Help
Options
Didn't know it?
click below
click below
Knew it?
click below
click below
Don't Know
Remaining cards (0)
Know
retry
shuffle
restart
0:00
Embed Code - If you would like this activity on your web page, copy the script below and paste it into your web page.
Normal Size Small Size show me how
Normal Size Small Size show me how
Orgo Errors
| Question | Answer |
|---|---|
| What is the bromine test? | Br2/CCl4 is reagent, tests are alkenes and alkynes, dissapearance of brown color (bromine) signifies positive result |
| The rules for aromaticity are as follows: | The compound must be cyclic. The ring must be fully conjugated and planar (none of the atoms can be sp3 hybridized). The system must satisfy Huckel’s rule (# of pi electrons = 4n + 2, where n is any integer). |
| Benzene is reacted with one equivalent of Cl2 and FeCl3. What is the major product of the reaction? | This reaction can be classified as an electrophilic aromatic substitution reaction, specifically the chlorination of benzene. So, just Cl will be on the benzene. |
| Antiaromatic | Cyclic, planar, fully conjugated, 4n π electrons |
| Non-aromatic | Fails one or more aromaticity requirements |
| How do ketones affect EAS reactions? | Ketones are electron-withdrawing groups due to the oxygen’s electronegativity. This electron withdrawal makes the aromatic ring less nucleophilic and less reactive in electrophilic aromatic substitution (EAS) reactions. |
| NBS | performs allylic bromination in the presence of heat or light. Allylic bromination is the replacement of a hydrogen atom on an allylic carbon (allylic = the carbon neighboring a C-C double bond) with a bromine atom |
| An oxygen atom with two single bonds and two lone pairs is usually | sp3 hybridized (because it has 4 electron domains). But the oxygen atom can be sp2 hybridized because one of its lone pairs is delocalized (with 3 electron domains). If it's near another oxygen, it can switch the double bond to |
| How to tell which hydrogen is the most shielded | The one near the triple bond (or highest bond, usually) |
| HgSO4, H2SO4, H2O as a reagent | Markovnikov addition of OH that turns to a ketone via enol intermediate |
| Which molecule has a strong peak at 1700 cm-1? | Carbonyls would have a strong peak around here, so look for those. |
| How many structural isomers does trichlorobenzene have? | 3, structural or constitutional isomers have the same molecular formula but a different arrangement of atoms. |
| haloform reaction (xs. NaOH, xs. Cl2) H3O+ | Creates a carboxylic acid + haloform (HCX3) |
| (COCl)2, CH3OH | Oxalyl chloride, (COCl)2, converts the carboxylic acid to an acid chloride. When the acid chloride is reacted with an alcohol, an ester is formed. |
| What happens when an acidic molecule interacts with a basic molecule? | A proton transfer will occur. Ammonia will deprotonate the carboxylic acid to form ammonium and a carboxylate ion. |
| A self-aldol condensation product of acetaldehyde contains which functional groups? | An alkene and an aldehyde |
| Which of the following compounds cannot form an enolate if treated with the necessary base? | A carbonyl can only be converted to an enol or enolate when it has one or more hydrogens on the alpha carbon. A SINGLE HYDROGEN WILL NOT WORK |
| If you have two cyclic ketones and you're trying to find where the double bond will go... | It should be adjacent (close) to the bottom one |
| Adding H3O+ and heat to a compound with three oxygens will... | remove two oxygens |
| Which of the following reagents/reactions below involve a 1,4 addition to an α,ß-unsaturated carbonyl? I. Grignard reagent II. Gilman reagent III. Lithium aluminum hydride | II only, Li[CuR_2] |
| If you want to turn a ketone into a carboxylic acid, you need... | BOTH NaOH and H3O+, along with the X2 |
| What does Cl2, CCl4 do and does it invert stereochemistry? | It adds two Cl's to both sides of the double bond and there's an inversion, so two different Cl2's |
| LDA Tip | It can commonly be used to make an alkene via E2 reactions |
| Which radical is capable of rearranging? | A radical can rearrange if it is adjacent to a double bond or a benzene ring, not an sp3 carbon |
| Which of the following compounds will only react as a dienophile (not a diene) in a Diels-Alder reaction? | The key to solving this question is determining which compound is only capable of reacting as a dienophile. A diene must have conjugated C-C pi bonds. If it does not have alternating double and single bonds, it won't work. |
| Which diene would react the fastest in a Diels-Alder reaction? | The diene in a Diels-Alder reaction must be conjugated (two alternating double bonds) and in the cis conformation (the two double bonds are on the same side of the single bond). |
| Diene | In order to be an effective diene, a molecule must have two double bonds separated by exactly one single bond (conjugated) and have the spatial freedom to bend into the required s-cis shape. |
