Question

Each of the following syntheses may require more than one step. Provide the reagents and intermediates for each step from the starting reagent to the final product.

H H and prepare CH3CH-CH2 (a) Start with CH3 CH3 and prepare (b) Start with OC(CH3)3 and prepare and any 2 carbon fragment (c) Start with CH3CH CH2 СH, and prepare (d) Start with

Answer 1

C (H- CHCC - CH₂ Br@ ONH₂ Br - H CH3 H Br KNH₂ Nalth CH₂-CEC-H KNH2 CH₂ - C = C -+ Br CH₂ - C = CO Na CH₂-CEC- CH3 CHIT H2 & Pd-e HA Cld HC product

b) this reaction proceeds through SN1 pathway.

b) (CH₂), CONA EtOH (CH3) Coo da oc(CH₂)2 product

CRO-OR HARRO ROB ROH & Br CH, CH = Hen CH - CH = CH - P. nr Br Bry CH2-CH - CH, Ba Н 124 . CH₂ - CH₂ - Chagli CH₂ - CH₂ - CH₂ CH₂ - Catz-en t = i product

Br Po=0 NBS 24 сни ho CH3 11 CH₂ I 2 H2 zn Simmon-smith Zn-I reeaction СңІ, +Zn 11111 product