Test 4, Ch 9,10,11

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CHM 2210 – Fall 2012 – Test 4 Name (print):_________________________ 1. What is the IUPAC name for the following compound?

a) b) c) d)

3-methyl-1-penten-4-yne 3-methyl-1-buten-4-yne 4-methyl-4-penten-1-yne 4-methyl-4-buten-1-yne

2.

What is the major organic product obtained from the following reaction? 2 equiv Br2

a) b) c) d)

2,3-dibromobutane 2,2,3,3-tetrabromobutane 2,3-dibromobutene 2,2-dibromobutane

3.

What is the best choice of reagent(s) to perform the following transformation? ?

a) b) c) d)

H2/Pd H2/Lindlar catalyst Na/NH3 BH3; then H2O2, NaOH

1

4. Which of the labelled hydrogen atoms in the following molecule is the most acidic (i.e. most reactive with NaNH2)? 3 2 H H H H H H 1 H H H H 4

a) b) c) d)

1 2 3 4

5.

The structure of the product of the following sequence of reactions would be 1 - NaNH2 2 - CH3CH2Br 3 - H2, Lindlar's Catalyst I II III IV Br

a) b) c) d)

I II III IV

2

6.

What is the major organic product obtained from the following reaction? O H 1 - BH3 2 - H2O2, NaOH O H OH

I a) b) c) d) I II III IV

II

III

IV

7.

What is the major organic product obtained from the following reaction? O H H2O, H2SO4 HgSO4 O H OH

I a) b) c) d) I II III IV

II

III

IV

8.

What is the major organic product obtained from the following reaction? Li NH3 Na I II III IV NH2

a) b) c) d)

I II III IV

3

9.

In the following elimination reaction, the product(s) of the reaction is(are) CH3O- Na+ 2-bromohexane CH3OH

a) b) c) d) e)

CH3CH2CH2CHCHCH3 CH3CH2CH2CH2CHCH2 An equimolar mixture of a and b. A mixture of the major product a with the minor product b. A mixture of the major product b with the minor product a.

10. Consider the SN2 reaction of butyl bromide with OH- ion. Assuming no other changes, what effect on the rate would result from simultaneously doubling the concentrations of both butyl bromide and OH- ion? CH3CH2CH2CH2Br + OH-  CH3CH2CH2CH2OH + Bra) b) c) d) e) No effect. It would double the rate. It would triple the rate. It would increase the rate four times. It would increase the rate six times.

11. Which of the following is most reactive as a nucleophile?

CH3OI a) b) c) d) I II III IV

O H3C C O II
-

H2O III

H2S IV

4

12. What is the major organic product obtained from the following reaction?

Br

NaOCH3 CH3OH I O Br II

O

O

III

IV

a) b) c) d)

I II III IV

13. Which of the following energy diagrams represents the course of an exothermic SN2 reaction? 1
energy

2
energy

3
energy

4
energy

reaction coordinate

reaction coordinate

reaction coordinate

reaction coordinate

a) b) c) d)

1 2 3 4

14. Which is not a polar aprotic solvent?
O
O C H3C CH3
H3 C C N

O S H3C CH3

C H N

CH3

CH3 CH H3C OH

CH3

I a) b) c) d) e) I II III IV V

II

III

IV

V

5

15. Which SN2 reaction will occur most rapidly in aqueous acetone solution. Assume the concentrations and the temperature are the same in each case. a) b) c) d) HO- + CH3CH2-Cl  CH3CH2OH + ClHO- + (CH3)2CH-Cl  (CH3)2CHOH + ClHO- + (CH3)3C-Cl  (CH3)3COH + ClHO- + (CH3)3CCH2-Cl  (CH3)3CCH2OH + Cl-

16. Which of the following gas-phase reactions is a possible chain-terminating step in the light-initiated chlorination of methane? a) b) c) d) Cl–Cl  2 Cl· Cl· + CH4  CH3· + H–Cl CH3· + CH3·  CH3–CH3 CH3· + Cl–Cl  CH3Cl + Cl·

17. Rank the following radicals in order of decreasing stability (most stable > least stable).

CH3

I a) b) c) d) e) I > IV > II > III I > II > IV > III IV > III > II > I III > I > II > IV III > II > IV > I

II

III

IV

6

O N Br

18. Give the product of the following reaction. NBS =

O

Br NBS hv Br I a) b) c) d) I II III IV Br II III IV Br Br Br

19. What is the IUPAC name of the following compound?
Cl

a) b) c) d)

(E)-1-chloro-1,2,3-trimethyl-1-butene (Z)-1-chloro-1,2,3-trimethyl-1-butene...
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