15. [15 points] (a) Draw the major product(s) expected for the reactions shown below. Indicate stereochemistry in the product when appropriate. (b) Classify each reaction as SN2, SN1, E2 or E1 or a combination of these. (a) CI + (b) (c) محمد H3C x (CH3)3COH NaOH DMSO SH C2H5OH, A Br + Na C2H5 (d) (e) CH31 C2H5OH (CH3)3COH the maior

Give the structures of A to E, showing the absolute stereochemistry in each case.

Complete the following reactions, clearly indicating regio-and stereochemistry where applicable. In cases, where ortho-and para-products are formed, draw both.

What are the major product(s) in reaction a), b), and c)? Be mindful of stereochemistry.

Assign E or Z stereochemistry to each of the following alkenes, and convert each drawing into a skeletal structure (red = 0, yellow-green = Cl). (a) (b)

Predict the product(s) and show the complete electron-pushing mecha- nism for each of the following dissolving metal reductions. (a) H3CC=CCH₂CH3 (b) (c) CECH 1844 Li NH3 ND3 C=C—CH3 NH3

A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a)Rank these three intermediates from most stable to least stable.

Provide the structure of the product(s) with stereochemisty if appropriate. If multiple products indicate major product or if products are formed in equal amounts. If there is no reaction expected explain why. (a) OH HIO4 (the protecting group is remained) CHO H HOH2C OH (b) CHO -ОН NaCN # HO -H H -OH CH₂OH (c) CHO HO- -H HO -H NH₂OH 張一 H -OH H -OH CH₂OH i) Ba(OH)2 ii) MeOH, H₂SO4 NaOAc Ac₂0 NaOMe MeOH

Arrange the alkenes in each set in order of increasing rate of reaction with HI and explain the basis for your ranking. Draw the structural formula of the major product formed in each case. (a) and (b) H3CH₂CHC=CH₂ and (H3C) 2C=CHCH3

Name the following alkyl halides: (a) Hас Br Br CH3 (b) I (c) Br CI CHз CH3CHCHCHCH,CHCH3 CH3CH=CHCH2CHCH3 CH3CCH,CHCHCH3 CH3 (d) CH2BR (e) CICH2CH2CH2C=CCH2B CH3CH2CHCH2CH2CH3