Organic Chemistry

1. For each pair of reagents below, perform the following: A) Identify the most acidic proton. B) Draw the products of the acid-base reaction. C) Draw the curved arrow mechanism for the forward reaction only. D) Label the acid, base, conjugate acid, and conjugate base. E) Determine which side of the reaction is favored and draw the appropriate equilibrium arrow.

Write mechanisms that account for the products of the following reactions. Describe a category of the reactions (e.g. E1, E2, S1, and S,2) Is rearrangement possible?

3. Relationship between the given molecules • D-glucose and L-glucose - Both are enantiomers of each other. • D-glucose and D-galactose-Both are diastereomers of each other. And also, the difference between these two is found in C4 carbon so these two are epimers of each other. • L-glucose and L-fructose- Both are constitutional isomers of each other.

Discuss whether the results from Series I concur with the interfacial film theory of Schulman and Cockbain.

Q1. (a) Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH₂)₂C=CH₂ Name of mechanism Mechanism (b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with ethanolic potassium hydroxide. (1) Explain what is meant by the term stereoisomers. (1) Draw the structures and give the names of the two stereoisomers of but-2-ene. Stereoisomer 1 Name (iii) Name this type of stereoisomerism. Page 1 of 13 Stereoisomer 2 (c) When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide, 2-methylpropan-2-ol is formed as shown by the following equation. CH3 H₂C-C-CH3 + KOH → Br Name CH3 H3C-C-CH3 + KBr OH State the role of the hydroxide ions in this reaction. (d) Write an equation for the reaction that occurs when CH₂CH₂CH₂CH₂Br reacts with an excess of ammonia. Name the organic product of this reaction. Equation Name of product (6) (5) (1)

Around 10% excess of Chloroacetyl chloride (1.1 equivalents1.1 mmol) was used; calculate the number mmols to exact mass(mg) and then convert to pL given the MW and density (MW 113mg/mmol; d = 1.417 mg/µL).

Question 53 (0.0001 points) (4 marks) Consider the unbalanced reaction below, which occurs in an acidic aqueous solution. MnO4 + Fe²+® Fe³+ + Mn²+ a. Identify the half-reactions (oxidation, reduction) (1 marks) b. Balance the reduction equation (1 marks) c. Balance the oxidation equation (1 marks) d. Balance the overall equation (1 marks)

Q2: Predict what the main product of the following organic reactions?

Draw a reasonable curved-arrow mechanism for the reaction below converting the starting material to the product indicated. Be sure to explicitly draw all the lone pairs present on heteroatoms (e.g. O, N, S, Cl etc). Draw out all relevant resonance structures. Check for conservation of charge and conservation of mass. Honor Grossman's Rule.

(4 pts.) 2. Give the starting materials used in each retro-synthesis. COOH the- Fo