Rank the molecules A to D shown below by decreasing reactivity towards iodo cyclohexane. H;C-CH,OH F3C-CHOH H,C-CH,NH, H3C-N-CH, A в O 1.C> D> A>B O 2.B> A> C> D O3. A>C>B> D O 4. A> B> D>C

2. For the following nucleophilic substitution reaction: NaOC(CH3)3 CH3 'CH3 CH3 a. Draw the first transition state (TS1), the reaction intermediate, and the second m transition state (TS2) in the labeled boxes. Make sure to show any formal charges, unfilled p-orbitals, and correct stereochemistry. TS₁ 41001 Intermediate ogmos TS2 amond- b. Which of three molecules you drew for part 'a' is lowest in energy? Write your answer in the box below. c. Draw the product(s) of the nucleophilic addition reaction shown. Make sure to use wedged and dashed lines to clearly show the resulting stereochemistry at each chiral center. If there is more than one possible product, draw one in each box - if not, leave one box blank. CH3 Br + NaOC(CH3)3

are these correct?

9. Draw the constitutional isomer formed when the following alkenes are treated with each set of reagents: [1] H20, H2SO4; or [2] BH3 followed by H2O2, "OH. A io onutouTC.rvinmmoo ewo ebyoleen.g er besibhoyn motis M doso al waH s b. a. Seblaar molsHsno isq onol nose 2eob isticho to eqyt ewni.d Cnistnoo ennug 29ob anodogle yoam woH.o O bns 18 to alnemala erlT nertw bemot witam-S ae doue anexie leohtemmyeni

What are the expected major products, X & Y, upon reaction of HBr with the alkene shown under two different conditions indicated? HBr, ROOR Y HBr heat Br Br Br II Major productX= choose your answer. ^ Major product Y= choose your answer... choose your answer... II II

Show how the reactions take place. Concert the ff condensed formula into structural formula. 1. сН3-CН2-СH2-CH2-CH-CHЗ + кон 2. СНЗ-СН2-СH-CH2-CH2-CHз H+ A 3. CH3-CH2-CH2-CH=CH3 + I2

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

Predict the dehydrohalogenation product(s) that result when the following alkyl halides are heated in alcoholic KOH. When more than one product can be formed, rank them in terms of their predicted stability (1 is most stable isomer, 2 the next most stable isomer, etc...) a) b) HD HD H CH3 ''CI H CH3 Br 'Br KOH EtOH KOH EtOH KOH EtOH

8. a. Assign E or Z configurations to each alkene below. H₂C Br CH3 CH₂CH3 b. CH3 CN CH₂CH₂OH

1. What are products of the following reaction: ÇH2-O-CO-(CH2)7-CH=CH-(CH2)7-CH3 ҫн-0-СО-(СH2)7-CH-CH-(СH2)7-CНЗ СH2-0СО-(СH2)16-СНЗ 2H2 Ni