QUESTION 1

1. Any reaction involving a carbonyl group and a strong acid begins with the same first step, which is __________________ of the carbonyl oxygen.

QUESTION 2

1. Using condensed molecular formulas (C_#H_#X_#Y_#) for your answers, predict the products of the reactions of C₆H₅CH₂CHO (phenylacetaldehyde) with these reagents, and identify the functional group produced in the product. Note that the T_x symbol above allows you to do a subscript.

   a. NaBH₄ / CH₃OH

   b. 1. CH₃MgBr; 2. H₂O

   c. Ph₃P=CHCH₃

   d. CH₃CH₂OH (excess), H+

   e. (CH₃)₂CHNH₂, H+

QUESTION 3

1. Draw the structure of the compound whose molecular formula is C₉H₁₀O and has the following proton NMR data:

   triplet at 1.2 ppm, integrates to 3H

   quartet at 2.7 ppm, integrates to 2H

   doublet at 7.3 ppm, integrates to 2H

   doublet at 7.7 ppm, integrates to 2H

   singlet at 9.9 ppm, integrates to 1H

QUESTION 4

1. What are the reagents needed for each of the following transformations?

QUESTION 5

1. Draw the starting materials needed to form (CH₃)₂C=CHCH₂CH₃ using a Wittig reaction.

QUESTION 6

1. Provide the products that result when (CH₃)₂NCH=C(CH₃)₂ undergoes hydrolysis in dilute acid.

   Path: p Words:0

QUESTION 7

1. Draw the structures of the five intermediates and products that form in the acid-catalyzed mechanism in the following reaction.

   (Above should be “Products“ instead of singular)

QUESTION 8

1. The hydroxyaldehyde shown cyclizes to form a hemiacetal under acidic or basic conditions. Use wedge-dot structures to draw the two stereoisomers formed from the aldehyde when it cyclizes. Explain if the relationship between the products. Is the product mixtureexpected to be optically active or optically inactive?