3,5-dinitrobenzoyl chloride. Br 2,4-dibromoaniline. 4-ethylpyridine N COOH CHO CH 2 OH

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1 1. (20 points) Structure and omenclature Draw structures for which names are given and name the given structures by any accepted system (2 points each) a) l 3,5-dinitrobenzoyl chloride b) benzamide c) acetic anhydride 2 d) 2,4-dibromoaniline 3 3 e) ethylpyridine f) cyclohexane carboxylic acid g) dimethyl terephthalate 3 3 h) aminopropanoic acid, 3-aminopropionic acid, β-aminopropionic acid i) j) glucose ( 3 ) ,-dimethylaminoazobenzene

2 2. (6 points) Physical Properties A. (3 points) In the following group of compounds, circle the strongest base. 2 2 B (3 points) In the following group of compounds circle the strongest acid l l 3. (70 points) Reactions Draw the structures of the major organic product(s) of the following reactions (3 points each) 1) P a) 3 2) 2 b)l 2 3 l l 3 c) Mgl 1) 3, ether 3 2) 3 + d) 1) 2) LiAl 4 2 2

3 e) 3 1) B 3, TF 2) 2 2, a 3 f) 3 1) 2 2, 3 + 2) g) r 3 /pyridine 2 h) 3 1) Sl ) I 1) a 2 i) 2)aI, 60 o 2 j) 1) a 2 2) ( 3 ) 2 ( 3 ) 2 B. (40 points) List the reagents which will accomplish the following transformations. More than one step may be required. (4 points each) a) 3 3 l b) 2 LiAl 4

4 c) 3 +, heat d) 2 6 5, e) peracid or /a f) 3 Pl 3 or Sl 2 l 3 g) 2 1) 2 2) 3 +, heat h) ) g(ac) 2, 3 2) ab 4 i) 1) Mg, ether 2) 3 3) 3 + 1) 2, P j) = 2) 3 +

5 4. (24 points) Reaction Mechanisms (8 points each) Draw all of the intermediates form between the starting material and the product in the following reactions: a) 2-2, - heat b) c)

6 5. (18 points) Provide an Example of each of the following (Draw structures) (3 points each) a) An aromatic amine 2 b) a pesticide l l 3 l c) a pheromone d) a naturally occuring carboxylic acid 3 ( 2 ) 7 =( 2 ) 7 e) a stable hydrate of an aldehyde l 3 f) a fat 2 2 ( 2 ) 12 3 ( 2 ) 12 3 ( 2 ) 12 3

7 6. (24 points) Spectroscopic Identification Draw the structures of compounds A and B whose molecular formula and information about the IR and MR spectra are given. Assign the protons in your structure to the MR signals and indicate what information you gained the listed IR absorptions. (12 points each) a) ompound A Molecular Formula: 9 13 IR Spectrum Absorption peaks present above 1600 cm -1 Frequency (cm -1 ) Strength of absorption 3200 weak moderately strong 1600 weak IR indicates at 3200 no carbonyl stretch b) ompound B b d c e a MR Spectrum chemical multi- integration shift (δ) plicity a multiplet b c d e singlet quartet singlet triplet Molecular Formula: IR Spectrum Absorption peaks present above 1600 cm -1 Frequency (cm -1 ) Strength of absorption 3000 broad, weak 2800 sharp, weak 2700 sharp, weak 1701 strong 1600 moderately strong IR indicates no, possible aldehyde at 2700, carbonyl stretch MR Spectrum chemical multi- integration shift (δ) plicity a b c a singlet multiplet singlet c 3 b

8 7. (32 points) Synthesis Show reactions for the synthesis of 4 of the following 6 compounds the indicated starting materials and any inorganic reagents required. (8 points each) a) 2 2, P 3, 2 1) K 2) 3) 2 2, b) and + All 3 2 2, - Sl 2 All 3 l c) 2 2 Sn/l 2 a2, 3 + u, - 3 +

9 d) excess ( 3 ) ( 3 ) 3 - Ag 2, heat e) 2 2 2, Fe S 4, a P f) S 4,

10 8 (24 points) Synthesis (12 points each) A. The spicy flavour of cayenne pepper is due mainly to a substance called capsaicin. Propose a synthesis of capsaicin the indicated starting materials. 2 3 and, 2 capsaicin Mg, ether Mg Sl 2 l B. Lidocaine is an anaesthetic drug. It is synthesized the indicated starting materials. Indicate the steps and reagents you would use to carry out this synthesis. ote that acyl chlorides react faster with nucleophiles such as amines than do alkyl chlorides. 3 2 ( 2 3 ) , l 2 l and ( 3 2 ) 2 lidocaine 3 2 Sn/l 3 2 l 2 l 3 2 l ( 3 2 ) ( 2 3 ) 2 3