10. Give the structures for compounds E and F in the sequence of reactions shown below. (2 points) Compound E 1. NaNH2, NH3 2. CH₂CH₂Br Compound F H₂O, H₂SO4 HgSO4

Rank the following carbonyls according to their electrophilicity (1 = most) OEt O of O NEt₂ O CF3 O

e 9) Consider each of the following reactions. Each reaction shown is a reaction between the negatively charged portion of one molecule reacting with the positively charged portion of the other molecule. Circle the negatively charged portion of one reactant and the positively charged portion of the other reactant. (0.5 pt per circle/square) example) (A) (B) Br H₂C H OH CI OH H3C CH₂ A OH -1 (C) (D) Прово شکر H-Br ~1/2

3. Propose a mechanism for the following Sn1 reaction. Include structure for the carbocation intermediate. (0.5pts) o CI NaBr EtOH ∞or Br + NaCl

For the reaction sequence shown in the picture, give the structures for unknown compounds E thru H:

Given the following table of bond dissociation energies (in kcal/mol), what is AH° for this reaction? (CH3);С —Н + Br -Br (CH);С — Br + Н—Br | CH3-H 105 (CH3)3C-H 91 CH3-Br 70 (CH3)3C-Br 65 Br-Br 46 H-Br 88 O +7 kcal/mol O -7 kcal/mol O +16 kcal/mol O -16 kcal/mol O cannot be determined with this information

The best way to accomplish the following reaction is: CH3 x CH3 (a) Hg(OAc)2, H₂O; NaBH4, HO™ (b) BH3 THF; H₂O₂, HO OH CH3 CH3 (c) H+, H₂O (d) 1. MCPBA; 2. H3O+

What are the reagents used and why? (Options for each reaction below) Can you please explain thoroughly how they affect the reactions and when they should be used? Options for a) MCPBA H202,NaOH Conc H2S04, heat HC(triple bond)CNa BH3THF NaOET NBS, heat Options for b) BH3THf MCPBA PCC, CH2CL2 H202,NaOH Conc. H2SO4, heat HC(triple bond)CNa Options for c) Conc. H2S04, heat MCPBA H2O2, NaOH HC(triple bond)CNa NBS, heat PCC, Ch2Cl2

4. Show how the following synthesis could be performed. (9 points) Br ??? Br

Identify the reagents needed to come up with the given compounds. Pls Separate the reagents with a comma and a space. (ex. HNO3, H2SO4). For a multi-step reaction, separate the reagents with a semi-colon. (ex. HNO3, H2SO4; CH3Cl, AlCl3) There should be 9 reagents