MCAT – Orgo – Flashcards
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Unlock answersWhat do these prefixes describe? Vinyl Allyl Methylene |
Vinyl= monosubstituted ethylenes (vinyl chloride= CH2=CHCl)
Allyl= C3 substituted propylene (allyl bromide= CH2=CHCH2Br)
Methylene= -CH2 group (methylene cyclohexane= a cyclohexane with a CH2 group...double bond from cyclic C to a CH2)
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Name these common substituents 1. CH3 2. CH3 3. CH3 | | | H3C-C- H3C-C-CH2- HC- | | | CH3 CH3 CH3 4. CH3 5. CH3 | | CH3-CH2-CH- CH3-CH-CH2- |
1. t-butyl (tert-butyl) 2. neopentyl 3. isopropyl 4. sec-butyl 5. isobutyl |
Common names for ethene and ethyne.
When naming a molecule with both a double and triple bond in it, which gets the lower carbon number? |
Ethene= ethylene Ethyne= acetylene
When both in the same molecule, the double bond gets the lower number CH3CH=CH-C=C-CH3 2-hexen-4-yne |
What is a vicinal? What is a geminal?
Why are geminals/hydrates not often seen? |
Vicinals= diols with hydroxyl groups on adjacent carbons Geminal aka hydrates= diols with hydroxyl groups on the same carbon
Geminals/hydrates not often seen because they spontaneously lose water and produce carbonyls. |
What is an ether?
What is a 3-membered cyclic ether called?
Common names for: methanal ethanal propanal |
Ether= R-O-R
3-membered cyclic ethers= oxiranes or epoxides - or ethylene oxide
Methanal= Formaldehyde Ethanal= Acetaldehyde Propanal= Propionaldehyde |
Common names for: 2-propanone methanoic acid ethanoic acid propanoic acid |
2-propanone= acetone methanoic acid= formic acid ethanoic acid= acetic acid propanoic acid= propionic acid |
Prefix and suffix for: esters acyl halides amides nitriles/cyanide thiols imines ethers ...and just prefixes for: sulfides nitros azides diazos |
Prefix: Suffix: Esters alkoxycarbonyl- -oate Acyl halides halocarbonyl- -oyl halide Amides amido- -amide Nitriles/Cyanide cyano- -nitrile Thiols (RSH) sulfhydryl- -thiol Imines (R2C=NR'); imino- ; ; ; ; ; ; ; -imine Ethers ; ; ; ; ;;;;;; alkoxy-;;;;;;;;;;;;;;;;; -ether Sulfide (R2S) ; ;; alkothio- ; ; ; Nitros (RNO2) ; ;;;; nitro- Azides (RN3) ; ; ;;; azido- Diazo (RN2+) ; ; ;;; diazo- ; ; ; |
What are structural/confirmational isomers? ; What are enantiomers? ; ; |
Structure/confirmational isomers only share a molecular formula. ; Enantiomers are chiral objects that are nonsuperimposable mirror images. |
Put the following bases in order from strongest to weakest: RCO2-, ROH, HO-, RO-, H2O ; Put the following nucleophiles in order from strongest to weakest when in a protic solvent: CN-, HO-, Br-, I-, F-, H2O, Cl-, RO- ; Put the following nucleophiles in order from strongest to weakest in when in an aprotic solvent: Cl-, Br-, F-, I- ; Put the following leaving groups in order of best to worst: Cl-, Br-, F-, I- |
Base Strength: RO-;OH-;RCO2-;ROH;H2O ; Nucleophile strength in a protic solvent (larger atoms=stronger Nu in protic solvents: CN-;I-;RO-;HO-;Br-;Cl-;F-;H2O ; Nucleophile strength in an aprotic solvent (strong bases=stronger; Nu in aprotic solvents): ;F-;Cl-;Br-;I- ; Leaving group strength (weak base=better LG): I-;Br-;Cl-;F- ; |
Are SN1 and SN2 reactions favored in protic or aprotic solvents? ; What happens to the stereochemistry of SN1 and SN2 reactions? |
SN1 reactions are favored in polar protic solvents. SN2 reactions are favored in polar aprotic solvents. ; If the reactant is optically active, SN1 reactions produce racemic mixtures. If the reactant is optically active, SN2 reactions produce a product with an inversion of stereochemistry (still optically active). |
As you increase branching, what happens to the boiling point and density? As molecular weight increases, what happens to the melting and boiling points and density? |
More branching means decreased boiling point and decreased density (decrease the surface area so decrease intermolecular forces). As molecular weight increases, melting and boiling points also increase and density increases. |
Addition of cold, dilute KMnO4 to an alkene yields... ; Addition of hot, basic KMnO4 to a non-terminal alkene... |
Addn of cold, dilute KMnO4 to an alkene yields a 1,2 diol (vicinal diol/glycol), syn orientation. ; Addn of hot, basic KMnO4 cleaves the non-terminal alkene to produce a carboxylic acid and carbon dioxide...if the double bonded carbon is disubstituted, it produces a ketone. |
Steps for the addition of HX to an alkene. ; Steps for the addition of X2 to an alkene. |
Addition of HX to an alkene: step 1: Addn of H+ to less highly substituted C to form a stable C+ (Markovnikov's) step 2: Addn of halide to the positive C
Addition of X2 to an alkene: step 1: double bond displaces X- and forms a cyclic halonium ion step 2: X- attacks to form a dihalide compound in anti addition. |
Steps for addition of H2O to an alkene.
