CM1121: Organic Chemistry 1

Tutorial 1 (Chapters 2, 4 and 5) Q1. Study the structure of brevetoxin. Make a list of the different types of functional groups and the number of rings of different sizes.

Q2.

Draw and name a structure corresponding to each of these descriptions: (a) An aromatic compound containing one benzene ring with the following substituents: two chlorine atoms having a para relationship, a nitro group having an ortho relationship to one of the chlorine atoms, and an acetyl group having a meta relationship to the nitro group. (b) An alkyne having a trifluoromethyl substituent at one end and a chain of three carbon atoms at the other with a hydroxyl group on the first atom, an amino group on the second, and the third being a carboxyl group.

Q3.

What kind of hybridization do you expect for each carbon atom in the following molecules?

Q4.

Suggest detailed structures for these molecules and predict their shapes: (a) CH2=NCH3 , (b) (CH2)2O

LAM (2014)

CM1121: Organic Chemistry 1

Q5.

Allene, H2C=C=CH2, is somewhat unusual in that it has two adjacent double bonds. Draw a picture showing the orbitals involved in the and bonds of allene. Is the central carbon atom sp2- or sp- hybridized? What about the hybridization of the terminal carbons? What shape do you predict for allene?

Q6.

Each of these electrophiles could react with a nucleophile at two different atoms. Identify these atoms and draw a mechanism for each reaction together with the products from each. (a) (b)

Q7.

Predict the product(s) of each of the following reactions by interpreting the flow of electrons as indicated by the curved arrows: (a)

(b)

LAM (2014)