CHEM 2114 Organic Chemistry I Unit 5 Practice Problems

 

1.       Name the following compounds:

a)                                                                        b)

c)                                                                        d)

 

      e)                                                                        f)

 

2.      Draw the following compounds:

a.   trans-6-bromo-3,4-dimethyl-3-decene

b.   3,3-dimethyl-1,4-cyclohexadiene

c.   (E)-3-bromopent-2-ene

d.   (Z)-3-ethyl-2-phenyl-2-hexene

 

3.      Calculate the number of elements of unsaturation for the formula, C6H11NO.  Draw four reasonable structures for this formula, including one with a nitrile and one with a secondary amide.

 

4.      Calculate the number of elements of unsaturation for C7H6O2.  Draw one reasonable structure.  What functional group(s) is/are present in your structure?

 

 

5.      Which of the following alkenes in each pair is higher energy?

 

a.   cis-cyclohexene vs. trans-cyclohexene

b.   cis-2-pentene vs. trans-2-pentene

c.   3-methylbut-1-ene vs. 2-methylbut-2-ene

d.   3-methylcyclopentene vs. 3-methylcyclobutene

 

6.      Predict the major elimination product from the following reactions.

a.

 

b.

 

c.

 

d.

 

e.

 

f.

 

g.

 

h.

i

 

j.

 

k.

 

 

7.      Draw the mechanism for the reactions shown in

a.       question 6a

b.      question 6e

c.       question 6g

d.      question 6i

e.       question 6k

 

8.      Draw the structure of the major product formed when each of the following reagents reacts (individually) with 1-deutero-2-methylcyclohexene:

                                                                                            

a.       HBr

b.      HBr/t-BuOOtBu/heat

c.       Br2/CH2Cl2

d.      Dilute aqueous acid

e.       (1)  Hg(OAc)2 (aq)

(2)  NaBH4

f.   (1)  BH3

      (2)  H2O2/NaOH (aq)

g.   (1)   Hg(OAc)2/CH3OH

      (2)  NaBH4

h.   Br2/H2O

i.    H2/Pd

j.    OsO4/H2O2

k.   dilute KMnO4

l.    MCPBA/CH2Cl2

m.   CH3CO3H/H2O

n.   (1)  O3

      (2)  (CH3)2S

o.   CHBr3/NaOH/H2O

 

9.      Draw the mechanism for the reaction shown in

a.       question 8a

b.      question 8c

c.       question 8d

d.      question 8e

e.       question 8g

f.       question 8h

 

10.   Draw the intermediate and final products formed in the following multistep reactions.

a.

 

b.

 

c.

 

 

11.    Complete the following syntheses by showing the appropriate intermediate product (NOT a reactive intermediate) and the best reagents.

a.

 

b.

 

c.

 

d.

 

 

12.   Propose a mechanism for each of the following reactions.

a.

 

b.

 

 

13.   Name the following compounds:

a.                                                                     b.

 

c.                                                                     d.

 

14.   Draw the following compounds:

a.       2,5-dibromo-2,5-dimethyl-3-hexyne

b.      trans-6-ethyloct-2-en-4-yne

c.       1,6-dibromo-2,4-hexadiyne

 

15.   Identify the products formed in the following acid/base reactions:

 

 

16.   Predict the product formed in the following reactions:

 

17.   What reagents are needed to perform the following reactions?

a.

 

b.

 

18.   Predict the major product formed in the following reactions:

 

 

 

 

 

 

 

19.   Complete each of the following reactions by drawing the structure of the intermediate product(s) and the best reagents.

 

 

 

 

 

 

20.  Draw the mechanism for each of the following reactions.

 

 

 

21.   Show how you would complete the following syntheses.

 

 

 

 

22.  A compound with the formula C5H12O gave the following IR spectrum.  Draw at least one structure that is consistent with the formula and IR.

 

 

 

 

 

 

 

23.  A compound with the formula C6H12O gave the following IR spectrum.  Draw at least one structure that is consistent with the formula and IR.

 

 

 

24.  A student attempted the following reaction.  The resulting product gave the following IR spectrum.  Did the student obtain the desired product?  Explain and support your answer using the data from the IR spectrum.