Alkane and Alkyne Addition Reactions

list the groups added, regioselectivity, and stereospecificity for: hydrohalogenation

• H + X (Cl, Br, I)

• Markovnikov (antimarkovnikov if ROOR is present)

• None

list the groups added, regioselectivity, and stereospecificity for: Acid Catalyzed Hydration

• H + OH

• markovnikov

• none

list the groups added, regioselectivity, and stereospecificity for: Oxymercuration-demurcuration

• H + OH

• markovnikov

• anti

*never has carbocation rearrangement

list the groups added, regioselectivity, and stereospecificity for: Hydroboration oxidation

• H + OH

• antimarkovnikov

• syn

list the groups added, regioselectivity, and stereospecificity for: Acid-catalyzed alcohol addition

• H + OR (commonly O connected to CH3)

• Markovnikov

• none

list the groups added, regioselectivity, and stereospecificity for: catalytic hydrogenation

• H2/catalyst (Pd, Pt, Ni)

• n/a

• syn

list the groups added, regioselectivity, and stereospecificity for: halogenation

• Br/inert solvent (CCl4, CH2Cl2)

• N/a

• anti

list the groups added, regioselectivity, and stereospecificity for: Halohydrin Formation

• X2 (CL2, Br2, I2)/ H2O or ROH

• markovnikov

• anti

list the groups added, regioselectivity, and stereospecificity for: Epoxidation

• O

• n/a

• syn

list the groups added, regioselectivity, and stereospecificity for: Anti-dihydroxylation

• OH + OH

• n/a

• anti

list the groups added, regioselectivity, and stereospecificity for: Syn Dihydroxylation

• OH + OH

• n/a

• syn

list the groups for: ozonolysis

if reduction (CH2s, DMS, Zn, H2O). Then a ketone (double bond O) and an aldehyde (double bond O with H attached) will be added

if oxidation (H2O2), then a ketone and carboxylic acid will be added

name the type of alkene addition that is occurring

Hydroboration oxidation

name the type of alkene addition that is occurring

hydrohalogenation

name the type of alkene addition that is occurring

ozonolysis w/ reduction

name the type of alkene addition that is occurring

catalytic hydration

name the type of alkene addition that is occurring

syn-dihydroxylation

name the type of alkene addition that is occurring

halohydrin formation

name the type of alkene addition that is occurring

anti-dihydroxylation

name the type of alkene addition that is occurring

acid-catalyzed hydration

name the type of alkene addition that is occurring

epoxide

Z or E

E

Z or E

Z

Z or E

Z

E or Z

E

when eliminating a geminal or vicinal dihalide to make an alkyne, what reagents can we use

1. excess NaNH2

2. H2O

when reducing an alkyne vis hydrogen addition, what reagents will be used to get an alkane, cis alkene, and trans alkene

alkane = H2/PD, Pt or Ni

cis alkene = H2 and Lindlar’s

trans alkene = Na and NH3(l)

what is the difference between these 2 hydrohalogenation reactions

the first is markovnikov and the second is anti markovnikov since it was treated with ROOR

in 1 eq BR2 (halogenation reaction), is the major product cis or trans

trans

when given a terminal alkyne, what kind reagents can be used to result in a markovnikov addition of a ketone

HgSO4 and H2SO4 - acid catalyzed hydration

if Sia2BH * THF and H2O2 NaOH was used on a terminal alkyne (hydroboration oxidation), what would the product yield

Aldehyde will be added via anti markovnikov

if we were to do a hydration reaction on an internal alkyne, what would the resulting structure be

we would get 2 possible ketone products - there is no markovnikov

what is the difference between oznolysis of an internal vs terminal alkyne

internal results in 2 carboxylic acids, while terminal alkynes will result in 1 carboxylic acid and CO2

what reagent do we use for alkylation synthesis

NaNH2 and it will add a carbon cain via SN2