Chapter 18 Flashcards
What is the mechanism for nucleophilic addition under basic conditions?
What is the mechanism for nucelophilic addition under acidic conditions?
Give the reagents necessary to transform each of the following starting materials
into 2-phenylethan-1-ol.
(Ph)CH=CH2
Give the reagents necessary to transform each of the following starting materials
into 2-phenylethan-1-ol.
- LiAlH4
- H3O+
Give the reagents necessary to transform each of the following starting materials
into 2-phenylethan-1-ol.
Bromobenzene
- Mg, Et2O
- Ethylene oxide (epoxide)
- H3O
Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.
2-Heptanol
Note: You can make the necessary epoxide by dehydration of propanol followed by oxidation with m-CPBA.
Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.
1-Butanethiol
Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.
2-Hexanol
Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.
** 2-Hexanone - CH3CO(CH2)3CH3**
- PBr3
- Mg, Et2O
- Acetaldehyde
- H3O+
- CrO3, aq. H2SO4
Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.
2-Methyl-1,2-propanediol
Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.
2,2-Dimethylpropanal - (CH3)3CCHO
Propose syntheses of the following compounds starting from alcohols with 4
carbons or less.
Hexanoic acid - CH3(CH2)4CO2H
Dess Martin Reaction (Periodinane)
Give reagents that accomplish the following transformation.
- PBr3
- ((CH3)2CH)2CuLi Gilman reagent
Give reagents that accomplish the following transformation.
- H2, Lindlar’s Catalyst
- O3; Zn, H3O+
Give reagents that accomplish the following transformation.
- BH3, THF
- H2O2, aq. NaOH
- NaH
- CH3CH2CH2Br
Give reagents that accomplish the following transformation.
- NaOtBu, tBuOH
- mCPBA
- NaOMe, MeOH
- NaH; MeI
What happens when you react TMSO with PCC?
Compound A is oxidized using PCC and then reacted with methyl magnesium bromide,
CH3MgBr, to form Compound B.
http://pages.towson.edu/jdiscord/www/332_answer_keys/Chapters_17_and_19/PracticeExam1AnsKey.pdf
What are the reagents used to protect an alcohol before reacting Grignards?
How do you unprotect it after the reaction?
Protect with: 1. Me3SiCl, Et3N
De-protection: H3O+
How do you reduce a ketone or aldehyde into an alkane?
(Clemmenson Reaction)
Zn(Hg)/
HCl, H2O
What is the product?
What is the mechanism for cis diol formation from and alkene?
What is the reagent for cleaving an expoxide to yield trans diols?
What reagents cleave an epoxide to yield cis diols?
How do you reduce esters to alcohols?
How do you add Br to the benzylic position a the end of CH3 in Ph-CH3?
Claisen rearrangement followed by Diels-Alder
Tautomerization of the Claisen product to a phenol does not take place because no H is available to dontate to the Oxygen.
