Chemistry

Chemistry 3B

Midterm 2 Review Worksheet

Q1. Draw a structure for the following compounds. Use flat rings for cycloalkanes, and bond-line notation for all others

1. trans-4-oxo-octenal
2. 2,2-dimethyl-1,4-cyclohexadione
3. hemi-ketal derived from the reaction of 2-butanol with cyclohexanone
4. the imine derived from the reaction of p-chloroaniline with m-bromobenzaldehyde
5. aldol product of butan-2-one and benzaldehyde
6. acetal derivative from the reaction of acetaldehyde with ethanol
7. LDA
8. Formaldehyde
9. Acetophenone

Q2. Predict the following compounds and predict the class of compounds (hydrazone, oxime, imine)

1. Propan-2-one + ethanamine
2. Propan-2-one + hydroxylamine (NH2OH)
3. Propan-2-one +  hydrazine (H2NNH2)

Q3. Answer the following questions based on the following structures of the three sugars in their pyranose forms shown below:

[pic 1]

1. Draw the structure of alpha-D-2, 6-dideoxy-2,6-diaminomannose using a chair conformation similar to the one shown for mannose.

1. Draw the Haworth projection of beta-D-glucopyranose

Q4. Predict the organic products and reactants:

[pic 2]

Q5. Predict the organic product of the following reactions:[pic 3]

Q6. Write arrow-pushing mechanisms of the following:

a)[pic 4]

b)

[pic 5]
c)

[pic 6]

d)

[pic 7]

e)

[pic 8]

Q 7.

[pic 9]

Both the peer reviewers felt that the questions looked pretty good. Therefore, I just decided to add a few more questions to my review worksheet. Other than that, I found some really good questions in the old midterms. I include them as well, since it will give students more practice of real midterm questions.

Silica- polar?

TLC question

SN1 SN2 rxn

Elimination product?? Alkenes

SN1 preference – tertiary > sec> primary