | Inhibits nucleophilicity
H+ protonate nucleophile so it can't react with electrophile | | 45 |
| 4797331293 | Nucleophilicity increases _____ the periodic table in polar protic solvents | Down | | 46 |
| 4797331294 | In aprotic solvents nucleophilicity relates directly to ___ | Basicity | | 47 |
| 4797331295 | Electrophiles are generally ______ charged | Positively charged | | 48 |
| 4797331296 | What make the best leaving groups? Why? | Weak bases. They have an extra set of electrons | | 49 |
| 4797331297 | Two steps in a SN1 reaction: | 1. Formation of carbocation
2. Nucleophilic attack | | 50 |
| 4797331298 | What is the rate limiting step in an SN1 reaction? | Formation of carbocation (1st step) | | 51 |
| 4797331299 | What affects the rate of an SN1 reaction? | Concentration of substrate (1st order reaction) | | 52 |
| 4797331300 | In SN2 reactions, what affects rate of reaction? | Concentration of substrate and nucleophile | | 53 |
| 4797331301 | Which type of reaction causes the position of substituents around the carbon to be inverted? | SN2 | | 54 |
| 4797331302 | What happens in an SN2 when the nucleophile and leaving group have the same priority? | Inversion will also correspond to change in absolute configuration (R to S or S to R) | | 55 |
| 4797331303 | Why are nucleophiles and electrophiles considered kinetic properties? | Because they're involved in the rate of the reaction | | 56 |
| 4797331304 | Oxidation: (3) | 1. Loss of electrons
2. Increasing number of bonds to oxygen or atoms besides carbon and hydrogen
3. Less electronegative atom replaced by more electronegative atom | | 57 |
| 4797331305 | Reduction: (2) | 1. Gain of electrons
2. Increasing number of bonds to hydrogen | | 58 |
| 4797331306 | Oxidizing agent: | Accepts electrons from another species
Said to be reduced | | 59 |
| 4797331307 | Common oxidizing agents often contain: | Metals bonded to large number of oxygen atoms | | 60 |
| 4797331308 | Good reducing agents are ____ and have ____ and ____ | 1. Metals bound to hydride ions (H-)
2. Low electronegativity and ionization energy | | 61 |
| 4797331309 | SN1 reactions prefer _____ carbons because | Tertiary
3 > 2 > 1
The more substituted it is, the more the alkyl groups act as electron donors, stabilizing the positive charge | | 62 |
| 4797331310 | SN2 reactions prefer _____ carbons because | Primary
1 > 2 > 3
Steric hinderance is a barrier | | 63 |
| 4797331311 | What are the two reactive centers of carbonyl containing compounds? | Carbonyl Carbon
Alpha Hydrogens | | 64 |
| 4797331312 | Are hydroxyl hydrogens on phenols acidic or basic? Why? | Acidic due to resonance with phenol ring | | 65 |
| 4797331313 | Aromatic alcohols are called: | Phenols | | 66 |
| 4797331314 | Two functional groups on adjacent carbons of a phenol are called: | Ortho (o) | | 67 |
| 4797331315 | Two groups separated by a carbon on a phenol are called: | Meta (m) | | 68 |
| 4797331316 | Two groups on opposite sides of a phenol are called: | Para (p) | | 69 |
| 4797331317 | Prominent property of alcohols: | Capable of intermolecular hydrogen bonding which results in higher melting and boiling points | | 70 |
| 4797331318 | When does hydrogen bonding occur: | When H atoms are attached to highly electronegative atoms like N O or F | | 71 |
| 4797331319 | As more alkyl groups are added to non-aromatic alcohols, the compound becomes ______ acidic because _____ | Less
They donate electron density destabilizing negative charge | | 72 |
| 4797331320 | The oxidation of primary alcohols by a strong oxidizing agent will produce a ______ | Carboxylic acid | | 73 |
| 4797331321 | The oxidation of secondary alcohols by a strong oxidizing agent will produce a _____ | Ketone | | 74 |
| 4797331322 | Are hydroxyl groups of alcohols good or bad leaving groups for nucleophilic substitution reactions? | Bad | | 75 |
| 4797331323 | Two functions of mesyl and tosyl groups: | 1. Making OH better leaving groups
2. Serve as protecting groups when we don't want alcohols to react | | 76 |
| 4797331324 | Treatment of phenols with oxidizing agents produces: | Quinones | | 77 |
