1. For each compound, label the chemical equivalent hydrogens. Include cis-trans hydrogens on rings when they are inequivalent. Example: -CH₂ H₂C X H₂C 8 t CH₂ CH₂CH₂ CH₂ VEM

Name the following ethers. Use -oxy if groups on either side of -O—are too complicated.

9.

Rank the molecules A to D shown below by decreasing reactivity towards lodo cyclohexane. H3C-CH,OH F,C-CH,OH H,C-CH,NH, H3C-N-CH, A в D O 1.C>D>A>B O 2.B> A> C> D O 3. A> C> B > D O 4. A> B>D>C

Rank the following compounds in order of increasing acidity: HO- HO- HO HO- ČH3 NO2 CI I II III IV

5) Use arrow pushing to explain the following reaction: NH4 + NH3 H3C CH2 H3C CH3

1. Which compound is more soulable in water : CH3 CH2 CH2 CH2 CH2 CH3          OR CH3 CH2 CH2 CH2 COOH 2. Which compound is more soulable in organic solvent  : CH3 CH2 CH2 CH2 CH2 CH3          OR CH3 CH2 CH2 CH2 COOH

Four isomers A-D with the formula C5H12O exhibit different reactivity patterns as indicated below. Isomer A reacts with PCC and CrO3 to provide identical products.   Isomer B reacts with PCC and CrO3 to provide different products.   Isomers C and D do not react with either PCC or CrO3.   Isomers A, B, and C readily react with NaH but D does not show any reactivity with NaH.     The 1H NMR splitting patterns for these isomers are as follows.     Isomer A: δ 0.91 (d, 3H), 0.90 (d, 3H), 1.18 (d, 3H), 1.92 (dqq, 1H), 3.38 (dq, 1H), 3.58 (bs, 1H). Isomer B: δ 1.25 (s, 9H), 3.45 (s, 2H), 3.65 (bs, 1H). Isomer C: δ 0.90 (t, 3H), 1.44 (q, 2H), 1.24 (s, 6H), 3.65 (bs, 1H). Isomer D: δ 1.10 (t, 3H), 1.13 (d, 6H), 3.19 (septet, 1H), 3.50 (q, 2H).   Based on all of this information, provide the structures of A-D.  (Note: If there is a chiral center on any of these molecules, assume the stereochemistry as “R”.  dqq=doublet of a quartet of a quartet, bs=broad singlet)