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49 Cards in this Set
- Front
- Back
List the six important strong acids
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HCl
HBr HI sulfuric acid nitric acid Perchloric Acid (HClO4) |
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List strong bases
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Lithium Hydroxide: LiOH
Sodium Hydroxide: NaOH Potassium Hydroxide: KOH Rubidium Hydroxide: RbOH Calcium Hydroxide: Ca(OH)2 Strontium Hydroxide: Sr(OH)2 Barium Hydroxide: Ba(OH)2 Alkoxide Ions NaH |
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Solubility Rules
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Soluble:
All salts of alkali metals All salts of ammonium All salts of Nitrate (NO3)- Cl-, Br-, I- salts are soluble, except with Hg, Ag, Pb. Sulfate salts are soluble except with Ca Sr Ba and Pb Insoluble: Metal Oxides, except alkali metals and CaO, SrO, and BaO, which forms corresponding metal hydroxides Hydroxides, except with alkali metals and Ca, Sr, Ba Carbonates, Phosphates, Sulfides, sulfites are insoluble, except alkali metals and ammonium. |
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Electronic Geometry:
Regions of electron density: 2 3 4 5 6 |
2 - linear
3 - trigonal planar 4 - tetrahedral 5 - trigonal bipyramidal 6 - octahedral |
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Reactivity of Carboxylic Acid Derivatives
From most reactive to least reactive |
1. Acyl Chloride (acid chloride)
2. Anhydride 3. Carboxylic Acid 4. Ester 5. Amide |
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1. Good leaving groups
2. Bad leaving groups |
1. Chloride anion, carboxylate anion, water(H2O+)
2. Hydroxyl group, alkoxide anion, NH2 |
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Electron Donating / Withdrawing Effects
1. Activating (Most to Least 2. Deactivating (Most to Least) |
1. oxide O-
tertiary amine secondary amine primary amine hydroxyl group ether Amide Ester alkyl group benzyl group vinyl group 2. Nitro group quaternary amine ammonium S=O=O-OH nitrile CF3 Acyl Chloride Carboxylic acid Ester Ketone Aldehyde Halogen (ortho-para directing) |
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Dehydrohalogenation
1. Type of mechanism 2. What kind of base 3 What kind of substrate 4. What happens |
1. E2
2. Strong, Bulky 3. Alkyl Halide 4. Strong bulky base is too big to be a nucleophile. So, it rips off a hydrogen. The halide drops off, and alkene is formed. This all occurs in one step. |
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Dehydration of alcohol
1. What kind of reaction 2. Substrate 3. What reaction conditions, intermediate step 4. Product |
1. E1
2. Alcohol 3. Acid, which protonates the alcohol, makes water, a good leaving group. Leaves carbocation. Rearrangement may occur. Water takes neighboring hydrogen, double bond is formed. 4. alkene. Zaitsev arrangement |
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Catalytic hydrogenation
1. substrate 2. Catalyst, type of catalyst 3. What kind of addition 3. Thermodynamics? |
addition of h2 to an alkene to form an alkane
1. alkene 2. Pd, heterogeneous 3. syn addition 4. exothermic reaction |
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Oxidation of alkenes:
Ozonolysis 1. What is the oxidizing agent 2. What does it do to an alkene |
1. Ozone, O3 (high energy)
2. Cleaves right through the double bonds, and bandages them with an O. leaves carbonyl groups. |
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Oxidation of alkenes:
Permanganate and Heat 1. What does it do to an alkene |
KMnO4 cleaves right through the double bond, and bandages with an O, leaving a carbonyl group. Additionally, it will oxidize any remaining aldehydes to carboxylic acids.
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Oxidation of alkenes:
Cold Permanganate 1. What does it do to an alkene 2. What is this called? |
Does NOT cleave right through. Adds a hydroxyl group to both double bonded carbons. Forms a glycol.
2. Hydroxylation |
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Oxidation of alkenes: Addition of Osmic tetroxide (OsO4)
1. What does it do |
Like KMnO4 in the cold, it forms a glycol.