| 4797331325 | Two characteristics of quinones: | 1. Resonance stabilized electrophiles (accept electrons)
2. Lack classic aromatic conjugated ring structure | | 78 |
| 4797331326 | Ubiquinone: | Biologically active quinone
Can be oxidized or reduced
Acts an electron carrier for complexes I II and III of ETC (Also called coenzyme Q) | | 79 |
| 4797331327 | Is ubiquinone lipid soluble? Why or why not? | Yes, long alkyl chain allows it to be lipid soluble which allows it to act as an electron carrier within the phospholipid bilayer | | 80 |
| 4797331328 | Three other biological molecules that undergo oxidation and reduction reactions: | FADH2; NADH; NADPH | | 81 |
| 4797331329 | Do aldehydes and ketones act as nucleophiles or electrophiles? | Electrophiles | | 82 |
| 4797331330 | Is an aldehyde or ketone more reactive to nucleophiles? Why? | Aldehyde
Less steric hinderance | | 83 |
| 4797331331 | Why are alpha hydrogens of aldehydes acidic? | Because oxygen pulls electron density out of the alpha H-C bonds making them easy to de-protonate | | 84 |
| 4797331332 | When in ____ solutions alpha H easily deprotonate | Basic | | 85 |
| 4797331333 | Adding electron donating groups (ex: NH2) destabilizes the negative charge decreasing ______ | Acidity | | 86 |
| 4797331334 | Do electron withdrawing groups (like oxygen) stabilize or destabilize organic anions? | Stabilize | | 87 |
| 4797331335 | Two isomers which differ in the placement of a proton and the double bond are called: | Tautomers | | 88 |
| 4797331336 | The equilibrium between enol and keto tautomers lies far to the _____ side | Keto | | 89 |
| 4797331337 | The enol carbanion results from what? | The deprotonation of the alpha carbon by a strong base | | 90 |
| 4797331338 | Once deprotonated by a base, what happens to the enol carbanion? | It is a nucleophile that can react with electrophiles | | 91 |
| 4797331339 | Given a ketone has two different alkyl groups what two products can be formed? | A kinetically enolate and a thermodynamic enolate | | 92 |
| 4797331340 | Kinetic enolate is formed by? What results? | Less substituted alpha hydrogen removed
Double bond to the less substituted alpha carbon | | 93 |
| 4797331341 | Thermodynamic enolate is formed by? What results? | More substituted alpha hydrogen removed
Double bond is with the more substituted alpha carbon | | 94 |
| 4797331342 | Is the kinetic or thermodynamic enolate formed faster? Which is more stable? | Kinetic is formed more rapidly
Thermodynamic is more stable | | 95 |
| 4797331343 | Kinetic enolate is favored in what kind of reaction? (4) | Rapid
Irreversible
Lower temperatures
Strong sterically hindered base | | 96 |
| 4797331344 | Thermodynamic enolate is favored in what kind of reaction? (4) | Higher temp
Slow
Reversible
Weaker, small bases | | 97 |
| 4797331345 | Imine is a compound that contains what kind of bond? | CN double bond | | 98 |
| 4797331346 | In aldol condensation an aldehyde or ketone acts as an electrophile in ____ form and a nucleophile in ____ form | Keto; enol | | 99 |
| 4797331347 | Enol is composed of:
Keto is composed of: | OH and double bond
C double bond O | | 100 |
| 4797331348 | What is the end result of an aldol condensation? | Carbon carbon bond | | 101 |
| 4797331349 | Why is an enolate more nucleophilic than an enol? | Because it is negatively charged | | 102 |
| 4797331350 | With a strong base and high temperatures what happens to the product of an aldol condensation? | A dehydration occurs and a water molecule is kicked off and a double bond forms | | 103 |
| 4797331351 | What is needed to reverse an aldol condensation? | Aqueous base and heat | | 104 |
| 4797331352 | How are carboxylic acids different than aldehydes and ketones? | Additional OH permits hydrogen bonding and provides another acidic H to participate in reactions | | 105 |
| 4797331353 | What causes carboxylic acids to have such high boiling and melting points? | Mutliple hydrogen bonds | | 106 |
| 4797331354 | Why are carboxylate anions so stable? | The OH is deprotonated which means there's a delocalized negative charge | | 107 |
