Orgo Reactions & Mechanisms

How many intermediates does HX addition have?

1 or 2 depending on hydride or methyl shift

How many intermediates does Acid Catalyzed Alcohol (Or ether) addition have (e.g H2SO4, H2O)?

Depending on hydride or methyl shift or not, 1 or 2

How many intermediates does Halohydrin Addition have (Br2 MeOH)?

1 likely

How many intermediates does X2 Addition have?

1

How many intermediates does Hydroboration Oxidation have (1. BH3 THF, 2. H2O2 OH-)?

Depends on number of hydride or methyl shifts, likely 1

How many intermediates does Epoxidation have?

1

How many intermediates does Ozonolysis have?

1

How many intermediates does Catalytic Hydrogenation have (e.g H2, Pd/C)?

1

HX Addition:
Does Markovnikov’s rule apply, anti or N/A?
Is there a possible hydride or methyl shift?
Is it syn, anti, both, or N/A?
Racemic products (+/-) or no (+/-)?

Mark applies

Possible Shift

N/A

Racemic products if base is chiral, not racemic if achiral base

Acid Catalyzed Alcohol (or Ether, or water) Addition (H2SO4, MeOH or H2O)
Does Markovnikov’s rule apply, anti or N/A?
Is there a possible hydride or methyl shift?
Is it syn, anti, both, or N/A?
Racemic products (+/-) or no (+/-)?

Mark applies

Possible Shift

Anti and Syn

Anti racemic and syn racemic

Halohydrin Addition (Br2, MeOH)
Does Markovnikov’s rule apply, anti or N/A?
Is there a possible hydride or methyl shift?
Is it syn, anti, both, or N/A?
Racemic products (+/-) or no (+/-)?

Mark applies

Possible Shift

Anti racemic

Racemic products

X2 Addition:
Does Markovnikov’s rule apply, anti or N/A?
Is there a possible hydride or methyl shift?
Is it syn, anti, both, or N/A?
Racemic products (+/-) or no (+/-)?

Mark N/A

Possible Shift

SYN & ANTI

Racemic products

Hydroboration Oxidation (1. BH3 THF, 2. H2O2, OH-, HOH-):

Does Markovnikov’s rule apply, anti or N/A?
Is there a possible hydride or methyl shift?
Is it syn, anti, both, or N/A?
Racemic products (+/-) or no (+/-)?

ANTI MARK

Possible Shift

SYN ONLY

Racemic products

Epoxidation:
Does Markovnikov’s rule apply, anti or N/A?
Is there a possible hydride or methyl shift?
Is it syn, anti, both, or N/A?
Racemic products (+/-) or no (+/-)?

Mark N/A

Possible Shift

SYN ONLY

Racemic products

Ozonolysis:
Does Markovnikov’s rule apply, anti or N/A?
Is there a possible hydride or methyl shift?
Is it syn, anti, both, or N/A?
Racemic products (+/-) or no (+/-)?

Break that shit up and add carbonyl

Catalytic Addition of Hydrogen (H2, Pd/C):
Does Markovnikov’s rule apply, anti or N/A?
Is there a possible hydride or methyl shift?
Is it syn, anti, both, or N/A?
Racemic products (+/-) or no (+/-)?

Mark NOT APPLICABLE

Possible Shift

SYN

NO RACEMATES