QuestionQuestion

Transcribed TextTranscribed Text

Problem 1. Circle the answer to each question a. Which C-X bond has the lowest energy LUMO? b. Which substrate will undergo a solvolysis (SN1) reaction with the fastest rate? c. Which substrate will undergo a SN2 reaction with the fastest rate? d. Which heteroatom has the highest energy HOMO? e. Which acid is the most acidic? f. Which orbital diagram corresponds to the σ* orbital of the C-Br bond? g. Which orbital diagram corresponds to the HOMO of ? C Br C N C Cl C I C O C S H3C Br H3C Br H3C CH3 Br H3C CH3 CH3 CH3 H3C CH3 Br CH3 CH Br 3 H3C Br H3C Br H3C CH3 Br H3C Br CH3 CH3 H3C CH3 Br N O P S Cl N O H O O H H O H CH3 O H C Br C Br C Br C Br • 4 h. Which conformer maximizes the number of σC-H to σ*C-F stereoelectronic interactions? i. Which chair conformation is the most stable? j. Which orbital diagram best represents the π system of a carbonyl? k. Which isomer is achiral due to a point of inversion? l. Which isomer is chiral? H3C Br H3C Br CH3 Br CH3 Br C O C O C O OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH OH 5 Problem 2. For each heterocycle below indicate the hybridization state (sp, sp2 , or sp3 ) of each nitrogen in the ring (40 points; 4 points each). a. f. b. g. c. h. d. j. e. k. N H N H N H N H N H N N N H N H O N N N N N N B H H 6 Problem 3. The following are equilibrium reactions. For each one circle the correct arrow indicating which way the reaction will be most favorable (32 points; 4 points each). NH3 + CH3O NH2 O2N + NH2 CH3O NH3 + O2N + CH3 CH3 O + N(CH3)3 CH3 + H-N+ (CH3)3 CH2 O CH3 O OCH3 O + CH3O Na+ CH3 O OCH3 O + CH3OH H 3. (a) (21) The following are equilibrium reactions (acid-base and others). For each one circle the correct arrow indicating which way the reaction will be most favorable. Example: Na+ H-NH2 + Na NH2 + H2O + - OH Na+ Last Name H3N + OH O + O Na+ O H3N + O Na+ O OH O + OH Me2N O Na+ + O Na+ Me2N OH + CH3 CH3 O + Cl HO OH CH3 CH3 + Cl HO OH O N N H + N N H + N CH3 CH3 N CH3 CH3 + + a) b) c) d) e) f) g) 7 Problem 4. For each of the molecules depicted below, draw any additional resonance structures (one or more) that are chemically important to understand the molecular or electronic structure of each species (36 points; 6 points each). a. b. c. d. e. f. O H3C O O2N O N CH3 O 8 Problem 5. Identify the symmetry elements that make each of the cyclobutanes below achiral (12 points; 4 points each). a. b. c. Problem 6. Label the following alkenes as either E or Z (12 points; 4 points each). a. b. c. OEt O O Se Br 9 Problem 7. Predict the major product of the following reactions. If more than one product is formed show all of them and indicate the major product. Indicate stereochemistry where necessary (20 points; 5 points each). a. b. c. d. OTs OH CH3CN (solvent) CH3 CH3 D H Br NaOEt HOEt Br Br NaN3 acetone (solvent) H3C H3C CH3 H3C Cl KOt-Bu

Solution PreviewSolution Preview

These solutions may offer step-by-step problem-solving explanations or good writing examples that include modern styles of formatting and construction of bibliographies out of text citations and references. Students may use these solutions for personal skill-building and practice. Unethical use is strictly forbidden.

    By purchasing this solution you'll be able to access the following files:
    Solution.pdf.

    $35.00
    for this solution

    or FREE if you
    register a new account!

    PayPal, G Pay, ApplePay, Amazon Pay, and all major credit cards accepted.

    Find A Tutor

    View available Organic Chemistry Tutors

    Get College Homework Help.

    Are you sure you don't want to upload any files?

    Fast tutor response requires as much info as possible.

    Decision:
    Upload a file
    Continue without uploading

    SUBMIT YOUR HOMEWORK
    We couldn't find that subject.
    Please select the best match from the list below.

    We'll send you an email right away. If it's not in your inbox, check your spam folder.

    • 1
    • 2
    • 3
    Live Chats