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Electrophilic Addition to an Alkene
1. What is generally being added 2. Where does it add 3. What is this addition called |
1. HBr
2. Most substituted carbon 3. Markovnikov |
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Electrophilic addition to an alkene: Anti-markovnikov
1. What can be done to make the reaction proceed in the anti-markovnikov fashion? 2. Where does the addition of the bromine take place? 3. What is the only thing that can add to an alkene in this fashion? |
1. Carry out the reaction in the presence of peroxides, or UV light, or oxygen (anything that produces free radicals)
2. Least substituted carbon. Antimarkovnikov (free radical attaches to most substituted carbon) 3. Hydrogen Bromide |
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Oxymercuration Demurcuration
1. What kind of reaction 2. Substrate 3. Reaction conditions 4. orientation |
1. Electrophilic addition, hydroxylation
2. Alkene 3. HgOAc, NaBH4 4. Markovnikov |
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Hydration of an alkene
1. what is it 2. What are the reaction conditions 3. What kind of reaction (Markovnikov, antimarkovnikov?) 4. This reaction is the reverse of... |
1. Addition of water to an alkene to form an alcohol
2. Cold, dilute acid 3. Markovnikov addition 4. Dehydration of an alcohol |
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Hydroboration:
1. What it does 2. Reaction conditions |
1. hydrates an alkene in anti markovnikov addition
2. BH3, H2O2 |
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Halogenation of alkenes
1. Reaction conditions 2. Type of reaction 3. Orientation of reaction 4. Interesting intermediate |
1. Adding X2
2. Electrophilic additions 3. Anti addition 4. Cyclonium ion |
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Grignard Reaction
1. What does it do 2. Reaction conditions |
1. Adds an alkyl group to a ketone or aldehyde to form an alcohol
2. MrBr+ -R -R acts as a nucleophile |
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Synthesis of alkyl halides using alcohol as a reactant
1. What do you add? What does that do? 2. end product |
1. HCl or other strong acid to protonate hydroxyl group to make it a good leaving group.
2. alkyl halide. |
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Tautomerization
1. What is the functional group(s) in question 2. Describe how they are acidic 3. How to form enol |
1. Aldehydes and ketones
2. alpha hydrogen can be donated. Conjugate base is stabilized by partial positive charge of carbonyl carbon 3. Alpha hydrogen jumps to carbonyl oxygen, which takes up two electrons from carbonyl double bond. Electons that originally held the hydrogen form the enol double bond. |
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Nucleophilic addition of alcohol to an aldehyde or ketone
1. What is the nucleophile? 2. What are reaction conditions for first alcohol addition? 3. What is the product? 4. What are the reaction conditions for the second addition of alcohol? 5. What is the product? 6. Cool thing about this reaction? |
1. Alcohol. One of the lone pairs of electrons on the oxygen attacks the carbonyl carbon. The H drops off and protonates the carbonyl oxygen.
2. Acidic or Basic 3. Alcohol and OR group (hemiacetal or hemiketal) 4. Acidic (must be acidic so hydroxyl group can be protonated and fall off) 5. Carbon with two OR groups(acetal or ketal) 6. It can be reversed just by adding acid, and you get aldehyde or ketone back. Used as a blocking agent, when you want to reduce other groups, like esters, but not aldehydes and ketones. 2. |
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What happens when you mix water with aldehydes and ketones?
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establish equilibrium with geminal diol.
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Aldol condensation
1. What category of reaction? 2. What are the reactants? 3. What is the nucleophile? 4. What is the electrophile? |
1. Nucleophilic addition
2. An aldehyde or ketone reacting with itself, or another aldehyde or ketone 3. A negatively charged alpha carbon after it has released its alpha hydrogen. 4. The carbonyl carbon of the other aldehyde/ketone |
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Decarboxylation:
1. Removal of a... |
Carboxylate group
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Fisher esterification
1. What are the reactants 2. What are the reaction conditions 3. What happens 4. Which oxygen is obtained in the product 5. What is the product |
1. Carboxylic acid and alcohol
2. Acidic 3. Acid protonates the hydroxyl group of the carboxylic acid, making a leaving group. 4. The alcohol oxygen, because its lone pair makes it a lewis base, and it attacks the carbonyl carbon 5. An ester |
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Nucleophilic addition of amine to aldehyde or ketone
1. reaction conditions 2. product 3. tautomerization? |
1. Acidic. The acidic protons protonate the carbonyl oxygen twice to form water as a leaving group.
2. Imine 3. A hydrogen from alpha carbon jumps to the nitrogen, forming an enamine. |
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Nitriles
1. What is it 2. If it is hydrolyzed in acid, it gives... 3. If it is reduced, it gives... |
1. C triple bond N
2. Carboxylic Acid 3. Amines |
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Order of acidity for functional groups from weakest to strongest
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1. Alkane
2. Alkene 3. H2 4. NH3 5. Alkyne 6. Aldehyde/Ketone 7. Alcohol 8. water 9. carboxylic acid |
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When fatty acids are oxidized, what is produced?
