7 bints eBook O References Be sure to answer all parts. Draw a stepwise mechanism and the product for the following substitution reaction: Hint Guided Soluti H.C- NaOCH3 acetone finish structure draw structure ** OOO I I CHI ۵

3. What is the major organic product obtained from the following sequence of reactions? [4] 1. (CH3)2CHCH2MgBr 2. H₂O OH Et₂O OH || CrO3 H2SO4 IV A) I B) II C) III D) IV

1) Outline reasonable synthetic schemes to convert pentane to 1-tritio-1-butyne 2) Draw a reasonable curved arrow mechanism for the following conversion: Но H;O* OH

CH3 o alengoiga6 916w vtalmedoociote 6. Plan syntheses of the following compounds. You may use the given starting material and any compound containing three or fewer carbons. () (a) Br Br Br (d) of (b) ОН ОН (o) Оама (c) (b). (d) Br C Br ОН (e) CI (e) CI CI CI

Draw the structures of the main organic product(s) formed in the following reactions: i) CH3-C-CI C6HS AICI3 ii) CI H2O/H* w b bon ii) C2H5NH2 iv) CH;NH2 CI v) -CI AICI3 vi) CH2CH3 AICI3 CH3CHCI CH3 CS Sranned withhComScanne

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3) Show how you would synthesize the following Compounds, storting with benzene or toluene ond ASSume any necessory pro duct (ond seperoble from ortho) in ortho, pora reogents, poro is the mogor mixture c)o- chlorobenzoic ocid d) m- chloronitro benzene

Give the best reagents for the reaction. (CH₂)₂2CHCH₂CH₂C=CH H2O, H2SO4, HgSO4 BH3, H2O2, NaOH OK2Cr207 O H2, Lindlar Catalyst (CH;); CHCH;CHỊCHỊCH O

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What is major product formed in the following reaction? CH3 ROOR H3C- C-CH3 HCl + CH3 CH3 H C-CH3 H2 -CH3 (A) H3C- (B) H3C-Ć- CH3 H2 H2 (D) (C) H3C- -C-c-CI No Reaction fu CH