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Reactions Semester 1
Designed to test knowledge of reagents and basic regio/stereochemical attributes of reactions covered in a basic 1st semester organic chemistry course.
25
Organic Chemistry
Undergraduate 2
12/11/2012

Additional Organic Chemistry Flashcards

 


 

Cards

Term
Add Water to the Double Bond
Definition

1. Acid-catalyzed hydration (H2SO4) Trans, Mark

2. Hydroboration (BH3, then H2O2 and NaOH) Cis, Non-Mark

3. Oxymercuration (Hg(OAc)2, then NaBH4) Trans, Mark


KNOW THIS REACTION x3

Term
Form Ethylene Oxide (specific)
Definition
Use Ag catalyst and ethylene in air
Term
Halogenate (X2) the Triple Bond
Definition

Use 1 or 2 mol X2 and CH3COOH

If 1 mol, trans addition

Term
Convert an Alcohol to a Haloalkane
Definition

Use HX in water. If alcohol is 3o or 1o with beta branching, the intermediate is a carbocation. If the alcohol is 1o with no beta branching, the reaction proceeds with Sn2.

KNOW THIS REACTION x3

Term
Add X2 to the Double Bond
Definition

Use X2 in CH2Cl2, trans addition.

 

KNOW THIS REACTION

Term
Add XOH to the Double Bond
Definition

Use X2 in water. Trans, Mark

 

KNOW THIS REACTION

Term
Open the Expoxide Ring
Definition

1. Acid-catalyzed ring opening (H2SO4 and the nucleophile, OH attacks such that most stable carbocation is formed)

2. Nucleophilic ring opening (nucleophile and its salt, attack occurs at least sterically hindered carbon)

 

KNOW (2)

Term
Brominate at the Allylic Position
Definition
Use NBS, light, CH2Cl2. Radical mechanism.
Term
Hydrate an Alkyne to a Ketone or Aldehyde
Definition

1. Hydroboration (Same reagents as alkene reaction) forms both ketone and aldehyde based on triple bond position

2. Acid-catalyzed hydration (H2SO4 and HgSO4) forms only ketones

Term
Form an Alkyne from an Alkene
Definition
Double dehydrogenation (X2 and CH2Cl2 THEN NH4(l))
Term
Halogenate an Alkane
Definition

X2, light by radical mechanism

 

KNOW THIS REACTION

Term
Make a Glycol
Definition
Use OsO4 on the double bond. Cis addition of OH forms glycol (diol).
Term
Cleave the Double Bond
Definition
Use O3, forms carbonyl groups at both ends.
Term
Form a Ketone or Carboxylic Acid from an Alcohol
Definition

1. Use H2CrO4, forms Carboxylic acid if starting from 1o, forms Ketones if starting from 2o alcohol

2. Use PCC, forms Ketone if starting from 1o alcohol (stops short)

Term
Add H2 to the Triple Bond
Definition

1. H2 and Pt, Proceeds to completion (yields alkane)

2. H2 and Lindlar catalyst (Usually palladium), forms cis alkene

Term
Form an Epoxide (Ring)
Definition

1. First X2 and H2O, then NaOH and H2O (nucleophilic substitution conserves alkene stereochemistry)

2. Peracetic acid, CH2Cl2 (also conserves alkene stereochemistry)

Term
Convert an Alcohol to an Alkoxide
Definition
React with Active Metal
Term
Form an Ether
Definition

1. Williamson Ether Synthesis (R-OX and alkoxide ion)

2. Acid-catalyzed dehydration synthesis (H2SO4 at 140oC)

3. Acid-catalyzed addition of alcohol to alkene (H2SO4, with 1o alcohol)

Term
Add H2 to the Double Bond
Definition

1. Use H2 and Pt, Cis addition

2. Use H2 and (S)-BINAP RuCl3, Trans addition

Term
Form a Bromoalkane from Alcohol
Definition

Use PBr3

 

KNOW THIS REACTION

Term
Form a Chloroalkane from Alcohol
Definition

Use SOCl2 and Pyridine or Et3N

 

KNOW THIS REACTION

Term
Add HX to the Double Bond
Definition

Use HX, trans addition

 

KNOW THIS REACTION

Term
Form an Aldehyde from Alcohol
Definition
Use PCC; the alcohol must be 1o
Term
Add HX to the Triple Bond
Definition
Use HX, Mark
Term
Dehydrate a Double Bond
Definition

Acid-catalyzed dehydration (H2SO4)

 

KNOW THIS REACTION

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