Quiz 1 Flashcards
What is the mechanism for adding a metal hydride (XH) to an alcohol
H attacks H which goes to O. O ends up attached to X creating an H2 byproduct
What is the mechanism for adding elemental X to an alcohol
X releases an electron which attacks H going to O. O is attached to X creating an H2 byproduct
What is the mechanism for adding HX to a primary alcohol and what type of rxn is it
H attacks O, X attacks postive O creating H2O byproduct and Cl taking the place of OH. Inversion may happen Sn2
What is the mechanism for adding HX to a secondary alcohol and what type of rxn is it
CH3-CH(OH)-CH-(CH3)2
H attacks O, carbocation is created, rearrangement if needed, X attacks postive charge. May create a racemic mixture and an enantiomer Sn1
What is the mechanism for adding HX to a tertiary alcohol and what type of rxn is it
(CH3)3-C-OH
H attacks O, carbocation is made, X attacks postive charge. May create a racemic mixture Sn1
What is the mechanism for reactions with PBR3 and Pry and what type of rxn is it
CH3-CH(OH)-CH2-CH3
O attacks PBR3 onto Br, adding PBR2 to O, Pry attacked H which attacks O, BR attacks C that O is on, creates an inversion and byproduct of OPBr2. Sn2
What is the result of a rxn with SOCl2 to an alcohol and what type of rxn is it
CH3-CH2(OH)-CH2-CH3
Cl is added where OH is in the opposite conformation. Sn2 makes an inversion
What is the structure of PBR3
3 BRs attached to P individually and a lp on P
What is the structure of Pryidine (Pyr)
ring with 3 double bonds and a N in place of a C
What is used for a dehydration rxn
heat and a strong acid catalyst
What is the mechanism for adding H2SO4 to a secondary alcohol and what type of rxn is it
CH3-CH(OH)-CH3
O on OH attacks H onto O os H2SO4, Protonation by bond going to O, O of H2O attacks H of adjacent bond onto bond making a double bond. E1
What is the mechanism for adding H2SO4 to a primary alcohol and what type of rxn is it
CH3-CH2-CH2-CH2-OH
OH attacks H onto O, rearrangement if needed, H2O attacks H onto bond, to make a double bond, produces a major and minor product. E1
What happens to the three types of alchols in an oxidation rxn
primarys become aldehydes onto carboxylic acid if water is present, secondary become ketones and tertiary has NR
What is the mechanism for adding DMP to an alcohol
CH3-CH(OH)-CH3
O attacks I of DMP which goes on to one OAc causing DMP (minus one AOc) to attach to O of alcohol, free OAc attacks H of postive O which moves to O, triethylamine attacks H of OAc which eventually goes to an OAc of I resulting in a ketone and DMP with one OAc
What is DMP
Cyclohexane ring attached to a cyclopentane ring that has an I in 1 attached it 3 OAcs, an O in 2 and a O double bonded to 3