| Dienophile | A dienophile must have at least one π bond (a double or triple bond). A carbonyl like an aldehyde will not work, nor Saturated compounds (no C=C or C≡C bond), e.g. ethane. Or strong alkenes or aromatic rings. |
| A chemist reacts 2-pentanol with chromic acid, the reagent used in the Jones Test. What is the expected IR absorption of the NEW functional group present after the reaction is complete? | 1700 cm-1, Recall that when primary or secondary alcohols are reacted with chromic acid, they’re oxidized into carboxylic acids or ketones, respectively. In our case, we have a secondary alcohol being oxidized into a ketone. |
| A mixture of methanol and 1-pentanol would be best separated by which of the following means? | distillation. Both molecules can hydrogen bond due to their OH groups, but 1-pentanol has a much higher boiling point because its longer hydrocarbon chain increases dispersion forces. |
| When a separatory funnel containing ethane, ethanoic acid, and dichloromethane has aqueous NaOH added, which layer does ethanoic acid migrate to? | When NaOH is added, it will deprotonate the ethanoic acid, making it soluble in the aqueous layer. When using organic solvents that contain Chlorine, the organic layer is denser and on the bottom of the funnel. |
| A mixture of benzoic acid and phenol is dissolved in diethyl ether. During an acid/base extraction, aqueous sodium hydroxide is added to the mixture. Will the extraction be successful? | No, benzoic acid and phenol will both reside in the aqueous layer. Hydroxide is a strong base and will deprotonate both phenol and benzoic acid. A weaker base like sodium bicarbonate could be used here, as benzoic acid is more acidic than phenol. |
| A mixture of phenol and a typical amine are dissolved in diethyl ether. During an acid/base extraction, aqueous sodium bicarbonate (NaHCO3) is added to the solution. Will the compounds be separable via this acid/base extraction? | No, the sodium bicarbonate will not deprotonate the phenol. Sodium bicarbonate is strong enough to deprotonate stronger acids such as carboxylic acids, but not phenol. |
| A chemist has a 50:50 liquid mixture of two unknown compounds in a beaker: compound A and compound B. He finds that compound B has a very low vapor pressure relative to compound A. What technique could the chemist use to separate the compounds? | Distillation. Recall that vapor pressure and boiling point have an inverse relationship to one another. As a compound’s boiling point increases, its vapor pressure subsequently decreases. |
| What's the C NMR for carboxylic acid? | 180, ketones and aldehydes are in the 200s |
| Which pair of molecules will result in a reaction that most strongly favors the products? | equilibrium always favors the formation of the weaker, more stable acid. Therefore, an acid-base reaction that has a strong acid in the reactants and a very weak acid in the products will strongly favor the formation of the products. |
| How many stereoisomers are possible for the following compound? | The maximum number of stereoisomers for any chiral compound is equal to 2^n with n being the number of chiral centers. |
| H2O, reflux | Because the reaction occurs in reflux (heat) conditions, elimination is preferred over substitution. The major product of the reaction is the more substituted Zaitsev alkene - including proton transfer if needed |
| 2-ethylpentanol vs. 2-ethylpentan-1-ol | 2-ethylpentan-1-ol, if there's the option |
| Which of the following molecules is most acidic? I3CCOOH or F3CCOOH? | F3CCOOH |
| All of the following techniques can be used to separate two liquids EXCEPT one. Which one is the EXCEPTION? Chromatography, Distillation, Extraction, Filtration, Centrifuge | Filtration, method of separation used to separate solids from liquids. |
| Which of the following carbocations is most stable? | vinyl/phenyl < methyl < 1° < 2° < 3° < allyl < benzyl |
| allyl | Next to the double bond, on a separate carbon |
| If one compound has two wedges and the other has two dashes, but their substituents are in the same spot, then | They are identical compounds |
| Tip about Unsaturation Formula | X only counts for halogens, so O wouldn't count |
| Which of the following solvents would favor an SN2 reaction over an SN1 reaction? | Acetone. Polar aprotic solvents such as acetone, DMSO, and tetrahydrofuran favor SN2 reactions over SN1 reactions because they make nucleophiles more reactive. |
| When you're pushing an arrow from somewhere to somewhere... | The place that the arrow is coming from is losing electrons, so it would be + while the place the arrow is going to would become - |
| CH4 would best dissolve in which of the following solvents? Water Carbon tetrachloride Acetone DMF Ammonia | Carbon tetrachloride, ammonia is a polar solvent while CCl4 is nonpolar, so it would work better |
