91Ó°ÊÓ

Question: Draw the eight constitutional isomers having the molecular formula C₅H₁₁Cl .

1. Give the IUPAC name for each compound (ignoring R and S designations).
2. Classify each alkyl halide as $1°,2°or3°$.
3. Label any stereogenic centers.
4. For each constitutional isomer that contains a stereogenic center, draw all possible stereoisomers, and label each stereogenic center as R or S.

Question: Which compound in each pair has the higher boiling point?

a.

b.

Question: Draw the products of each nucleophilic substitution reaction.

b.

c.

d.

e.

f.

Question: Which of the following molecules contain a good leaving group?

a.

b.

c.

d.

Question: Rank the species in each group in order of increasing leaving group ability.

a. Br^-,Cl^-,I^-

b. NH₃,H₂S,H₂O

Question: Which of the following nucleophilic substitution reactions will take place?

a.

b.

Question: Chondrocole A is a marine natural product isolated from red seaweed that grows in regions of heavy surf in the Pacific Ocean. (a) Predict the solubility of chondrocole A in water and . (b) Locate the stereogenic centers and label each as R or S. (c) Draw a stereoisomer and a constitutional isomer of chondrocole A.

Question: Rank the species in each group in order of increasing nucleophilicity.

a.CH₃CH₂S^- ,CH₃CH₂O^-,CH₃CO₂^- in CH₃OH

b. CH₃NH₂ ,CH₃SH,CH₃OH in acetone

c. ^-OH ,F^- ,Cl^- in acetone

d. HS^- ,F^- ,I^-in CH₃OH

Question: Classify each solvent as protic or aprotic.

1. (CH₃)₂CHOH
2. CH₃NO₂
3. CH₂Cl₂
4. NH₃
5. N(CH₃)₃
6. HCONH₂

Question: Why is the amine N atom more nucleophilic than the amide N atom CH₃CONHCH₂CH₂CH₂NHCH₃?