Test 4, Ch 9,10,11

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 +