Midterm 1

Organic Chemistry 1

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Question 1

Assign the formal charges to the atoms of molecules A and B.

What is the relationship between A and B?

Solution

A and B are Resonance Structures

Question 2

Indicate the number of hydrogen atom(s) on each carbon atom of the following molecule.

Give the hybridization of each carbon atom.

What is the carbon atom with the most acidic hydrogen(s)?

Solution

The most acidic hydrogen is on carbon atom number 8 (hybridization effect)

Question 3

Draw as many resonance structures as you can for the compounds C and D

(Do not draw the sameresonance structure twice).

Circle the weaker base, and briefly justify your answer.

Solution

D has more resonance forms ⇒ D is more stable than C.

D is the weaker base

Question 4

Name compound E and draw a skeletal structure for this compound.

Draw 3,4-dimethylheptane. What is the relationship between this compound and E?

Solution

3,4-dimethylheptane:

Same molecular formula as E

Different connectivity

⇒ Constitutional Isomers

Question 5

Draw the possible isomers having the formula C₃H₈O

Solution

Question 6

Draw all possible products resulting from the substitution of one hydrogen of the compound F by one bromine atom via a radical process.

Solution

4 equivalent hydrogen groups ⇒ 4 products:

Question 7

Follow the flow of electrons indicated by the curved arrows and predict the products of the reaction:

Solution