Part 8 Flashcards
HCN + aldehydes or ketones –> ??
Aldehydes and ketones react with HCN to produce stable compounds called cyanohydrins. (CN and OH attached to same carbon group)
Aldehyde + Aldehyde + base –> ??
e.g. two acetaldehyde molecules + base –> ??
Aldol Condensation reaction:
Aldehyde acts as both nucleophile and target. This will create an aldol = aldehyde + alchohol.
Product: a beta-hydroxyaldehyde
Define spin splitting in HNMR?
If two magnetically different protons are within three bonds of each other a phenomenon known as coupling, or splitting occurs.
Note on E2 reactions regarding base used
Bulkyness of base affects the hydrogen attacked on species. Will attack less substituted if base is bulky.
If base is not bulky, then it will attack most substituted.
Concerted reaction
Chemical reaction in which all bond breaking and bond making occurs in a SINGLE step.
Which of the following would be the best solvent for an SN2 reaction?
a. H2O
b. CH3OH
c. CH3SOCH3
d. heptane
e. tosylate
c. CH3SOCH3 (dimethyl sulfoxide) gives best results if a polar aprotic solvent is used.
a and b are wrong because these are both polar.
D is a heptane and is incorect because it is a nonpolar solvent.
c. tosylate is a good leaving group not a solvent.
Combustion
Reaction of alkanes with molecular oxygen to form Carbon dioxide, water, and heat.
CH3COOH + CH3MgBr –> ??
CH3COO-
Grignard reagents normally convert esters and ketones to alcohols.
Williamson Ether Synthesis is an example of what type of reaction?
a. E2 or SN2
b. E2
c. SN2
d. E1 or SN1
e. two of the above
c. SN2
William Ether synthesis produces ethers from reaction of metal alkoxides with primary alkyl halides or tosylates. Via an SN2 reaction.
RCOOH + NaOH –> ??
RCOO-Na+ (a soap) + H2O
Peroxycarboxylic acids (mcpba or m-chloroperoxybenzoic acid)
Alkenes can be oxidized with mcpba. The products are formed are OXIRANES.
True or false: Phenol can exist as a very temporary and less stable keto form via tautomerizing?
TRUE
Ozonolysis
Reduction mechanism. Results in aldehydes or ketones depending on treatment.
Alkyne + O3 –>
Alkynes can be oxidatively cleaved with ozone to make 2M COOH.
Which reagent will give a CIS-product when reacted with an alkyne?
- H2, Pd/BaSO4, Quinoline (lindlar’s catalyst)
- a)BH3 b)CH3COOH
both produce cis products.