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1. Predict the structure(s) of the expected major organic product(s). Unless mentioned otherwise, assume that all reagents are present in excess. Show stereochemistry where needed and write NR if there is no reaction. Write the type of reaction such as SN1, SN2, E1, E2, oxidation, reduction, acid-base etc in the given box. (40 pts) Br C2HgONa, C2H5OH (a) PCC (b) OH o 1) LiAIH4, THF (c) 2) H3O+ (d) t-BuOK, t-BuOH CI (e) CH3CH2OH O 1) CH3CH2MgBr, ether (f) H 2) H3O+ Nal, Acetone (g) OH KCN, DMF (h) 2. Mechanism: Write complete, detailed, stepwise arrow pushing mechanism for the following and draw the stucture of all intermediates. (9 Pts) reaction. Include all steps, show the direction of arrows, write all non-zero charges, CH3OH - -X Br 3. Nomenclature: Give the IUPAC name the following molecule, include absolute stereochemistry if present. (12 pts) a) F CI b) HO Br OH c) 11381 CI 5. Using the following IR and NMR spectra, draw a possible structure for C6H12O in the given box. (10 pts) Degree of unsaturation - Answer IR: 2850cm-¹ and 2750cm medium sharp, 1750 cm-¹ strong sharp. 3H, d 2H, sextet 1H, d 3H, t 1H, 2H, q heptet 9 8 7 6 5 4 3 2 1 PPM 4. (20 pts) Vocabulary: Fill in the blanks with the appropriate word. If two or more words are given, circle the correct one. a) In SN1 reactions of haloalkanes, a leaving group leaves before / after / at the same time as the nucleophile enters and is always / sometimes / never accompanied by an elimination reaction. b) As we go don the periodic table, leaving group ability of atoms increase / decrease. c) Alcohols have higher / lower / same boiling point than haloalkanes of same size because they can form , and they are more / less / same soluble in water than haloalkanes. d) Inductive effect increases as the size of the halogen atom increases / decreases and as the distance between the acidic proton and the halogen increases / decreases. As inductive effect increases, the acid becomes weaker / stronger / unaffected. e) Alkyl and hydride shifts always / sometimes / never happen in SN2 reactions. f) In E2 eliminations, strong bulky bases tend to form Hofmann / Saytzev product, which is the more / less substituted alkene product. g) Molecules that are superimposable mirror images are chiral / achiral. The relationship between these kind of molecules is enantiomers / same meso / diastereomers. h) In SN1 reactions, if we start with an optically active haloalkane, the stereocenter in the product becomes racemic / inverted / retained. atoms or the i) In organic chemistry, oxidation is defined as the removal of addition of atoms to a molecule. j) For an E2 reaction to happen the leaving group and a hydrogen atom must be to one another. functional group k) In aqueous media, primary alcohols are oxidized to a(n) . while secondary alcohols are oxidized to a(n) 5. Identify Enantiomers the relationship (E), Diastereomers between (D), the Identical following Chiral molecules (I) and as Same Constiutional Meso (M). Isomers (9 pts) (C), H CI CI OH HO H a) H3C Br H Br H CH3 CH3 F b) CH3 F CI c) CI CI

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