Assignment 1

Student ID_________________________ Name________________________

1. Identify suitable reagents for a-h and provide mechanisms for each step.

2. Fill in the missing reagents below and provide mechanisms for each reaction.
3. How to differentiate between alkanes, alkenes and alkynes on the basis of IR spectrum?

4. How to differentiate between (a) Carboxylic acids and amides (b) Aldehydes and ketones on the basis of
IR spectrum?

5. Explain why primary amines show two signals at 3200−3500 cm-1 whereas secondary amines only show
one.

6. Although 2,2-dimethylhexane has a molecular weight of 114, no peak is observed at m/z = 114. The base
peak in the mass spectrum occurs at M−57
(a) Draw the fragmentation responsible for formation of the M−57 ion.
(b) Explain why this cation is the most abundant ion to pass through the spectrometer.
(c) Explain why no molecular ions survive long enough to be detected.
(d) Can you offer an explanation as to why the M−15 peak is not the base peak?

7. Below is the mass spectrum of ethyl butyrate. Explain how the fragmentation at m/z = 88 is formed.

8. Explain the vast difference in pKa values for the following two apparently similar compounds.
9. Provide a mechanism for Birch reduction.

10. Identify reagents that can be used to accomplish each of the following transformations and provide
mechanisms. (For second row compounds only write the reagents 第二排只需寫試劑即可)

11. Draw the mechanism for this reaction. Explain why a nitro group on the ortho position is needed for the
substitution reaction to happen.