| What is the product of the following reaction sequence? 1) Br2, hv 2) NaOET, heat 3) Br2, H2O | Anti addition of Br and OH, First step adds a Br, second adds a double bond, and third adds a Br and OH anti on each side of the double bond. OH group should add to the more substituted portion. |
| When might an obvious diastomer be identical? | You may be inclined to think the molecules are stereoisomers, but they are actually identical. The molecules are achiral because they do not contain any stereocenters. |
| H2O as a reagent with a tertiary halide? | shown is solvolysis, an SN1 reaction. The starting molecule is a tertiary alkyl halide, so a stable carbocation intermediate is formed via the loss of a bromide ion. |
| Which of the following correctly describes a kinetically favored product? | Lowest Energy Intermediate |
| Grigard Reagent on a Ester | Makes a tertiary alcohol, there should be no additional oxygens left afterwards |
| Which of the following compounds would undergo an E1 reaction most efficiently? | Remember that the best carbocation spot can still be a carbon connected to 4 different things. |
| H2NHH2 | Remember that this is Wolf Kishner and would turn a ketone into an alkane. |
| What does an intermediate of an electrophilic aromatic substitution reaction look like? | E attached, carbocation to the side of it, one of the pi bonds missing and the remaining ones are altered |
| How many resonance structures are possible for benzene? | 2 |
| Concentrated H2SO4 vs Dilute H2SO4 | Dilute can turn an alkene to an alcohol by adding an OH group by Mark addition, while the concentrated will turn an alcohol to an alkene |
| KOCH2CH3, HOCH2CH3 | KOCH2CH3 is a strong base and the reaction occurs in a polar protic solvent, so the E2 reaction is favored. An alkene would be added in place of whatever substituent is already there and it would have to be anti-periplanar so probably inversion. |
| Acyl chlorides react with alcohols to form... | esters |
| Which functional group is present in CH3OCH3, CH3CH2OCH3 and CH3CH2CH2OCH3? | Ether, remember that with ketones it looks like CO |
| 1) mCPBA 2) H3O+ | Makes epoxide and breaks open to leave two OH's anti |
| What is the hybridization state and bond angle of the indicated atom? O from OH in C6H5COOH | sp2, 120° The O would normally be sp3, but it can be delocalized by the double bond nearby. |
| When you're counting the amount of pi and sigma bonds, remember this! | Don't forget to include the invisible bonds to hydrogen for the sigma bonds. |
| If there's a choice between a ortho or para position, you would choice... | The para position, because it leads to less steric hindrance |
| Priority of Functional Groups | Carboxylic Acids → Sulfonic Acids → Esters → Acyl (Acid) Halides → Amides → Nitriles → Aldehydes → Ketones → Alcohols → Thiols → Amines → Alkenes → Alkynes → Alkanes & Ethers → Benzenes |
| When you're making a double bond, the arrow pushing mechanism should... | Point TOWARDS the place where the double bond will go |
| Where reagent serves as the catalyst for a carboxylic acid becoming an ester? Base Acid NaCl Grignard Reagent DMS | Acid |
| Cl2, H2O vs Cl2, AlCl3 vs Xs. Cl2 | First adds Cl and OH anti via mark addition, next adds just one Cl to make chlorobenzene, and last adds two Cl's cause it's excess |
| How to find the highest melting point | First see which has the strongest intermolecular forces, then amount of carbons. Having a larger molecular weight can also have an effect. Molecular symmetry also impacts melting points, but not really boiling points. |
| Which of the following compounds is insoluble in water at a neutral pH but is the most soluble at a low pH? C6H5OH CH3CH2CH2CH2COOH C6H5CH CH3COOCH3 C6H5NH2 | C6H5NH2. Phenol, benzaldehyde, and aniline are insoluble in water. Pentanoic acid has a hydrocarbon chain longer than 4 carbons, so it is insoluble as well. Methyl ethanoate is slightly soluble. However, aniline acts as a base at low pH. |
| Ketone + Methyl lithium (CH3Li) | Tertiary alcohol. This also happens with a Grignard Reagent, but with a Gilman reagent R₂CuLi, there would be no reaction! |
| 1) Hg(OAc)2, H2O 2) NaBH4, NaOH | used in oxymercuration-demercuration, which is used to convert an alkene into an alcohol by adding H and OH to the alkene Markovnikov style. |
| PCC | Can be used to turn an alcohol into an aldehyde OR ketone |
| When can a product be both thermodynamic and kinetic? | A product can be both kinetic (forms fastest) and thermodynamic (most stable) when the pathway with the lowest activation energy happens to lead to the most stable product. So less activation energy and less energy on the product. |
| What is the IUPAC name of the compound represented by the structural formula CH3COOCH2CH2CH3? | Propyl ethanoate. List the alkyl group bonded to the ester oxygen prior to the parent chain, with the suffix “yl” (in this case, propyl). |
| What's the lowest and the highest activating substituents? | NH2/NR2, NHR are the highest and R is the lowest |
| What's the lowest and the highest deactivating substituents? | CN, NO2, and NR3 are the highest and F/Cl/Br are the lowest (also ortho/para directing) |
