CHEM212 Summer 2016 Practice Problems 2.

(1) Calculate the oxidation numbers for the carbon atoms in the following compounds:
(a) CH4 ________ (b) CO2 (oxygen counts as -2) _________ (c) CH 3Br _________ (d) CH2Br2
_________

Show that the reaction sequence CH4 CH3Br CH2Br2 involves two 2-electon steps.

Is the reaction CH4 CO2 an oxidation, a reduction or a non-redox reaction? Would you expect it
to be endothermic or exothermic? Why?

(2) Calculate the oxidation levels for each of the compounds (for Tuesdays quiz, be prepared to
show the calculations). The formula is (#C-O bonds + #C-N bonds + #C-Halogen bonds) - #C-H
bonds).

(a) _______ (b) ________ (c) ________ (d) CH3CH2OH ________

(e) CH3CH=O ________ (f) CH3COOH ________ (g) HOCH2CH2OH ________
(h) BrCH2CH2Br ________
(2) Based on the changes in oxidation levels, determine if each of the following reactions is an
oxidation, a reduction, or a non-redox reaction.

(a) ______________________________

(b) ______________________________

(c) The sequence:

______________________________

(d) ______________________________

(e) ______________________________
(f) In (c), what types of reaction are the first and second steps? What reagent(s) would be used
for each?

1st Type: ______________________________ Reagent: _______________________________

2nd Type: ______________________________ Reagent: _______________________________

(3) Predict the products from the following reactions or reaction sequences. Be careful to
consider stereochemistry!
(a)

(b)

(c)

(d)
(3) (supplemental) Worth thinking about for students aiming to really understand.
First a little stereochemistry review what is the stereochemical relationship between the
products from reaction sequences (b) and (c)? Enantiomers, diastereomers or identical?
What would happen if instead of H 2/Lindlaars, I had chosen to pose questions (e) and (f) where
the reducing agent for the first step was Na/NH 3(l) instead? What would be the relationships
between the products b, c, e, and f?
(4) Devise synthetic routes that would allow you to prepare each of the following target
molecules starting from acetylene (ethyne, C 2H2). You may use any other reagents you think are
appropriate. Show both a retrosynthetic analysis and a synthetic scheme. Remember, you are
working backwards from the TM, ultimately needing to start with acetylene itself, so ALL of the
syntheses are going to begin with either one or two alkyne alkylation reactions. Alkylations of
alkenes and alkanes DO NOT WORK in this manner, so if you need to create C-C bonds to get to
the TM, those steps MUST be done before any FGIs on the alkyne.

(a)

(b)
(c)

(d)

(e)

(f)

(g)
(h)

Try to think of some additional target molecules that could be made using the combinations of
the alkylation and C-C bond-forming reactions and FGIs discussed so far. Even though you can
only use methyl and primary R-X compounds in the alkylation reactions, you still have a very
large number of possibilities.