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PART-I: Vocabulary. Fill in the blank with the appropriate vocabulary word. If two or more words are given, circle the correct one. (30 pts) A) Radical bromination has a late / early transition state, is faster / slower and endothermic / exothermic than radical fluorination. B) If there are more than one stereocenters in a molecule, the molecule as a whole is sometimes / always / never chiral. If there is only one stereocenter in a molecule, the molecule as a whole is sometimes / always / never chiral. C) In electrophilic addition reactions, the alkene acts as a(n) electrophile / nucleophile, D) In free radical addition of H-X to alkene HCI / HBr / HI is the only one that works and the product follows Markovnikov / Anti-Markovnikov rule. E) KMnO4 reacts with alkene to give syn diols when diluted and cold / concentrated and hot. It gives oxidative cleavage products when diluted and cold / concentrated and hot. F) In the indirect hydration of alkenes with oxymercuration-demercuration, the reaction proceeds through Anti-Markovnikov / Markovnikov with syn / anti addition of H and OH. G) Electrophiles are always / sometimes / never Lewis bases while Nucleophiles are always / sometimes / never Lewis acids. H) In SN2 reactions, the nucleophile attacks the substrate from the front / back / either side, and the product will have retention / inversion / racemization of stereocenter. I) The overlap of neighboring orbitals to stablize radicals and carbocations is called . This makes 3°/2°/1° radicals the most stable radicals. J) On IR spectrum, the region between 2750 and 3650 cm-¹ corresponds to X-H / double bond / triple bond. K) In E1 reactions, the hydrogen and the leaving group must be syn / anti / either for the reaction to happen. L) A(n) effect is a scenario where halogens near an alcohol withdraws electron density from the conjugate base. This makes the acid stronger / weaker because of the halogens stablize / destabilize the conjugate base. M) Jones reagent oxidizes secondary alcohols to aldehyde / ketone / carboxylic acid. N) When primary alcohols are reacted with nucleophilic acids such as HI and HBr, they will undergo SN1 / SN2 / E1 / E2 reaction. O) Nucleophiles attack the least / more substituted side of epoxides when the reaction is run under acidic conditions. P) During an oxidative cleavage with hot and conc. KMnO4, the alkene carbon if di-substituted becomes a(n) , if mono-substituted becomes a(n) ; and if non- substituted becomes a(n) functional groups. Q) Nucleophilicty increases / decreases / remains the same and the acidity of a molecule increases / decreases / remains the same as we go from left to right on the periodic table and. PART II. Nomenclature: (25 pts) Give the IUPAC name for the following compounds or draw the correct structure for the given names. Use absolute stereochemistry (R, S, E, Z) where appropriate. OH A) in -0 Br B) OH C) O Br D) (7R,8S,E)-7,8-dibromo-3-ethyl-4-methylnon-4-ene E) (6R)-2-(1-bromoethyl)-4,4-diethyl-6-(1-ethylpropyl)cycloheptan-1-ol Part III: Short answers. i) Give the hybridization of the indicated atoms as SP, SP2, SP³ or unhybridized. (10 pts) H A) F) J HO N G B) G) HN H C) H) A F B F D) I) O E C D E) J) ii) What is the shape (geometry) at the indicated carbon above? (3 pts) A) C) I) iii) How many chiral carbons are present in the above molecule? (1 pt) all reasonable structures of the following molecules. Include charges and iv) Draw resonance electron movement arrows. Circle the most stable resonance structure. (7 pts) O v) Select the appropriate compound(s) using letter codes for the catagories below. Some compounds may be used more than once, and some may not be used at all. (11 pts) (+ H2O BF3 H Nal + HCI Br A B C D E F G H Electrophilic carbon: Nucleophile: Lewis Acid: Lewis Base: Bronsted-Lowry acid: vi) Convert the following condensed formulas into their bond line structures. (5 pts) CH3(CH2)4CHOHCCCOOCH(CH2CH3)CCI2(CH3)3 Part III. Short answers continued: vii) For each of the given pairs of molecules, circle the one that is MORE STABLE. If they have equal stability write SAME. Give a brief explanation describing the chemical principle that makes it more stable. (10 pts) a) Vs b) Vs c) Vs H H H H H CH3 d) Vs H H3C H CH3 H CH3 H H H F H Vs e) F H F H F H H viii) Identify the relationship between the following molecules. Possibilities are Same Meso (M), Constiutional Isomers (C), Enantiomers (E), Diastereomers (D) and Identical Chiral (l). (8 pts) OH Br H Br HO H a) Br H H3C H CH3 Br b) OH OH OH OH c) Br. Br Br F Fri, d) Short Answers continued ix) For each of the given pairs or substrates circle the molecule which would result in a faster SN2 reaction if all other factors were the same. In the space provided, state why that molecule would have a faster reaction. (i.e. What fundamental principle causes faster reaction) (12 pts) a) NH3 Vs PH3 as nucleophile b) H2O Vs CH3COCH3 as solvent c) F-Vs Br° in aprotic solvent d) Br Vs Br e) Br Br Vs OH f) OMs Vs x) Look at the given molecules and answer the following questions (8 pts) Br o o H "H H H A H B C D a) How many different chemical environments (number of peaks) would you expect to see in the 1HNMR spectra for each molecule? A= B= C= D= b) Predict how many sub peaks would be seen in the 1HNMR spectrum for the indicated hydrogen due to spin-spin splitting? A= B= C= D= he structure of the major organic product : stereochemistry if applicable. Assume a noted otherwise. If no reaction occurs, w DH H3PO4, H2O heat 3 H NaN3 , HMPA F HI 1) mCPBA, CH2CI2 3 2) CH3OH, H+ 1) PBr3 H 2) t-BuOK, t-BuOH 1) H2. Pd 2) Br2, Au CH3CH2ONA CH3CH2OH Part IV. Reactions continued. Draw the structure of the major organic product(s) formed in t include stereochemistry if applicable. Assume all reagents are otherwise. If no reaction occurs, write NR. (21 pts) h) H-I i) Cl2, CH3OH 1) Hg(OAc)2 H2O j) 2) NaBH4 1) O3 k) 2) / S I) CHBr3, NaOH m) 1) OsO4 2) H2O2 H+, H2O Part V: Mechanism. Write stucture Include complete, all of all of write mechanism all non-zero for charges, the following and reaction. draw the + - .. N=N=CH2, Au or heat VI: Synthesis. Show how you would efficiently synthesize the final molecule (right) from the provided starting material (left). Provide the reagents for each reaction step and draw all resulting products for each step. Note: No arrow pushing mechanism is required to answer this question. (10 Pts) OH o Part VII: Spectroscopy, 6. Using the following spectra, draw a possible structure for C6H12C in the given box. (10 Pts) Degree of Unsaturation = Answer IR: 3300 strong/broad, 3100 strong/sharp and 1600 medium/sharp. 1HNMR 3H, d 3H, S 2H, t 2H, t 1H, q. 1H, br. S 6 5 4 3 2 1 O PPM

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