Show reagents and experimental conditions to bring about the following transformations. H,C C=C H3C CH3 C=C Br H CH3 CH,CHCH3 H' H (h) CH,CCH,CH3 (i) (a) (g) H3C (1) C=C Br CH;CH=CH, CH3C=CCH3 (b) Br CH3 (f) CI CI CI CI CH;CHCH, CH,C=CH (d) CH3C=CH, (e) CH;CCH3 CI

11. Plan syntheses of the following compounds. You may use the given starting material and any compound containing five or fewer carbons. (a) MeO MeO CN TOXXON anything with five or fewer carbons. CN (b) (c)

Which of the following is a major product of the reaction sequence below? Br (1) HNO3/H,SO4 NO2 Br (A) H3CO. (B) H3CO (2) Na CH,0 CH:OH OCH3 Br NO2 Br (D) (C) OCH3 NO2 Compound C O Compound B Compound D Compound A

Alkenes

Predict the major product(s) of the following reactions. For reactions that are not stereospecific, you should select all correct stereoisomers.

+ H3C- CH₂ - CH2 - COR and have undergone McLafferty rearrangement and Ortho effect respectively. What are the possible fragments obtained as a result of these processes ? COOCH3 OH + (A) [R-CH₂-C (A) R-CH₂-CH₂ - CH₂ - COH @E OH]: [c C6H4 O and CO (B) H₂C=CROH and H₂C = CH₂ [2] : [ C₂H4O3 and CH4 (C) (D) H₂CCROH and C₂H4; [(C6H4O), CO and CH₂OH] RH, C₂H4 and CH₂CO; [(C₂H4O), CO and CH₂OH]

Give the major organic product(s) for the following reaction

What is the expected product of the reaction below: CH3 + CH3-C-Br + Na : CCH CH3 CH3. CH3 CH3 CH3 | CH2 H-C=C-H CH3--C=C-H CH3 CH2 =C-CH3 and CHS II || CH3 H-C=C-CH2-CH-CH3 IV