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Binghamton University Exam I CHEM 231 F 2014          1)Select the correct name of the following compound

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Binghamton University

Exam I CHEM 231 F 2014         

1)Select the correct name of the following compound.

a	(1-methylhexyl)cyclopentane	d	1-cyclopentyl-2-heptane
b	(1-pentylethyl)cyclopentane	e	2-cyclopentyl-2-heptane
c	2-cyclopentylheptane

2. Which is the best name for the following compound?

          

a	(Z)-2,3,6-trimethyl-2-heptene	d	(E)-2,3,6-trimethyl-2-heptene
b	(Z)-2,3,6-trimethyl-3-heptene	e	(E)-2,4,6-trimethyl-3-heptene
c	(E)-2,3,6-trimethyl-3-heptene

3. What is the correct IUPAC name of the following compound?

                                     

a	cis-1-ethyl-2-methylcyclohexane	c	cis-1-ethyl-6-methylcyclohexane
b	trans-1-ethyl-2-methylcyclohexane	d	trans-1-ethyl-6-methylcyclohexane

4. Which of the following alcohols undergoes dehydration with sulfuric acid most readily? 

 

Arrange the following isomeric alkanes in order of increasing boiling point.                I. n-heptane                II. 2,3-dimethylpentane             III. 2,2,3-trimethylbutane

 

6. Which choice lists the hybridizations of atoms 1, 2 and 3 in the correct order?

         

a	atom 1 is sp, atom 2 is sp2 and atom 3 is sp3	d	atom 1 is sp , atom 2 is sp3 and atom 3 is sp3
b	atom 1 is sp3, atom 2 is sp  and atom 3 is sp2	e	None of the choices a-d are correct
c	atom 1 is sp2, atom 2 is sp2 and atom 3 is sp2

7. Which is the most stable of the following resonance structures?

                       

 

 

 

In the E2 dehydrohalogenation of 2-bromobutane, which conformation(s) below leads directly to the formation of cis-2-butene?

9. Which of the electron-movement arrows below violates the rules of arrow pushing?
10. Which choice lists the shapes of the following carbon containing molecules in the correct order from left to right?

                          

a	Trigonal planar, bent, linear	d	Bent, linear, trigonal planar
b	Bent, linear , trigonal pyramidal	e	Linear, tetrahedral, bent
c	Trigonal pyramidal, linear bent

11. Examine the following of compounds and rank as directed. (32) 4 for all 3 correct otherwise 1 each.
12. For each molecule given if it has a net dipole moment write ‘D’ in the box below, if it does not have a net dipole moment write ‘X’ in the box below. (10)

 

 

13. Name the following compounds using IUPAC rules. (15)

 

14. Determine the formal charge of the bolded atom in each example. (8)

 

15. The electron pair movement depicted in Q produces a second resonance form for the species.

1. Draw the second resonance form (4)

 

c. Which resonance form is more stable, Q or the resonance form you drew? (3)  
 
 

16. The given cation has 2 additional resonance forms.  Draw the 2 other resonance structures and show valid arrow pushing to illustrate the electron movement; then draw the resonance hybrid in the box marked hybrid. (16)

 

17. Draw 5 constitutional isomers with the formula C₄H₈ClBr (You are not required to show the Hs.)  (15)

3 points per correct, non-repeated isomers

 

18.  Circle the side of the acid base equation to which equilibrium lies.  Indicate the key factor that makes a difference in the stabilization in the box to the right of the example. (10)

 

19. Consider the following organic reaction:

 

20. Starting with the given compounds show the step-wise mechanism for dehydration of alcohol.  Circle the 2 key intermediates formed during the progress of reaction. (22)

 

 

 

 

21. The following alkyl halide can eliminate to form 2 different products. A.  Show the 2 products in the 2 boxes below. B. one of the products is the most stable product; write ‘most stable’ in the box under the appropriate drawing and using a key short phrase support your choice. One of the 2 products is made faster than the other.  Select the product and write ‘formed faster’ use a key short phrase to support your choice. Follow directions for box marked C. (20)