Alkyl Halide Chemistry

Can you specify if these reactions produce a primary, secondary or tertiary halide, a vicinal or geminal dihalide or other product?

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ethyl isopropyl ether + excess HBr and heat

1-hydroxy-2-methylcyclohexane + HBr

1-propanol + KBr

1-tosylbutane + NaI

hex-1-ene + HBr

hex-1-ene + HBr and H2O2 and light

cyclohexane + I2 and light

t-butanol + PBr3 and pyridine

2-hexyne + 1 equiv. Br2 in CCl4

ethanol + SOCl2 and pyridine

cyclohexane + NBS (N-bromo-succinimide) and light

Methylcycloxexane + Br2 and light

(Z)-but-2-ene + Br2 in H2O

(E)-hex-3-ene + Br2 in CCl4

diethyl ether + excess HI and heat

3-methylbut-1-ene + HCl

1-hydroxy-1-methylcyclohexane + HI

2-iodopentane + KBr in acetone

1-hydroxy-1-methylcyclohexane + P and I2

dimethylpropane + Cl2 and light

2-hexyne + 2 equiv. HCl

2-hexyne + 2 equiv. Br2 in CCl4

methylpropene + Cl2

1-hydroxy-2-methylcyclohexane + PBr3

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