The City College of New York

C.U.N.Y.
Department of Chemistry
Third Examination
Organic Chemistry I: Chemistry 26100 Spring 2015
Prof. Salame
Name: ID:
1. ______, 2. ______, 3. ______, 4. ______, 5. ______, 6. ______
7. ______, 8. ______ 9.______, Total. _________

1. What is the correct IUPAC name for the following compounds?

a) (4 pts)

OH

b) (4 pts)

2. (4 pts) Predict the major monobromination product in the following reaction.

hv
+ Br2 

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 3. What is the product for the following sequence of reactions?

a) (4 pts)
1. HI

2. t-BuOK, t-BuOH

b) (5 pts)

i) Br2, h
ii) C2H5ONa/C2H5OH, heat
Methylcyclopentane ?
iii) BH3, THF
iv) H2O2, OH

c) (5 pts)

Br2 (CH3)3CO:¯ HBr

  
hv (CH3)3COH ROOR

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 4. (10 pts) Suggest the most appropriate synthetic method for the following reaction:



5. (9 pts) Suggest the most appropriate synthetic method for the following reaction:



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 6.
a) (6 pts) A compound with the molecular formula C10H13Cl gave the following 1H NMR
spectrum:
 1.6 (2H, singlet)
 3.1 (6H, singlet)
 7.2 (5H, multiplet)
The most likely structure for the compound is:

b) (6 pts) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C7H12O4? The 13C-NMR spectrum shows peaks at 14.1, 40.8, 61.0 and 166.8
ppm.
 1.3 (6H, triplet)
 3.3 (2H, singlet)
 4.3 (4H, quartet)

c) (6 pts) An unknown compound A has the molecular formula C12H16O. Compound A absorbs
strongly in the IR at 1700 cm-1. The NMR spectral data for compound A are given below. What
is the structure of compound A?
Absorption ppm Ratio of absorbing H’s
Singlet 1.0 6
Triplet 1.2 3
Quartet 2.2 2
multiplet 7.1 5

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 d) (6 pts) An unknown compound X has the molecular formula C10H11O2Br. Compound X shows
a strong absorption in its IR spectrum at 1700 cm-1. The 1H NMR spectral data for compound X
is given below. What is the structure of compound X?
Absorption ppm Ratio of absorbing H’s
Double 1.0 3
Singlet 5.5 2
Quartet 4.4 1
multiplet 7.2 5

7. (12 pts) Show how you would synthesize the following compound. As starting material, you
may use any alcohols containing five or fewer carbon atoms and any necessary solvents and
reagents.

OH

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 8. (12 pts) Propose a detailed, stepwise mechanism for the following transformation:
(Use curved arrows to show movement of electrons)

OH H3O+


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 9. (12 pts) Propose a detailed, step-by-step mechanism for the reaction pathway shown below.
(Use curved arrows to show movement of electrons)

H2SO4

OH

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