| All of the following reactions will produce an alkene EXCEPT one. Which one is the EXCEPTION? Ozonolysis Alkyne reduction w elemental sodium and ammonia Wittig reaction Alkyl halide elimination Alkyne reduction w hydrogen and Lindlar’s catalyst | Ozonolysis. Ozonolysis of alkenes with a reductive workup produces aldehydes and ketones. Ozonolysis of alkenes with an oxidative workup produces carboxylic acids and ketones. |
| What is the major product of the following reaction? KOH added to a Br and OH with a gap in between? | SN2 reaction occurs. It would be E2 if dissolved in ethanol and methanol. So, the OH would be deprotonated and a cylic thing would form; the Br would also be removed. |
| Which of the following is the strongest base? CH4 H2O CH3OH N(CH3)3 NH4 | N(CH3)3 |
| What reagent is needed to convert CH3COOH to CH3COOCH3? | CH3OH/H2SO4 |
| Which of the following can be added to separate bromobenzene and propionic acid during an extraction? | NaOH |
| Tip about extra carbon | Usually when you attach something, there's going to be a carbon joining to the ring and then the rest of the line. |
| Diels-Alder vs. Dieckmann condensation | Dieckmann condensation typically turns a line into a ring, while Diels-Alder deals with double bonds and adds rings |
| How to determine whether it's a primary or secondary amine? | A primary amine is connected to one carbon, while a secondary amine is connected to two carbons. |
| Which of the following is the best eluent for column chromatography? | acetone is an excellent choice as it as a polar aprotic solvent that can effectively dissolve and elute moderately polar compounds. |
| What best describes the reaction shown below? HR, ROOR | Free radical addition. Not EAS, because those will always require benzene as a starting reactant. |
| Which reaction type can the opening of an epoxide by hydroxide be classified as? Reagents are NaOH, H2O | SN2 |
| Benzyl Carbocation Tip | Remember that's it's going to be on a carbon ATTACHED to the benzene, not directly on the benzene |
| Each of the following laboratory techniques can be used to separate an organic mixture EXCEPT one. Which one is the EXCEPTION? Filtration Gas chromatography Distillation Centrifuge Thin layer chromatography | Filtration |
| Sodium amide (NaNH2) | deprotonates the terminal alkyne to form an acetylide ion. You can then add R groups to the alkyne. But REMEMBER this will NOT produce an alkene. |
| In bromine vs. alkene, which would have the higher priority? | Alkene |
| Which would make the more acidic benzene? Attaching a F or a NO2? | Attaching the NO2, because it's the stronger electron withdrawing group. |
| NBS, hv Tip | It will be allylic or benzylic, meaning it won't directly be ON the double bond, but attached to it. |
| mCPBA | When making epoxides, take note of how many methyl groups or substituents are bonded to the carbon dieneophile. The carbon should also be in the same place. |
| Which of the following molecules has the lowest pKa? 4,4,4-triiodobutan-2-one vs. 1,1,1-trifluoropropanone | 1,1,1-trifluoropropanone |
| Benzene can be described as being which of the following? Lewis acid Lewis base Bronsted-Lowry base Bronsted-Lowry acid Arrhenius base | Lewis base. As an aromatic compound, benzene is a Lewis base because it donates one of its electron pairs in an electrophilic aromatic substitution reaction. |
| If the benzylic carbon of an alkylbenzene is bound to at least one hydrogen atom, treatment with KMnO4, OH– and H3O+ will result in oxidation to give... | carboxylic acid. The rest of the substituent will be cleaved. In this case, the product has two carboxyl groups, so there must be two benzylic carbons on the substrate. So if you see open carboxylic acids, you're looking for a blank space with hydrogens. |
| Radical arrow tip | When making a radical product, you would need the thin, fancy arrows. |
| What's the hybridization state and formal charge of a carbon attached to two hydrogens, one carbon, and one radical? | sp2, 0 Sp2 because it's technically attached to three things - not 4 - and 0, because the radical DOES count in diminishing its charge. |
| ROOR Tip | It will appear as H2O2 |
| Bicyclic vs spiro | Spiro compounds will be flat, bicyclic will be 3D |
| Between triple bonds, which would be more acidic? | The one that has a proton bound directly to a sp carbon, increasing the s character. |
| When you can tell an oznolysis reaction is reductive or oxidative? | DMS or Zn/HOAc vs H₂O₂. The former would be reductive |
| Benzyl vs Phenyl Substituent | A benzyl substituent has a CH2 included whereas a phenyl group is simply just a benzene ring. |
| Which of the following structures is NOT a resonance form of the molecule below? (Tip) | Figure out how much charge the original compound had and then add up the charges on the resonance structure to make sure it matches. If it doesn't match, it can't be a resonance. |
Created by:
smurtab