Final Flashcards
What is the mechanism for adding HCl to 2-methylcyclohexanol
O attacks H, making H2O which leaves, creating a cation, rearrangment occurs to methyl group, Cl- attacks cation creating enantiomers; molecules on opposite directions
What does PBr3 do to 3-methyl-2-butanol and what type of reaction is this
Add Br in the place of the alcohol but inverted; Sn2
What does HBR do to 3-methyl-2-butanol and what type of reaction is this
Rearrangement making 2-bromo,2-methylbutane; Sn1
What does adding CH2SO2CL and NaOMe do to 3-methyl-2-butanol and what type of reaction is this
E2 rxn where MsCl takes the place of OH and then be eliminated creating methyl-2-butene
What does adding 1.TsCl 2. Na+Ot-Bu- and 1.BH3, THF, 2.NaOH, H2O2 do to 3-methyl-2-butanol and what type of reaction is it
E2 reaction where OTs replaces alcohol with first reaction then NaOt-Bu make 3-methylbutene and 2nd reaction makes 3-methylbutanol
What is the starting product when (COCl)2, DMSO and Et2N are used to make 2-hydroxy-2-methyl-3-pentanone
propane with alcohol group on 2 and 3 and methyl group on 2
What are the reagents for swern oxidation and what does it do
(COCl)2, DMSO and Et3N and makes an alcohol into a double bond O but only non hindered ones
What does H2SO4 and heat do to a cyclohexane with a methyl,2-hydroxylpropane substituent
OH becomes water to make LG, cation rearranges then LG attacks to move H to make double bond
What does 1. OsO4 2. NaHSO3, H2O do to cyclohexane with methylpropene substituent
adds alcohol groups to either side of bond in same conformation; makes enatiomers
What does HIO4 do to cyclohexane with 1-hydroxy,1-methylpropane and OH substituents on the same carbon
break bond between the alcohol groups making separate molecules with double bond O
What does 1.Br2, H2O 2.NaH do to 2-phenyl,2-butene with methyls on the same side
First reaction adds OH to the more substitued side and Br to the least substituted side with the methyl groups being up and Ph and H down. Second reaction removes OH and Br and forms a bond between then with O
What does one eq of HCl do to a cyclohexane connected to O connected to tertbutyl
Breaks off t-Butyl to make alcohol group, then adds Cl to cation on t-Bu to make tert-butyl chloride and cyclohexanol
What does HCl do to 1,2-Dimethylcyclohexanol
Makes 1-chloro,1,2-dimethylcyclohexane with methyl groups up and Chloride down and its diastereomer (Cl up and its methyl group down)
What does 1. BH3, THF 2. H2O2, NaOH 3. CrO3, H2SO4, heat do to ethyli-2-denecyclopentane
The first two (really one rxn) adds H to the more substituted and OH to the least substituted side. The last rxn is a jones oxidation, turning the OH into a carb acid (COOH)
What does 1.HCO3H and 2.NaSH 3.H2O do to methylcyclohex-1-ene
First reaction turns the double bond into a O connected to both carbons (plus enantiomer) and second reaction causes SH to attack least substituted side of O making alcohol group down, methyl up, and SH up (plus enantiomer)
What does 1.NaH and 2.EtBr 3.HI (excess) do to methanol benzene
first reaction adds Et group to O and second reaction adds I where O is and makes EtI
What does 1.MsCl, Pry 2.NaBr do to 2-ethyl,2-methylcyclopentanol
First reaction adds Ms in place of H of alchol group. Second reaction adds Br in place of OMs but in the opposite conformation
What does H2SO4 and low heat do to cyclobutane methanol cyclobutane
Ether formation where 2 of cyclobutane methanol reacts to make cyclobutyl ether
What reagents are used to make bromo-cyclopentane into 2-chloro-cyclopentanol
Na+ O-Me and MeOH and heat to make a double bond betweent the first carbon and carbon that has Br. Then Cl2 and H2O to add Cl and OH
What is the mechanism for adding NaH to 2-chloro-cyclopentanol
H attacks H of OH making it negative, lp of O attacks C of Cl making it leave and adding another bond to O making it cyclic
What is the mechanism for adding one eq of HI to cyclohexane connected to O connected to propane
O attacks H onto I, O becomes lg making a cation on cyclohexane, I attacks cation creates Iodocyclohexane (enantiomer) and propanol
What does 1.Mg, ether 2.ethanal and H+ and H2O do to cyclopentene with a bromoethane subtituent
First reaction will add Mg to Br. Second reaction adds the ethanal but with the double bond O as an alcohol group
What does PhNhNH2, pH 6.5 and heat do to a cyclopentene with a methylpropane with a double bond O on the 2 carbon
Adds N-NH-Ph where O is, keeping the double bond
what does Zn(Hg), HCl, and heat do to molecule A and what is the reaction
Clemmensen reduction; removes ketone (double bond O)
What does heat do to molcule A and what is the reaction
Decarboxylation; removes carb acid to make cyclohexane with double bond and double bond O and CO2 (g)
What does 1.EtNH2, Ph 6.5 heat 2. NaBH3CN 3.H+, H2O do to molecule A and what is the reaction
reductive amination. First reaction adds =NEt in place of ketone. Second reaction replaces that with NHEt
What does Ph3PR do to molecule A and what is the reaction
Adds R in place of ketone; wittig reaction
What reagents can be used to replace the ketone of molecule A into an alcohol group
NaBH4 and H3O+
What is the initial molecule that can react with PCC to make pentanone
methylbutanol
What does 1.NaCN 2.H+, H2O do to pentanone
Turn the double bond O into an alcohol group and CN group
Question 1
Answer to the right
What reagent can be used to selectively reduce aldehydes and ketones
NaBH4
Draw 4-bromo,3-oxo pentanoic acid
See molecule D
Draw 3-methyl cyclopentanenitrile
See molecule E
Question 7
Answer to the right
Question 8
Answer to the right
What does Cl2 and H+ do to cyclopentanone
Cl is added as a substitute to an alpha carbon
What does heat and KOH do to 2-chlorocyclopentanone
OH attacks H on the carbon next to Cl onto Cl removing them and making a double bond
What does NaOH and excess I2 do to ethylanonecyclohexane
Replaces CH3 with O-Na+ and makes CHI3
What are activators of benzene rings
CH3, OH, NH2 and anything with lone pairs
What are deactivators of benzene rings
double and triple bond, halogens, and electronegative atoms
What addition is preferred for activators with benzene rings
para (across from atom) and ortho (right next to atom) (para more so)
What addition is preffered for deactivators with benzne rings
meta (H away from atom)
