substitution and elimination

Question 1

straight chain primary substrate with very weakly basic nucleophile (H2O, alcohol ROH, PR3)

Answer 1

Sn2

Question 2

branched primary substrate with very weakly basic nucleophile (H2O, ROH, PR3)

Answer 2

slow Sn1
not Sn2 bc steric hindrance
slow bc carbocation will rearrange

Question 3

straight chain secondary substrate with very weakly basic nucleophile (H2O, ROH, PR3)

Answer 3

Sn2

Question 4

branched secondary substrate with very weakly basic nucleophile (H2O, ROH, PR3)

Answer 4

Sn1

Question 5

tertiary substrate with very weakly basic nuckeophile (H2O, ROH, PR3)

Answer 5

Sn1 with minor E1

note: Sn1 always accompanied by minor E1

Question 6

primary substrate with moderately basic nucleophile (RS-, NC-, RCOO-, X-)

Answer 6

Sn2

Question 7

secondary substrate with moderately basic nucleophile (RS-, NC-, RCOO-, X-)

Answer 7

Sn2

Question 8

tertiary substrate with moderately basic nucleophile (RS- NC-, RCOO-, X-)

Answer 8

Sn1 with minor E1

note: Sn1 always accompanied by minor E1

Question 9

primary substrate with strongly basic nucleophile (H2N-, R2N-, HO-, RO-)

Answer 9

Sn2

Question 10

secondary substrate with strongly basic nucleophile (H2N-, R2N-, HO-, RO-)

Answer 10

E2 with minor Sn2

Question 11

tertiary substrate with strongly basic nucleophile (H2N-, R2N-, HO-, RO-)

Answer 11

E2

Question 12

primary, secondary, tertiary substrate with bulky and strongly basic nucleophile ((CH3)3CO-, [(CH3)2CH]2N-)

Answer 12

E2