Organic Chemistry Worksheet

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Science

Cuyamaca College

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Solve this worksheet for an organic chemistry class.

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Midterm 2, 8/3/2020 Name: Question 1 (5 points): Multiple Choice. When CH3Li is added to an ester, the product after workup is: a.) A carboxylic acid b.) An aldehyde c.) A ketone d.) An alcohol e.) An amine When a single equivalent of a cuprate agent is added to an acyl chloride, the product after workup is: a.) A carboxylic acid b.) An aldehyde c.) A ketone d.) An alcohol e.) An amine In a conjugated system, how many consecutive sp2-hybridized carbons are required to make a set of 8 π-type molecular orbitals? a.) 2 b.) 4 c.) 6 d.) 8 e.) none of the above Which of the following carboxylic acid derivatives is least reactive towards nucleophilic addition? a.) an acid chloride b.) an acid anhydride c.) an ester d.) an amide e.) a carboxylate ion N In “pyrazine” a.) s b.) p c.) sp d.) sp2 e.) sp3 N , the nitrogen lone pairs are placed in which kind of atomic orbital? Question 2 (21 points): Short Answer ● “Anthracene” has the following structure: a.) Is this molecule expected to be aromatic or anti-aromatic? b.) Would you expect phenanthrene to absorb at longer or shorter wavelengths of light compared to tetracene: O ● In class, we examined the resonance structures of furan: O O + N O Nitrofurans such as are core structures in many antibiotics, and can be prepared from furan by electrophilic aromatic substitution. Would you expect this process to be faster or slower than the nitration of benzene? ● Predict the kinetic and thermodynamic aldol condensation products produced from the following: O 1.) LDA, slight excess, cold 2.) CH2O 3.) H3O+ workup, heat O 1.) NaOH, >2x ketone, warm 2.) CH2O 3.) H3O+ workup, heat ● In your own words, explain why heat favors condensation products over addition products. ● Which of the following structures is most acidic? HO OH OH Cl Cl Cl Question 3 (24 points): Chemistry of polyenes. Predict the kinetic and thermodynamic products formed when the following diene reacts with deuterated hydrobromic acid, “DBr.” Be sure to show where the deuterium atom resides in your products. DBr (conc.) Question 4 (6 points): Nomenclature. Provide systematic names for the following compounds. Br Br Question 5 (19 points): Aromatic and anti-aromatic compounds. The following is a representation of the planar trimethylcyclopropenium cation: + C a.) Draw a set of three resonance structures to describe this ion. b.) Is this compound aromatic or anti-aromatic? c.) Sketch a Frost circle for this compound, and calculate a bond order for the π-system in the ring. d.) The trimethylcyclopropenide anion is analogous to the cation above, but with two extra electrons in the ring by a negatively charged carbon. Is this structure aromatic, or anti-aromatic? What is the expected bond order of the πsystem? Question 6 (12 points): Mechanisms, part 1. Given the following transformation: O Cl H N (large excess) O N Reminder: Amines are somewhat basic, like NH3. a.) Provide a mechanism for the reaction using proper arrow formalism. b.) Draw an additional resonance structure of the product that shows separated formal charges. Question 7 (18 points): Mechanisms, part 2. Given the following transformation: H3O+ a.) What electrophile must be formed in the first step? (Hint: The hydronium ion reacts with a double bond in the first step of this reaction, which is closely related to nitration chemistry.) b.) Based on your answer to (a), use proper arrow formalism to diagram this reaction mechanism. Question 8 (23 points): Mechanisms, part 3. Diagram the following transformation using proper arrow formalism: O 1.) NaOH, then H+ workup 2.) H3O+, heat O Question 9 (12 points): Guided synthesis. Predict the major end product that results from the following reaction sequences. O 1.) NaOH, excess ketone 2.) H3O+, heat 3.) CH3Li, CuI 4.) NaBH4, workup a.) 1.) NaOH (excess), H2O O O 2.) SOCl2 3.) - O b.) 1.) O - O , then H+ workup 2.) NaOH (1 eq.), then CH3Br O 3.) H3O+ (excess), heat c.) Question 10 (12 points): Retrosynthesis. Specify the carbonyl nucleophile and carbonyl electrophile required to form the following molecules using Aldol or Claisen-type chemistry: O Nucleophile: O Electrophile: O O Nucleophile: Electrophile:
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