11. Predict the major product obtained when the following compound is treated with Birch conditions: Write a detail mechanism. (8 Points) хоч Na, CH₂OH NH3
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- 8.53 Synthesize the following compound starting with ethyne and 1-bromopentane as your only organic reagents (except for solvents) and using any needed inorganic compounds. Br Br 9-44 How would you prepare cyclodecyne starting from acetylene and any required alkyl halide? 9-42 How would you synthesize the following compounds from acetylene and any alkyl halides with four or fewer carbons? More than one step may be needed. (a) CH3CH2CH2C=CH (b) CH3CH2C=CCH2CH3 CH3 CH3CHCH2CH=CH2 (c) (d) CH3CH2CH2CCH2CH2CH2CH3 (e) CH3CH2CH2CH2CH2CHO8:42 7 ull u 654 Problems Set – Alcohols and Phenols 1. Give IUPAC names for the following compounds: OH OH CHyCHCH,ČHPHCH, (a) (b) он (c) HO. CH;CH;CCH3 CHa ČH3 CHa CH (d) H. (e) H3C. (T) осна Br Br OH 2. Identify the alcohols in Problem 1 as primary, secondary, or tertiary. 3. Draw structures corresponding to the following IUPAC names: (a) 2-Methylhexan-2-ol (c) 2-Ethylbut-2-en-1-ol (e) o-Bromophenol (b) Нехаne-1,5-diol (d) Cyclohex-3-en-1-ol (f ) 2,4,6-Trinitrophenol 4. What carbonyl compounds give the following alcohols on reduction with LIAIH4? Show all possibilities. (b) он CHCH3For alkenes A, B, and C: (a) Rank A, B, and C in order of increasing heat of hydrogenation; (b) rank A, B, and C in order of increasing rate of reaction with Hạ, Pd-C; (c) draw the products formed when each alkene is treated with ozone, followed by Zn, H,0. A. B
- 8.108 Propose a plausible mechanism for the following transformation, which was used as the key step in the formation of the natural product heliol.2. Identify the major product in each of the following reactions: (5 pts) (a) НА (b) НА он (c) CH,CH,NH, (d) HCN (e) KMNO,(a) Rank the following carbocations in order of increasing electrophilicity (1 = lowest electrophilicity, 4 = highest electrophilicity). (b) Rank the following 1,1-halomethylcyclopentanes in order of reactivity in an SN1 reaction (1 = lowest reactivity, 4 = highest reactivity. CH3 CI B with SNI, nor reactive means more stable (c) Rank the following species in terms of increasing nucleophilicity in an SN2 reaction in a po aprotic solvent (1 = lowest nucleophilicity, 4 = highest nucleophilicity).
- 12.60 Predict the major product of the following reaction. Mof O-S (a) (c) CN OUS=O 7 NaCN acetone (b) (d) ? CN4. (40 pts) Provide the bond line structure and IUPAC name for the major organic product obtained in each step: HBr (1R, 2S) 1,2,2-trimethyl- ---------> A 6-phenylcyclohexanol KOtertBu HOtertBu HBr peroxides Mg ether ethylene oxide H₂O B > C D E Product Bond line structure IUPAC nameExplain why the addition of bromine to compound A gives a product in which the two bromine atoms occupy equatorial positions, whilst the addition of bromine to compound B gives a product in which the two bromine atoms are in axial positions. (2 pts) H H I A B