Test 5 (Lecture 5 / Module 5): 5 points 1. For each reaction below, look at the reagents and conditions (above and below the arrow) and draw the final product. Determine if it proceed via: SN1, SN2,...

Assignment attached below.


Test 5 (Lecture 5 / Module 5): 5 points 1. For each reaction below, look at the reagents and conditions (above and below the arrow) and draw the final product. Determine if it proceed via: SN1, SN2, or neither (no reaction) (2 points): (a) (0.4 points): Answer: (b) (0.4 points): Answer: (c) (0.4 points): Answer: (d) (0.4 points): Answer: (e) (0.4 points): Answer: 2. (a) Circle ONLY GOOD LEAVING GROUPS which can be replaced in SN1 or SN2 reactions (0.5 points): (b) Which one is THE BEST LEAVING GROUP (0.5 points): Hint: use the chart on page 151 (Chapter 9.4): Answer: 3. Identify if the following (SOLVENT, SUBSTRATE, NUCLEOPHILE, LEAVING GROUP) are best for SN1 or SN2 reactions or BOTH (2 points): SN1 SN2 SECONDARY (SUBSTRATE) ‒ (example) YES (example) TOSYLATE (OTs) GOOD (LEAVING GROUP) YES (example) YES (example) (NUCLEOPHILE) (SUBSTRATE) (NUCLEOPHILE) (NUCLEOPHILE) (SUBSTRATE) TRIFLATE (OTf) (LEAVING GROUP) (SUBSTRATE) WATER (H2O) (SOLVENT) DMSO (SOLVENT) (SOLVENT) MIDTERM (Lecture 1 – 5 / Module 1 – 5): 20 points 1. Show a mechanism for the acid-base reaction and determine the position of equilibrium. (5 points): (a) (2.5 points) Answer: (b) (2.5 points): Answer: 2. Draw the structures of the following compounds. (5 points): (a) 2-chloro-3-ethyl-2,4-difluoro-4-methylnonane (1 point): (b) 4-ethyl-2,4-dimethylcyclohexa-2,5-dien-1-one (1 point): (c) (Z)-2-bromo-1-chloro-1-fluoroprop-1-ene (1 point): (d) (1R,3R)-3-methylcyclohexan-1-ol (1 point): (e) 3-amino-5-bromo-4-cyclopropyl-2-fluoroheptan-1-al (1 point): 3. (a) Identify the type of hybridization (sp, sp2, sp3) of each atom (C atoms O atoms and N atoms) of the following compound (2 points): sp = BLUE circle or sphere sp2 = GREEN circle or sphere sp3 = RED circle or sphere (b) Identify the type of hybridization (sp, sp2, sp3) ONLY of N (NITROGEN) atoms of the following compound (2 points): 4. Draw a chair conformation, a flipped chair conformation and identify the most stable chair conformation and explain why (6 points): (a) (b) (c) (d) (e) (f) BONUS QUESTIONS: 1. For the compounds below (a) draw both Conjugate Base 1 and Conjugate Base 2. Determine which of the two protons is more acidic using the ARIO rule and explain your reasoning - if the reason is R (number of Resonance Structures) please draw all the resonance structures. Make sure you keep track of all formal charges and lone pairs (1 point): Conjugate Base 1: Resonance: Conjugate Base 2: Resonance: Answer: 2. Answer the questions and fill each box below (total 2 points = 0.1 points x 20 boxes): Find all of CHIRAL centers “Circle or label them if they exist” Is it a MESO form? YES/NO Name each CHIRAL center (R or S if they exist) Draw the ENANTIOMER “if it exists” Remember: meso forms do not have enantiomers Draw a DIASTEREOMER 3. Draw Newman projection for the compound below (2 points): Hint: You have to draw two connected Newman projections. Name: (1S,2R,5S)-2-isopropyl-5-methylcyclohexan-1-ol (A) Newman 1 (1 points): (B) Newman 2 (1 points):