Steps for addition of a free radical (such as Br) to an alkene/alkyne. |
Addition of H2O to an alkene: step 1: potonation of the double bond (Markovnikov's) to form a stable C+ step 2: addn of H2O to positively charged C step 3: loss of H+ to form an alcohol; ; Addition of a free radical to an alkene: step 1: addn of the free radical to the less substituted C (anti-Markovnikov b/c adds H second) step 2: addn of H to the free radical C |
Steps of hydroboration and what it produces. ; Products of ozonolysis with Zn/H2O. ; Products of ozonolysis with NaBH4/CH3OH. |
Hydroboration: step 1: B attaches to the less sterically hindered C (anti-Markovnikov b/c H adds second) step 2: oxidation-hydrolysis with peroxide and an aqueous base (replacement of BH3 with OH) ...produces an alcohol in an anti-Markovnikov fasion with syn addition (of H and OH). ; Ozonolysis with Zn/H2O cleaves the double bond to form carbonyls (aldehydes or ketones...not carboxylic acids). ; Ozonolysis with NaBH4/CH3OH produces alcohols. |
What do peroxycarboxylic acids (such as CH3CO3H and mcpba) do to alkenes? What is the product? ; Polymerization occurs under... ; How does the boiling point compare between internal alkenes/alkynes and terminal alkenes/alkynes? |
Peroxycarboxylic acids oxidize alkenes and produce oxiranes. ; Polymerization occurs under high temperatures and high pressures. ; Internal alkenes/alkynes boil at higher temps than terminal alkenes/alkynes. |
| Elimination of 2HX's from a vicinal dihalide to form an alkyne requires... |
| Elimination of 2HX's for a vicinal dihalide to form an alkyne requires high temps and a strong base. |
| Difference between constitutional and conformational isomers. |
Constitutional isomers= different atom connectivity Conformational isomers= different 3D arrangement |
What are the structures of the following amine compounds: Amide ;Carbamate/Urethane Isocyanate Enamine Imine Nitrile/Cyanide Nitro Diazo Azide |
Amide:; O;;;;;; (carboxyl + amine) ; ; ; ; ;;; || ;;;;;;;;; RCNR2 ; ; ;; Carbamate/Urethane: ; O;;;;; (Ester + amine) ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ;;; || ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ROCNR2 Isocyanate: ;; R=O=C=NR; (add alcohol-;carbamate) Enamine: ; R2=CRNR2 (amine equivalent of anenol) Imine:; R2C=NR; (carbon=nitrogen) Nitrile/Cyanide:; C=N; (C triple bonded to N) Nitro: -NO2 Diazo: R2C=N=N; (N2 group) Azide: R-N=N=N; (N3 group) ; ; ; |
alkyl halide + ammonia -;....+base-; (CH3Br + NH3 -;_____+NaOH-;_____) |
Alkyl halide + ammonia -; alkylammonium halide salt alkylammonium halide salt + base -; alkyl amine CH3Br+NH3-; CH3NH3+Br-+NaOH-; CH3NH2 + NaBr +H2O |
What is Markovnikov's Rule?
What conditions often cause free radical addition? |
Markovnikov's= When adding a protic acid HX to a double bond, the H will add to the less substituted carbon, and the X will add to the more substituted carbon after. ; Peroxides, oxygen, and UV light cause free radical addition (which is anti-markovnikov...free radical adds before the free H). |
How can you form an amine from a nitro compound? ; How can you form an amine from a nitrile? ; How can you form an amine from an imine? |
Nitro compound + reducing agent such as Zn or Fe in dilute HCl turns the nitro group into a primary amine. ; Nitrile compound + hydrogen and a catalyst or LAH creates a primary amine CH3CH2C=N + LAH -; CH3CH2CH2NH2 ; Aldehyde or ketone + ammonia -; Imine Imine + hydrogen and a catalyst -; amine ; O;;;;;;;;;;;;;;;;;;;;; NH;;;;;;;;;;;;;;;;;;;;;;;;;;;;; NH2 ; ||;; +; NH3 -; ||;; + H2-Ni/RaneyNi -;; | RCR ;;;;;;;;;;;;; RCR;;;;;;;;;;;;;;;;;;;;;;;;;;;; RCR |
What is Zaitsev's Rule?
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| Zaitsev's rule states that if an elimination reaction can produce two products, the more highly substituted double bond will be the major product. |
Describe the frequencies these bonds would absorb in an IR spectrum: Carbonyl; (C=O) Alcohol or Acid (O-H) Amine (N-H) |
Carbonyl (C=O) ~1750 ;Alcohol or Acid (O-H) ~3000 (broad) Amine (N-H) ~3000 (sharp) |
| How can you form an amine from an amide? |
Amide + LAH -; amine ; O ; ||;;;; +; LAH -; RCNH2;;;;;;;;;;;;;; RCNH2 |
