2. What is the product for the reaction below?

+ HBr ?
(A)
 Br
(B)

Br
(C)
CH3

Br
(D)

CH3

Br
(E) none of these

3. What is the product of the following reaction? CH3 O AlCl3 + H3C Cl ((A) ((D) CH3 CH3 Cl O CH3 ((B) ((E) CH3 CH3 CH3 CH3 O CH3 ((C)  CH3 CH3

4. When (S)-3-bromo-1-butene is treated with HBr, two stereoisomeric products form. What is the relationship of these two products? ((A) enantiomers ((B) diastereomers ((C) meso compounds ((D) racemic mixture ((E) cis/trans

5. The major product of the reaction below is: Br H CH3S Na H3C CH2CH3 ((A) ((D) H3CS H H H H3C CH2CH3 H3C CH2CH3 ((B) ((E) H SCH3 Br SCH3 H3C CH2CH3 H3C CH2CH3 ((C) H CH2CH3 H3C CH2CH3

6. What is the final product of the following sequence of reactions? 1) Mg, Et2O 2) O Br ? 3) H3O+ ((A) ((D)  OCH3 ((B) ((E) CH2OCH3 OH ((C) CH2CH2CH2OH

7. Which hydrogens in the following compound will be exchanged most rapidly for deuterium upon reaction with D2O and NaOD? H4 H3 H2 H1 O H5 ((A) H1 ((B) H2 ((C) H3 ((D) H4 ((E) H5

8. The following compound will have a proton NMR spectrum that shows: O CH3 O O CH3 CH3 ((A) two singlets, area ratio 3:1. ((B) two singlets, area ratio 9:1. ((C) three singlets, area ratio 3:3:6. ((D) four singlets, area ratio 3:2:6:1. ((E) six singlets, area ratio 3:3:3:1:1:1.

9. The product of the reaction sequence H2O2 CH3 BH3 NaOH ? ((A) CH3 OH ((B) CH3 OH ((C) CH3 BH2 ((D) CH3 OH ((E) none of the above

10. When methylamine (CH3NH2) reacts with methyl bromide (CH3Br) to give dimethylamine, the methylamine: ((A) acts as an electrophile ((B) acts as a Lewis acid ((C) acts as a Bronsted-Lowry acid ((D) acts as a Bronsted-Lowry base ((E) acts as a nucleophile in an SN2 reaction

11. Please rank the acidity of the following four compounds, from most acidic to less acidic. (5 points) OH O O CH3CH2OH F3C OH H3C OH CH3CH2CH3 A B C D E

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