| 4797331355 | Lower pKa values indicate _____ acids | Strong | | 108 |
| 4797331356 | Why are dicarboxylic acids more acidic than monocarboxylic acids? | Because dicarboxylic have two oxygen atoms which are electron withdrawing | | 109 |
| 4797331357 | Once a proton is removed from a carboxylic acid, what happens to its acidity? | Immediate decrease | | 110 |
| 4797331358 | What is the effect of adding electron withdrawing substituents to carboxylic acids? | Increased ACIDITY and STABILITY | | 111 |
| 4797331359 | How can carboxylic acids be prepared? | Oxidation of aldehydes and alcohols. Oxidant is usually KMnO4 | | 112 |
| 4797331360 | What happens in a nucleophilic acyl substitution? These reactions are favored by what? | Nucleophilic molecule replaces leaving group
Favored by good leaving group | | 113 |
| 4797331361 | What makes a good leaving group? | Weak bases | | 114 |
| 4797331362 | Esters are a hybrid between what two functional groups? | Carboxylic acid and ether (ROR') | | 115 |
| 4797331363 | Esterification is what type of reaction? | Condensation
Water is a side product | | 116 |
| 4797331364 | Carboxylic acids can be reduced to primary alcohols by the use of what reagent? | Lithium aluminum (LiAlH4) | | 117 |
| 4797331365 | Saponification: | Mixing long chain carboxylic acids with lye (Na or KOH) resulting in formation of a salt (soap) | | 118 |
| 4797331366 | Product of carboxylic acid and amine: | Amide (RCONR) | | 119 |
| 4797331367 | Amides, esters, anhydrides are formed by what type of reaction? | Condensation with a carboxylic acid
Combines the two into one while losing a water molecule | | 120 |
| 4797331368 | Only _____ amines will undergo condensation reaction with carboxylic acid | Primary and secondary | | 121 |
| 4797331369 | How are esters formed? | Carboxylic acids/anhydrides and alcohols condense into esters under acidic conditions | | 122 |
| 4797331370 | When esters are formed the suffix _____ replaces -oic acid | -oate | | 123 |
| 4797331371 | Why do esters have lower boiling points than carboxylic acids? | They lack hydrogen bonding | | 124 |
| 4797331372 | What are triacylglycerols? | Esters of long-chain carboxylic acids (fatty acids) and glycerol | | 125 |
| 4797331373 | In saponification, fats are hydrolyzed under _____ conditions to produce soap. Subsequent _____ of soap regenerates fatty acids | Basic; acidification | | 126 |
| 4797331374 | Anhydrides are formed from: | Condensation of two carboxylic acids | | 127 |
| 4797331375 | Rank in order of most to least reactive?
Amides, Anhydrides, Esters | Anhydrides
Esters
Amides | | 128 |
| 4797331376 | Why are anhydrides most reactive out of the group of carboxylic acid derivatives? | Because they have resonance stabilization and three electron withdrawing O atoms
Most electrophilic | | 129 |
| 4797331377 | Why are amides the least reactive out of the group of carboxylic acid derivatives? | They contain an electron donating amino group | | 130 |
| 4797331378 | Electrons are more attracted to atoms that are more ____ | Electronegative | | 131 |
| 4797331379 | What is responsible for increased rate of hydrolysis in B-lactams? | Ring strain (eclipsing interactions) | | 132 |
| 4797331380 | Nucleophiles are electron _____ | Donating | | 133 |
| 4797331381 | What happens when anhydrides are heated? | They tend to form rings | | 134 |
| 4797331382 | The 20 naturally occurring amino acids are all ___ isomers so the Fischer projection is drawn with the amino group on the _____ and have ___ conformations | L
Left
S | | 135 |
| 4797331383 | Because amino acids are amphoteric they can act as: | Both acids and bases | | 136 |
| 4797331384 | In basic solutions, AA can be fully ____ while in acidic solutions, AA can be fully _____ | De-protonated
Protonated | | 137 |
| 4797331385 | COOH is _____ and can be ______ while
NH2 is _____ and can be ______ | Acidic; de-protonated
Basic; protonated | | 138 |
| 4797331386 | Hydrolysis of a peptide bond is catalyzed by what? | Strong acid or base | | 139 |
| 4797331387 | Phosphorous is found: | In the backbone of DNA in phosphodiester bonds linking the sugar moieties of the nucleotides | | 140 |
