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61 Cards in this Set
- Front
- Back
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What is Lindlar's and What does it do?
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BaSO4 + Quinoline on Pd --> alkyne to alkene cis; acyl halide to aldehyde
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How are Anhydrides formed?
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Acyl Halide + Carboxylate Anion or heat 2 carboxylic acids
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How do you name a substituted amide?
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N-subalkane+amide
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Hoffman Rearrangement
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Reduction of Amide --> primary amine + loss of CO2
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Saponification
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Hydrolysis (in OH-) of triacylglyceride (ester) --> glycerol (alcohol) + fatty acids (carboxylate anions)
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Grignard + ester
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substitute twice (ketone more reactive than ester) --> primary alcohol
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Reduction of Ester
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LAH, NOT BaH4
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Gabriel Synthesis
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imide that's part of ring replaced by 2 O- on each end and primary amine
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only carb. Deriv that'll react spon is ___
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Acyl Halide
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order of reactivity of carb derivs (most to least)
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acyl halide, anhydride, ester/carboxylic acid, amide
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Amide + LAH --> ?
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primary amine (dehydration) - oxygen grabs the H-
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amine vs amino
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if compound as whole has OH or COOH in it
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how make amide?
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carboxylic acid + amine --> condensation to amide (SINGLE BOND) (imine = double bond)
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how do you make carbamate?
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isocyanate (H-N=C=O) + OR- --> H2N-COOR
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Azide
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contains N3 functionality (zwitterion) RN(-)-N(+)triplebondN
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Carbamate
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like amide but attached to ester
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Isocyanate
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R-N=C=O
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exhaustive methylation also called ____; mech is ____
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Hoffman elimination, methylate amine via alkyl halide -->NH3+R; elim a H to make x2 bond and kick off NH3 group
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boiling point of amine (qualitative)
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more than alkane, less than alcohol (N=less EN so less H+ bond)
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synthesis of amines
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reduction (metal + lots of H's) of nitro (with Zn + HCl) or of CN (with LAH) + other nitrogen containing groups; direct alkylation of ammonia
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Extraction
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separate 2 immiscible fluids, their dissolved particles based on dif sol in aq and organic solvents
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Distillation
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separate 2 miscible fluids thru dif in bp (dif in imf) (fractional, vaccuum, simple)
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Filtration
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separation of s + l
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Sublimation
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separate s based on vaporization ability; impurities usu don't sublime easily
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Centrifugation
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separates solids based on mass + density (esp organic, cellular molecs)
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Recrystalization - vary what?
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sep solids based on solubility at various T
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Electrophoresis
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separate molecs based on size and/or charge (pI, SDS)
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Chromatography
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uses stationary + mobile phase to separate based on polarity/size/charge
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Rf
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solute dist / solvent front dist (measure of how much solute moved)
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What is the fingerprint region?
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Bond vibrations, stretch, rotations
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IR requirements:
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bond dipole - assymetric molec
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IR ether number
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1100 cm-
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IR Amines peak
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sharp peak at 3300 (like alchol but sharp)
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NMR requirements:
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odd atomic number / mass number for nuclei
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NMR: Aldehyde, Carboxylic, Aromatic, Alkane, Alkenes, e-withdrawing groups
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9.5, 11, 7, 1, 4-6, 3-5
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Do OH H's show up in H NMR?
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Yes, if can exchange with water (~6) if not, couple like a normal H
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Spin Coupling / Decoupling
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13 C - coupled = split by H directly attached (no other C's or H's)
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Mass Spec requirements:
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only detects cations - ionize atoms + accel thru mag field; measure mass/charge to abundance
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UV Spec useful for:
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useful for X2 bonds and/or hetero atoms with lone pairs (put in UV light and measure wavelength/absorb)
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Products of making Acetyl CoA
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2 CO2, 2 NADH
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Products of Ox Phos
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34 ATP, 10 H20
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What effect do EN atoms have on H NMR?
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Shift Downfield (to the L)
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Alcohol, Vinyl ppm for H NMR?
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3-5, 5-6
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1200 peak in IR indicates?
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C-O bond (alcohol, ether, ester single bond)
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Where on IR do C-C bonds show up?
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Barely
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Basis for NMR
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nuclei absorbing radio waves + changing spin state
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Basis for UV spec
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e- absorb light E and jump to higher MO (antibonding), measure abs and color changes
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Basis for IR spec
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polar covalent bonds absorb IR light + vibrate with more E
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Will get same NMR signal if H are in same..
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chemical environment
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Why is measuring mass/charge important for Mass Spec?
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Polyatomic ions may be multicharged
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D vs L sugars differ at… and are …
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C furthest from ket/ald: R = D, L = L; also differ at every other stereogenic center - enantiomers!
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a vs b sugar; fixed?
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in cyclic hemiacetal form; b = up = equit; constantly interconvert thru mutarotation
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Fischer projection: right side OH = up/down on chair
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down! So anomeric OH is right = down = alpha (b/c down is always same and in type of chair we draw, it's axial)
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how do you form a glycosidic bond?
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hemiacetal, anomeric OH attacks C6 and w/ H+, kicks an H20 out so it's bonded via O and is now a full acetal
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B glycosidic linkages make: while a linkages make:
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chain (cellulose 1,4 B linkages), branches (glycogen + starch, 1,4 a and 1,6 branches)
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only form acetals at…
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anomeric C
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reducing sugar
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has OH at anomeric C1 carbon so in its free form, is ald or ket (taut to enol) and can be oxid to carb acid
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glycosidic linkages cause lack of ability to ___
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lack of mutarotation
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composition of fatty acid
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carboxylic head + long alkyl chain tail (phobic)
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composition of triacylglycerol
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esterification of glycerol: tri-alcohols + esters (involves dehydration)
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saponification
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opposite of making triacylglycerol; alkaline hydrolysis of triacylglycerol --> glycerol + carboxylic acids salts
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