Organic Chem - Oxidation and Reductions

  • Thread starter gabe1scott
  • Start date
  • #1

Homework Statement



Im having some problems with some oxidation and reduction mechanisms. Im not sure if I am doing them correctly.

Homework Equations



1. O=C=O + CH3-MG++I-

2. Acetone + NH4+, Na+ H3BCN

The Attempt at a Solution



1. I break one of the bonds from the oxygen and protonate it to give me a carboxylic acid. Im not sure if I dehydrate it to form 2-propanol.

2. I don't really know where to start with this one. I think the NH4 adds a hydrogen to the oxygen, and then the carbon nitrile attacks and forces off the OH to form water, leaving Propane substituted with a CN group.
 

Answers and Replies

  • #2
TeethWhitener
Science Advisor
Gold Member
1,798
1,148
1. O=C=O + CH3-MG++I-

2. Acetone + NH4+, Na+ H3BCN
1. The first one is a Grignard reaction. I've never thought of it specifically as a redox reaction, but I guess it is. Anyway, the methyl anion is highly nucleophilic and attacks the electrophilic carbon on CO2 to give acetate. Upon acidic workup, the organic product is acetic acid.

2. The second one requires you to know that sodium cyanoborohydride is a weak reducing agent (weaker than sodium borohydride). The combination of acetone and ammonium will give an iminium ion (the carbonyl C=O is replaced with a C=NH2+). The cyanoborohydride reduces this to an amine. So the final product is isopropylamine (2-aminopropane in IUPAC language).
 
  • Like
Likes jim mcnamara

Related Threads on Organic Chem - Oxidation and Reductions

Replies
2
Views
5K
  • Last Post
Replies
0
Views
960
Replies
3
Views
6K
  • Last Post
Replies
7
Views
5K
  • Last Post
Replies
3
Views
1K
  • Last Post
Replies
2
Views
2K
Replies
2
Views
23K
  • Last Post
Replies
10
Views
20K
Replies
1
Views
9K
  • Last Post
Replies
1
Views
6K
Top