| 4797331388 | When a new nucleotide is joined to a growing strand of DNA by ____ it releases ____ | DNA polymerase
An ester dimer of phosphate (pyrophosphate) or PPi | | 141 |
| 4797331389 | The hydrolytic release of PPi provides energy for what? | Formation of new phosphodiester bond | | 142 |
| 4797331390 | Why is Phosphoric Acid a good buffer? | It has three hydrogens with pKa values
Can pick up/give off protons depending on pH of solution | | 143 |
| 4797331391 | AA undergo _____ to form peptide bonds. The reverse reaction is _____ of the peptide bond catalyzed by _____ | Condensation
Hydrolysis by strong acid or base | | 144 |
| 4797331392 | What does spectroscopy measure? | Energy differences by determining frequencies of electromagnetic radiation absorbed by molecules | | 145 |
| 4797331393 | Infrared Spectroscopy (IR): | Measures molecular vibrations (bond stretching, bending) by measuring absorbance
By determining what bonds exist we can infer what functional groups are present | | 146 |
| 4797331394 | IR: for absorption to be recorded, vibration must result in what? | Change in bond-dipole moment | | 147 |
| 4797331395 | OH bond peaks: | Broad around 3300 cm-1 | | 148 |
| 4797331396 | NH bond peaks | Sharp around 3300 cm-1 | | 149 |
| 4797331397 | C double bond O peaks: | Sharp around 1750 cm-1 | | 150 |
| 4797331398 | What does UV spectroscopy measure? | Extent of conjugation
More conjugation = lower energy | | 151 |
| 4797331399 | With NMR chemically equivalent protons means: | The protons have the same magnetic environment
Ex: three H on a methyl group are chemically equivalent and resonate at the same frequency because each proton sees an identical environment | | 152 |
| 4797331400 | NMR: Height of each peak is proportional to: | Number of protons it contains
Higher the peak = More protons | | 153 |
| 4797331401 | NMR: When would a proton be farther down (6-8) on the x axis? | Attached to a carbon with electronegative atoms
Atoms pull electron density away from surrounding atoms. The more density is pulled away the less it can shield itself from the applied magnet | | 154 |
| 4797331402 | NMR shifts:
Alkyl groups:
Alkenes:
Alkynes:
Aldehydes:
Aromatics:
Carboxylic Acids: | 0-3
4-6
3-4
9-10
6-9
10-12 | | 155 |
| 4797331403 | What three intermolecular forces affect solubility? | H bonding: alcohols/acids move most easily into aqueous layer
Dipole interactions: less likely to move into aqueous layer
Van der Waals: least likely to move into aqueous layer | | 156 |
| 4797331404 | What must be true about two solvents used for an extraction to work? | Must have different polarities | | 157 |
| 4797331405 | How does distillation work? | Liquid with lower boiling point vaporizes first; Temperature kept low so liquid with higher boiling point won't boil and remain liquid in the initial container | | 158 |
| 4797331406 | Why do we use vacuum distillation to distill a liquid with a BP over 150C? | The pressure is lowered decreasing the temperature that the liquid must reach in order to boil | | 159 |
| 4797331407 | Concept of chromatography: | The more similar a compound is to its surroundings the more it will stick to and move slowly | | 160 |
| 4797331408 | The eluent in TLC is usually a _____ solvent
Because of this the more non-polar the sample is the _____ it will move up the plate | Polar
Further | | 161 |
| 4797331409 | TLC Rf factor = | Distance spot moved/Distance solvent front moved | | 162 |
| 4797331410 | Ion exchange chromatography: | Beads in column coated with charged substances so they attract or bind compounds that have an opposite charge | | 163 |
| 4797331411 | Size exclusion chromatography: | Beads contain tiny pores of various size which allow small compounds to enter and slowing them down while large compounds can't fit into the pores so they will move around them and travel through the column faster | | 164 |
| 4797331412 | Affinity chromatography: | Protein of interest bound by creating column with high affinity for that protein (protein is retained in column) | | 165 |
