Organic Chemistry: Finding Unsaturation & Oxidation Levels in Problem Set 7, Assignments of Chemistry

This problem set from chem 225b, comprehensive organic chemistry, covers the topics of degree of unsaturation and oxidation levels of organic compounds. Students are required to find the amount of k2cr2o7 needed to oxidize cyclohexanol, identify structures of compounds based on their reactions and heats of formation, and understand the addition of organometallic reagents to aldehydes and ketones. The document also mentions the importance of the alcohol module in orgo for reviewing fundamental reactions.

Typology: Assignments

Pre 2010

Uploaded on 11/08/2009

koofers-user-4lw
koofers-user-4lw 🇺🇸

4.8

(2)

10 documents

1 / 3

Toggle sidebar

This page cannot be seen from the preview

Don't miss anything!

bg1
Chem 225b
Comprehensive Organic Chemistry
Problem Set 7
Chapter 8
Due: Monday, March 27, 2006
We have discussed Degree of
Unsaturation (D.U.) as it relates to
hydrocarbons. How do you find the
D.U. if other atoms are present?
Fear not! There is an html
document and an independent,
different Powerpoint presentation
on this topic. The subject of
oxidation levels of organic
compounds is a useful concept.
Check it out here Oxidation
Levels.The alcohol module in
ORGO will give you a good
review of some of the fundamental
reactions discussed in class and in
Chapters 8 and 9.
1. How many grams of K2Cr2O7
in aqueous H2SO4 are required to
oxidize 20 grams of cyclohexanol
to cyclohexanone? [This is a redox
reaction from Gen. Chem. Derive
the balanced equation and show
your work.]
Victor Grignard (1871-1935)
Co-Nobel Prize in Chemistry (1912)
2. (R)-(-)-Carvone is reduced in the presence of hydrogen to form two
carvomenthones, A and B (C10H18O). A is less stable than B. (Use what
you know about cyclohexane to make this evaluation.) Reduction of A
pf3

Partial preview of the text

Download Organic Chemistry: Finding Unsaturation & Oxidation Levels in Problem Set 7 and more Assignments Chemistry in PDF only on Docsity!

Chem 225b Comprehensive Organic Chemistry Problem Set 7 Chapter 8 Due: Monday, March 27, 2006 We have discussed Degree of Unsaturation (D.U.) as it relates to hydrocarbons. How do you find the D.U. if other atoms are present? Fear not! There is an html document and an independent, different Powerpoint presentation on this topic. The subject of oxidation levels of organic compounds is a useful concept. Check it out here Oxidation Levels.The alcohol module in ORGO will give you a good review of some of the fundamental reactions discussed in class and in Chapters 8 and 9.

  1. How many grams of K 2 Cr 2 O 7 in aqueous H 2 SO 4 are required to oxidize 20 grams of cyclohexanol to cyclohexanone? [This is a redox reaction from Gen. Chem. Derive the balanced equation and show your work.] Victor Grignard (1871-1935) Co-Nobel Prize in Chemistry (1912)
  2. ( R )-(-)-Carvone is reduced in the presence of hydrogen to form two carvomenthones, A and B (C 10 H 18 O). A is less stable than B. (Use what you know about cyclohexane to make this evaluation.) Reduction of A

with NaBH 4 provides C and D while B gives E and F. Compounds C-F are converted to their respective tosylates G-J and their rates of elimination and products formed upon exposure to EtONa/EtOH were studied. Rates of elimination: G > H and I > J. Tosylate G forms only K , H forms M and I forms M (major) and L (minor). What are the structures A-J? Explain all transformations involved.

  1. Two bottles on a shelf have had their labels fall on the desktop. Both of the labels read "C 5 H 11 Br". A student decides to run some reactions on the contents bottle A and B to determine the structures of the two compounds. She also has access, as do you, to heats of formation. From the flow chart below, determine the structure of A and B and identify C- I. Show your reasoning.
  2. For EtOH (pKa = 15.9) + NaOH in equilibrium with EtONa + H 2 O (pKa = 15.7), a) What is the value of Keq? Show work. b) How much of each base is present?