write a step by step mechanism for the following reactions. Indicate the major a

Question

write a step by step mechanism for the following reactions. Indicate the major and minor products (if any) N-bromosuccinimide (uv light) 1. benzene-CH=CH-CH3 -----------------------------------------> Product? (leave out mechanism) CH3OH 2. cyclohexene-CH2-Br -------------------------------------------> cyclohexene-CH2-OCH3 (I), cyclohexene=CH3 (II), cyclohexene=CH3 and OCH3 (on adjacent carbon) (III) H2SO4(aq) Catalyst 3. cyclohexane-OH -------------------------------------> cyclohexene (I) + cyclohexane-O-cyclohexane (II) CH3OH (heat) 4. cyclohexane-CH2I -----------------------------------------> cyclohexane-CH3 and OCH3 (on same carbon) (I) + cyclohexane-OCH3 (II)

Explanation / Answer

1.) benzene-ch=ch-ch2br.................... 2)cyclohexene-ch2br + [H+]----->cyclohexene-ch2^+ [HBr],,,,,,,then attack of CH3O- on the carbocation..forms cyclohexene-CH2-OCH3,,,,,,,,,(I) carbocation rearrange ment..positive charge will shift to tertiary carbon on reaction with CH3OH forms cyclohexene=CH3.. follwed by elimination reaction (II)....similarly next positive charge shift to secondary carbon w.r.t to tertiary carbon & follows substitution with CH3O- forms cyclohexene=CH3 and OCH3 (on adjacent carbon),,,,,,,,,3) cyclohexane-OH + {H+} fromH2SO4(aq) Catalyst attacks on OH and remove water to form cyclohexane carbocation & then removal of Hydrogen from adjacent carbon to form cyclohexene (I),,,,,,,,cyclohexane carbocation + cyclohexane-OH gives on removal of {H+} gives cyclohexane-O-cyclohexane (II)....,,,, 4)cyclohexane-CH2I-... first iodine will remove to forma primary carbocation ..then rearrangement primary to tertiary..then attack of (CH3O-} to give cyclohexane-CH3 and OCH3 (on same carbon)

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