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1 NADH
1 FADH2 1 Turn of krebs cycle |
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One turn of krebs cycle yields:
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3 NADH
1 FADH 1 GTP |
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Isoelectric point:
1. What is pI? 2. What is the charge on an amino acid when the pH is less than its pI? 3. What is the charge on an amino acid when the pH is more than its pI? |
1. The pH at which the amino acid is a zwitterion, or has a + and - charge
2. It has a net positive charge. The acidic environment keeps all groups protonated. 3. It has a net negative charge. The basic environment deprotonates all groups. |
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What kind of anomer is glucose if hydroxyl group on highest numbered chiral carbon is the left?
...is to the right? |
L anomer
D anomer UPPERCASE LETTERS! Nothing to do with observed rotation. |
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NMR
1. What must the atomic number be? 2. What does this number do? 3. What does a NMR machine do? 4. When is resonance observed? 5. What is the calibration chemical? |
1. odd
2. creates a magnetic field around the nucleus 3. applies a variable external magnetic field, with a photon source that has a constant frequency 4. When photon has frequency that matches energy difference between low energy and high energy spin states. 5. TMS - tetramethylsilate |
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How does C13 NMR relate to proton NMR?
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The same thing, except no signal splitting is observed.
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The higher the Rf factor...
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The more the substance travels with the mobile phase.
ratio of component over solvent front |
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Distillation
1. Separates mixtures on basis of 2. What is the boiling point of a mixture? 3. What can make number two wrong? |
1. boiling point
2. the boiling point of the compound with the lowest boiling point 3. if the mixture is an azeotrope, or a mixture with a boiling point other than the boiling point of the compound with the lowest boiling point |
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Extraction
1. What two layers are initially present 2. What group is extracted first and how 3. what group is extracted next and how 4. what group is extracted next and how |
1. Aqueous and organic
2. The bases are extracted first by adding acid, shaking vigorously, protonating the bases, and extracting the aqueous 3. strong acids are taken next, by adding weak bases, which deprotonates the strong acids, adds them to the aqueous layer, and then they are extracted 4. weak acids are removed by adding strong bases. same as above. |
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Resonance structures:
What are they, really? Is a resonance structure ever really a true molecule? |
They are structures that collectively resemble what the molecule really is. They are used in cases of electron delocalization.
NO. It is just something that describes partly what the molecule is. |
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EAS:
Halogenation 1. Adding what to an aromatic ring? 2. What is the catalyst? |
1. Br or Cl
2. Lewis Acid, like FeCl3, FeBr3, AlBr3, or AlCl3, and heat |
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EAS:
Sulfonation 1. Adding what to an aromatic ring? 2. Reaction ingredients |
1. Sulfonic Acid
2. SO3 / H2SO4 |
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EAS:
Nitration 1. Adding what to an aromatic ring? 2. Reaction ingredients 3. What does this combination of ingredients do? 4. What is the final product? |
1. Nitro group
2. H2SO4 / HNO3 3. Produces nitro group, a really good electrophile 4. An aromatic nitro compound, the least reactive aromatic compound |
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EAS:
Acylation (Friedel-Crafts Reactions) 1. Adding what to an aromatic ring? 2. What are the reaction ingredients? |
1. An acyl group
2. AlCl3 (any lewis acid) creates a fine electrophile of the acyl group |
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Catalytic Reduction of Benzene:
1. What happens? 2. What are the reaction conditions? |
1. The benzene ring loses all its double bonds to become cyclohexane.
2. H2, Rh/C, 100 degrees celcius |
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What happens when you reduce an ester?
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Two alcohols are formed.
LiAlH4 can do this |
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Reducing agents and what they do
1. LiAlH4 2. NaBH4 |
1. Strong reducing agent - converts carboxylic acids, esters, aldehydes, ketones into corresponding alcohols. Converts Amide, Nitro, Azine compounds into amines.
2. Mild reducing agent. Reduces ketones and aldehydes to alcohols. Will not reduce carboxylic acids, esters, or amides. |
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Oxidizing agents and what they do
1. Tollens reagent |
1. Ag(NH3)2, used to test for aldehydes. Will oxidize aldehydes to carboxylic acids.
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