Organic Chemistry Reactions 2 Flashcards

Terms Definitions
Threonine
Lysine
Combustion
Phenol Synthesis
Sn1 Reaction
Simmons-Smith Reaction
(R,R)C=C(R,R)+CH2I2--Zn(Cu)/Ether-->(R,R)H-C-C(H2)-C-X(R,R)
Ozonolysis of Alkyne
t-butyl Ether
CF3CO2H ---> alcohols
Aromatics
HNO3/H2SO4 ---> nitrated aromatic
Fischer to Haworth projection.
secondary alcohol
Grignard + aldehyde
Hydroxylation by Acid-Catalyzed Epoxide Hydrolysis
(R,R)-C-O-C-(R,R)--H3O+-->(R,R)HO-C-C-OH(R,R)
What is the product?
What is the mechanism?
Alkoxide and Alkyl Halide
---> ethers
What is a Diels-Alder Reaction?
...
NaX, acetone
dehydrohalogenation of vicinal dibromides
Kolbe carboxylation
Reactants: Phenol, CO2
Products: Salicylic acid
1. NaOH, H2O
2. CO2, H2O
3. HCl, H2O
Amide
a. LAH b. H30+ ---> amine
Fractional distillation
Repeated distillations on inert objects like glass beads that help separate two liquids with boiling points less than 25 C apart.
Reduction of acyl halide?
H₂ Pd/BaSO₄ Quinoline
Oxidation of phenol
Reactants: Phenol
Products: Quinone (1,4-Benzoquinone)
1. K2Cr2O7, H2SO4
What is the preferred synthesis method?
Alkene
KMnO4, NaOH OR OsO4 ---> cis-1,2 diols
Electron withdrawing vs donating...what do each do to a negative charge and acidity?
Withdrawing delocalize/stabillize the negative charge (spread it over the molecule) which increase acidity. Donating do the opposite.
O3, DMS
ozonolysis to make ketones and aldehydes from alkenes
Friedel Crafts Reactions
set of electrophilic aromatic substitution reactions, alkylation involves the alkylation of an aromatic ring with an alkyl halide using a strong Lewis acid catalyst, acylation of aromatic rings with an acyl chloride using a strong Lewis acid catalyst
Saponification
ester + inorganic base-> alcohol + soap
Ethylene Oxide
a. RMgBr/ether b. H30+ ---> 1° Alcohol w/ 2 C'
What is a better nucleophile I or F?
Flourine
epoxidation
formation of a cyclic ether with three ring atoms, made by treating alkenes with peroxide-containing reagents, like m-CPBA, or using HOCl/KOH via inversion
1,2 Dihydroxylation
Reaction conditions: (1) OsO4 (2) aq. NaHSO3
Syn addition of 2 OH groups
2 Oxygens from OsO4 are added and cleaved and then hydrolyzed with NaHSO3
Things that can make an aldehyde
terminal alkyne (hydroboration-oxidation, then tautomerization)
alkene (oxidative cleavage with Zn or CH3SCH3)
primary alcohol (oxidation with PCC)
1° or 2° Alcohol
isobutylene gas, acid catalyst ---> t-butyl ether
What are the reagents for Clemmensen Reduction?
Hg(Zn) and HCl
Mitsunobu Reaction
converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine and diethyl azodicarboxylate (DEAD).[1] The alcohol undergoes an inversion of stereochemistry.
Making an alkane from an alkyl halide
Reduction with LiAlH4
Fermentation
a process in which an agent causes an organic substance to break down into simpler substances
Where do you start numbering a carbohydrate?
On the carbonyl end.
tertiary alcohol with two identical groups
2 Grignard + acid chloride
2' alcohol to ketone
Reaction condition: PCC in CH2Cl2, or H2CrO4 in acetone
or KMnO4 in OH-/H2O
Mechanism of hydroboration-oxidation
1) The pi bond electrons attack the boron of BH3 while the sigma B-H bond electrons attack the other carbon. The C-C double bond and the B-H bond are broken as the C-H and C-B bonds form. This rectangular transition state results in syn addition, with the BH2 on the less substituted carbon (anti-Markovnikov).
2) Hydrogen peroxide and -OH oxidized the alkylborane, replacing BH2 with OH.
Note: with an alkene, this is the end; with an alkyne, this then tautomerizes
Methyl, 1° or 2° Alkyl Halide
good nucleohile ---> Inversion of Configuration
The difference between oligo and polysaccharide?
Oligo is short poly is long.
Aldehyde + 1⁰ Amine =
An aldehyde reacts with a primary amine to produce an imine
Aldehyde + 1⁰ Amine --> Imine
1' and 2' alcohols to alkyl halides
Reaction conditions: PBr3 or SOCl2
Oxygen of hydroxyl group reacts with PBr2 and a Br- leaves, the Br- then attacks the C group so that a good leaving group of PBr2OH can leave
Oxygen of the hydroxyl group attaches to the sulfur of SOCl2 creating a complex in which eventually a Cl- group leaves and then extracts an H+ from the protonated O giving us HCl and resulting in a good leaving group of SO2Cl attached which leaves when a Cl- attacks
Making an epoxide from an alkene
Epoxidation with mCPBA or other peroxyacids (RCO3H)
Making an alcohol from an epoxide
Reduction with LiAlH4 (at less substituted carbon: Markovnikov)
Things to know about titration of amino acids...
1.Buffering capacity is greatest at the Ka's
2. Two moles of base need to be added in order to deprotonate one mole of most a.a.
3. When adding base, the carboxyl group looses the H first.
4. Titrations can be done in reverse starting with a basic solution and adding acid.
Ester + (2x) Grignard Reagent =
An ester reacts with a Grignard reagent to produce a tertiary alcohol.
Ester + (2x) Grignard Reagent --> Tertiary Alcohol
opening of epoxides with strong nucleophiles (often bases)
Sn2
1) The nucleophile attacks at the less-substituted carbon because of sterics. The C-O electrons on that side revert to the O-
2) H20 protonates the O-
The product is an alcohol anti periplanar to the nucleophile group.
Conditions for the reaction of alkene + oxidising agent eg KMnO4. Product is a diol
Heat under reflux in alkaline solution
What is significant about the α hydrogens on a β-dicarboxylic acid?
They are very acidic due to stabalization!
Making an alcohol from an alkene (Markovnikov: hydrogen adds to less subst)
Hydration with H2SO4 and H2O (H2SO4 protonates H2O to make hydronium)
What is the purpose of Infrared (IR) spectroscopy?
Certain bonds absorb infrared light at different frequencies and this can then be measured through what is absorbed vs what is transmitted.
Used for FUNCTIONAL GROUP identification.
Is there a way to convert primary and secondary alkyl halides into carboxylic acids? Sure!!
nitrile formation followed by acid or base catalyzed hydrolysis.
Mechanism of oxidation of a primary alcohol to a carboxylic acid
1) It follows the same first steps as a secondary at first. Then, after becoming an aldehyde, it reacts with H2O to form a hydrate (C with two OH groups, one H group, and an R).
2) The same process occurs again: nucleophilic attack of the Cr of CrO3 by the OH oxygen, transfer of the hydrogen to the O- of CrO3, and deprotonation by H2O.
What kind of bond does Cellulose have vs Starch and glycogen?
BETA 1, 4 vs the ALPHA of starch and glycogen (some α 1,6 in there too!)
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