Name:

Student #:
Chem 2OD3/ChemBio 2OB3
(Circle the appropriate course code)
Assignment #4
Instructor: Dr. R. Wylie

Due: March 20th, 2015

1) SYNTHESIS (30 points)

(A) Suggest a stepwise synthesis for 5-methylhexanal from 3-methyl-1-bromobutane.

(B) Provide a stepwise synthesis for the following.

(C) Provide a stepwise synthesis for the following.

(D) Propose a stepwise synthesis for the following conversion.

O
Br

(E) Using ethyl 3-methylbutanoate as your only source of carbon and using any other reagents
necessary, propose a stepwise synthesis for the following conversion.
O

(F) Propose a stepwise synthesis for N-propylbutanamide, using 1-propanol and/or

carbon dioxide as your only source of carbon and using any other reagents necessary.

2) Fill in the blanks for the following pathways (16 points)

3) Fill in the blanks and explain the factors that might account for the formation of the products
in each reaction. (14 points)

4) Provide the structures for the major product(s) formed under the following conditions. Include
appropriate stereochemistry. Show all appropriate transition states that rationalize the formation
of each product. (15 points)

5) Provide a detailed reaction mechanism (arrow pushing) for the following reaction. You must
show all proton transfers for full marks. (15 points)

SPECTROSCOPY (10 points)

For the following 2 questions calculate the hydrogen defiency index from the molecular formula
and determine the structure using the NMR and/or IR data. Clearly identify the NMR and IR
peaks with their appropriate Hs or functional groups.
(1) A compound with molecular formula C9H10O2 exhibits a triplet at 1.2 (I=3), a quartet at
2.6 (I=2), a doublet at 7.3 (I=2), a doublet at 8.0 (I=2) and a singlet at 11 (I=1) in
its 1HNMR spectrum. What is the structure for this compound?

(2) A compound with molecular formula C8H14O3 exhibits a triplet at 1.0 (I=6), a sextet at
1.6 (I=4) and a triplet at 2.2 (I=4) in its 1HNMR spectrum. Its IR spectrum shows
two strong absorption bands near 1850 & 1750 cm-1. What is the structure for this
compound?